HALOGEN CONTAINING COMPOUNDS

Introduction of Halogen containing compounds

Q.1 How many structural isomers are possible for a compound with
molecular formula C3H7Cl
(a.1) 2 (b.1) 4 (c.1) 7 (d.1) 9
Q.2 In CH3CH2Br, % of Br is .....
(a.2) 80 (b.2) 75 (c.2) 50 (d.2) none of these
Q.3 Gem- dibromide is ......
(a.3) CH3CH(Br)OH(Br)CH3 (b.3) CH3CBr2CH3
(c.3) CH2(Br)CH2CH2 (d.3) CH2BrCH2Br
Q.4 Ethylidene dibromide is....
(a.4) CH3 -CH2 -Br (b.4) Br -CH2-CH2 -Br
(c.4) CH3 -CHBr2 (d.4) CH2= CBr2
Q.5Benzylidene chloride is .....
(a.5) C6H5CH2Cl (b.5) C6H5CHCl2
(c.5) C6H4ClCH2Cl (d.5) C6H5CCl3
Q.6 Which of the following halide is 2......
(a.6) Isopropyl chloride (b.6) Iso-butyl chloride
(c.6) n-propyl chloride (d.6) n-butyl chloride
Q.7 Haloforms are trihalogen derivatives of .....
(a.7) Ethane (b.7) Methane (c.7) Propane (d.7) Benzene
Q.8 Benzene hexachloride is ...
(a.8) 1, 2, 3, 4, 5, 6-hexachlorocyclohexane
(b.8) 1, 1, 1, 6, 6, 6-hexachlorocyclohexane
(c.8) 1, 6-phenyl-1, 6-chlorohexane
(d.8) 1, 1-phenyl-6, 6-chlorohexane
Q.9 Number of -bonds present in B.H.C. (Benzene hexa chloride) are ..
(a.9) 6 (b.9) Zero (c.9) 7 (d.9) None of these.
Q.10 The general formula for alkyl halides is....
(a.10) CnH2n+1X (b.10) CnH2n+2X
(c.10) CnHn+1X (d.10) CnH2nX
Q.11 Which of the following is a primary halide....
(a.11) Isopropyl iodide (b.11) Secondary butyl iodide
(c.11) Tertiary butyl bromide (d.11) Neo hexyl chloride
Q.12 Full name of DDT is
(a.12) 1, 1, 1-trichloro-2, 2-bis(p-chlorophenyl) ethane
(b.12) 1, 1-dichloro-2, 2-diphenyl trimethylethane

(c.12) 1, 1-dichloro-2, 2-diphenyl trichloroethane
(d.12) None of these
Q.13 The compound which contains all the four 1,2,3 and 4 carbon atoms
is....
(a.13) 2, 3-dimethyl pentane
(b.13) 3-chloro-2, 3-dimethylpentane
(c.13) 2, 3, 4-trimethylpentane
(d.13) 3, 3-dimethylpentane
Preparation of Halogen containing compounds
Q.14 The following reaction is known as.........

Pyridine
2 5 2 2 5 2
C H OH SOCl C H Cl SO HCl + + +
(a.14) Kharasch effect
(b.14) Darzens procedure
(c.14) Williamsons synthesis
(d.14) Hunsdiecker synthesis reaction
Q.15 What is the main product of the reaction between 2-methyl propene
with HBr.....
(a.15)1-bromo butane
(b.15) 1-bromo-2 methyl propane
(c.15) 2-bromo butane
(d.15) 2-bromo-2 methyl propane
Q.16 Halogenation of alkanes is
(a.16) A reductive process (b.16) An oxidative process
(c.16) An isothermal process (d.16) An indothermal process

Q.17 In the above process product A is ......
(a.17) Fluorobenzene (b.17) Benzene
(c.17) 1, 4-difluorobenzene (d.17) 1, 3-difluorobenzene
Q.18 Silver acetate
2
CS
2
Br + . The main product of this reaction is.....
(a.18) CH3 -Br (b.18) CH3COI (c.18) CH3COOH (d.18) None of these
Q.19 Diazonium salts +Cu2Cl2+ HCl , the reaction is known as.....
(a.19) Chlorination (b.19) Sandmeyers reaction

(c.19) Perkin reaction (d.19) Substitution reaction
Q.20 When ethyl alcohol (C2H5OH) reacts with thionyl chloride, in the
presence of pyridine, the product obtained is......
(a.20) CH3CH2Cl +HCl
(b.20) C2H5Cl+HCl+SO2
(c.20) CH3 CH2Cl+ H2O+SO2
(d.20) CH3 CH2Cl+HCl+ SO2
Q.21 Preparation of alkyl halides in laboratory is least preferred by........
(a.21) Treatment of alcohols
(b.21) Addition of hydrogen halides to alkenes
(c.21) Halide exchange
(d.21) Direct halogenation of alkanes
Q.22 Which of the following organic compounds will give a mixture of 1-
chlorobutane and 2-chlorobutane on chlorination .......
(a.22)
3 2
|
3
CH CH CH CH
CH
=
(b.22)
|
2
H
HC C C CH =
(c.22) CH2=CH-CH= CH2
(d.22) CH2=CH -CH2 -CH3
Q.23 The chlorobenzene is generally obtained from a corresponding
diazonium salt by reacting it with .......
(a.23) Cu2Cl2 (b.23) CuSO4 (c.23) All of these (d.23)
2
3 4
Cu(NH )
+

Q.24 Decreasing order of reactivity of HX in the reaction
ROH + HX RX+ H2O
(a.24) HI > HBr > HCl > HF (b.24) HBr > HCl > HI > HF

(c.24) HCl > HBr > HI > HF (d.24) HF > HBr > HCl > HI
Q.25 The product of the following reaction : CH2 = CH - CCl3 + HBr
(a.25) CH3 - CH(Br)- CCl3 (b.25) CH2(Br) - CH2 - CCl3
(c.25) BrCH2- CHCl CHCl2 (d.25) None of these.

#2# % of Br
Mass of Br
100
Mass of organic compound
=


80
100 73.39%
109
= = or approx. 75%
#3# Gem-dihalides are those in which two halogen atoms are attached on
the same carbon atom.

#6# Isopropyl chloride
o
2
3 3
|
CH CH CH
Cl
chlorine atom is attached to 2
carbon atom.
#7#
3H
4 3
3X
CH CHX

+
(X = Cl, Br, I)
#11# Neohexyl chloride is a primary halide as in it Cl-atom is attached to a
primary carbon.

3
|
3 2 2
|
3
CH
CH C CH CH Cl
CH


#12#


13. (b)
o o
o o o
o
o
1 1
3 3
1 | | 2 1
3 2 3
3
4 |
3-chloro-2,3-dimethylpentane
CH CH
CH CH C CH CH
Cl

#15#
|
3 2 3 3
| |
3 3
2-bromo, -2-methyl propane
Br
CH CH CH HBr CH C CH
CH CH
= +
#18# CH3COOAg + Br2
2
CS
CH3Br + AgBr +CO2
#20# C
2
H
5
OH+SOCl
2

Pyridine
C
2
H
5
Cl+SO
2
+HCl


Testtwo
Q.26 Chlorobenzene is prepared commercially by
(a.26) Raschig process (b.26) Wurtz Fitting reaction
(c.26) Friedel-Crafts reaction (d.26) Grignard reaction
Q.27 In methyl alcohol solution, bromine reacts with ethylene to yield
BrCH2CH2OCH3

in addition to 1, 2-dibromoethane because
(a.27) The ion formed initially may react with Br
-
or CH3OH
(b.27) The methyl alcohol solvates the bromine

(c.27) The reaction follows Markownikoff's rule
(d.27) This is a free-radical mechanism
Q.28
Light
3 8 2 3 7
C H Cl C H Cl HCl + + is an example of which of the following
types of reactions.......
(a.28) Substitution (b.28) All of these
(c.28) Addition (d.28) Rearrangement
Q.29 Which of the following would be produced when acetylene reacts with
HCl
(a.29) CH3CH2Cl (b.29) CH3CHCl2
(c.29) CHCl = CHCl (d.29) CH2 = CHCl
Q.30 R-OH+HX R-X+H
2
O
In the above reaction, the reactivity of different alcohols is
(a.30) Tertiary > Secondary > Primary
(b.30) Tertiary < Secondary < Primary
(c.30) Tertiary < Secondary > Primary
(d.30) Secondary < Primary < Tertiary
Q.31C6H6 + Cl2
UV Light
Product. In above reaction product is
(a.31) CCl3CHO (b.31) C6H6Cl6
(c.31) C6H12Cl6 (d.31) C6H9Cl2
Q.32 Benzene reacts with chlorine to form benzene hexachloride in presence
of
(a.32) Nickel (b.32) AlCl3
(c.32) Bright sunlight (d.32) All of these
Q.33 The final product obtained by distilling ethyl alcohol with the excess of
chlorine and Ca(OH)2 is .......
(a.33) CH3CHO (b.33) CCl3CHO
(c.33) CHCl3 (d.33) (CH3)2O
Q.34 When ethyl alcohol and KI reacted in presence of Na2CO3. yellow
crystals of...... are formed
(a.34) CHI3 (b.34) CH3I
(c.34) CH2I2 (d.34) C2H5I
Q.35 In preparation of CHCl3 from ethanol and bleaching powder, the latter
Provides.....
(a.35) Ca(OH)2 (b.35) Cl2
(c.35) Both (a) and (b) (d.35) All of these
Q.36 Which one of the following processes does not occur during formation
of CHCl3 from C2H5OH and bleaching powder

(a.36) Hydrolysis (b.36) Oxidation
(c.36) Reduction (d.36) Chlorination
Q.37 Which of the following is obtained when chloral is boiled with NaOH
(a.37) CH3Cl (b.37) CHCl3
(c.37) CCl4 (d.37) CH4
Q.38 Chloroform can be obtained from.....
(a.38) Methanol (b.38) Methanal
(c.38) Propanol-1 (d.38) Propanol-2
Q.39 Chlorine reacts with ethanol to give..
(a.39) Ethyl chloride (b.39) Chloroform
(c.39) Acetaldehyde (d.39) Chloral
Q.40 On heating diethyl ether with conc. HI, 2 moles of which of the
following is formed....
(a.40) Ethanol (b.40) None of these
(c.40) Ethyl iodide (d.40) Methyl iodide
Q.41 Lucas reagent is
(a.41) Concentrated HCl + anhydrous ZnCl2
(b.41) Dilute HCl + hydrated ZnCl2
(c.41) Concentrated HNO3 + anhydrous ZnCl2
(d.41) Concentrated HCl + anhydrous MgCl2
Q.42 Which compound does not form iodoform with alkali and iodine
(a.42) Acetone (b.42) Chloroform
(c.42) Diethyl ketone (d.42) Isopropyl alcohol
Q.43 Which compound gives yellow ppt. with iodine and alkali
(a.43) 2-hydroxy propane (b.43) Acetophenone
(c.43) Methyl acetone (d.43) Acetamide
Q.44 Acetone reacts with I2 in presence of NaOH to form
(a.44) C2H5I (b.44) C2H4I2 (c.44) CHI3 (d.44) CH3I
Q.45 Ethanol is converted into ethyl chloride by reacting with
(a.45) Cl2 (b.45) SOCl2 (c.45) HCl (d.45) NaCl
Q.46 C6H5Cl prepared by aniline with
(a.46) HCl
(b.46) Cu2Cl2
(c.46) Cl2 in presence of anhydrous AlCl3
(d.46) HNO2 and then heated with Cu2Cl2
Q.47 The starting substance for the preparation of CH3I is
(a.47) CH3OH (b.47) C2H5OH

(c.47) None of these (d.47) (CH3)2CO
Q.48 A Grignard's reagent may be made by reacting magnesium with....
(a.48) Methyl amine (b.48) Diethyl ether
(c.48) Ethyl iodide (d.48) Ethyl alcohol
Q.49 Which of the following is responsible for iodoform reaction.
(a.49) Formalin (b.49) Methanol
(c.49) None of these (d.49) Ethanol
Q.50 When a solution of sodium chloride containing ethyl alcohol is
electrolysed, it forms......

Answer Key

#27#CH2=CH2+BR2
3
CH OH

2 2 2 2 3
| |
CH CH Br CH CH O CH
Br Br
+
#28# C3H8 + Cl2
Light
C3H7Cl + HCl
This is an example of substitution reaction. Hydrogen atom of alkane
is replaced by halogen atom.
#29# CH CH + HCl CH2=CHCl
HCl +
CH3CHCl2
#30# R-OX+HX R-X+H2O
Reactivity order of alcohols for this reaction
3 > 2 >1


Reactivity order of halogen acids
R-I > R-Br > R-Cl
#31#
U.Vlight
6 6 2 6 6 6
Benzene BHC
C H 3Cl C H Cl +

#32#
#34#
2 3
KI
2 5 3
Na CO
C H OH CHI
#35#
2 2 2 2
Bleachingpowder
CaOCl H O Ca(OH) Cl + +
#36#
Hydrolysis
2 2 2 2
CaOCl H O Ca(OH) Cl + +

Oxidation
3 2 2 3
CH CH OH Cl CH CHO 2HCl + +

Chlorination
3 2 3
CH CHO 3Cl CCl CHO 3HCl + +





#37#
Boil
3 3
Chlorol Chloroform
CCl CHO NaOH CHCl HCOONa + +
#38# CaOCl2 + H2O Ca(OH)2 +Cl2

3 3 2
|
2-propanol
CH CH CH Cl
OH
+
3 3
||
CH C CH 2HCl
O
+

3 3 2 3 3
||
CH C CH 3Cl CCl CO CH 3HCl
O
+ +



#39# CH3CH2OH+Cl2 CH3CHO+2HCl

3 2 3
Chloral
CH CHO 3Cl CCl CHO 3HCl + +
#40#
2 5 2 5 2 5 2
Ethyliodide
C H O C H 2HI 2C H I H O + +
#42#
2
NaOH/ I
3 2 2 3
CH CH CO CH CH No yellow ppt

2
NaOH/ I
3 3 3
CH COCH CHI

2
NaOH/ I
2 5 3
C H OH CHI

2
NaOH/I
3 3 3
|
CH CH CH CHI
OH

#43#
2
NaOH
3 6 5 3
|| I
Yellow ppt.
Acetophenone
COONa
CH CC H CHI
O
+
#44# CH3COCH3 + 3I2 +4NaOH
CHI3+3Na+CH3COONa+3H2O
#45#
Pyridine
2 5 2 2 5 2
C H OH SOCl C H Cl SO HCl + + +

#46#
#47#
2
ZnCl
3 3 2
CH OH HI CH I H O + +
yellow ppt.


#48#
Dry ether
2 5 2 5
Ethyl iodide Ethyl magnesium iodide
C H I Mg C H Mg I +

Testthree
Q.51 Which reagent cannot be used to prepare an alkyl halide from an
alcohol
(a.51) HCl + ZnCl2 (b.51) NaCl
(c.51) PCl5 (d.51) All of these
Q.52 Ethyl benzoate reacts with PCl5 to give
(a.52) C2H5Cl + C6H5COCl+POCl3+HCl
(b.52) C2H5Cl + C6H5COCl + POCl3
(c.52) CH3COCl + C6H5COCl + POCl3
(d.52) C2H5Cl + C6H5COCH + POCl3
Q.53 On treatment with chlorine in presence of sunlight, toluene gives the
product
(a.53) o-chloro toluene (b.53) 2, 5-dichloro toluene
(c.53) p-chloro toluene (d.53) Benzyl chloride
Q.54 When chlorine is passed through warm benzene in presence of the
sunlight, the product obtained is
(a.54) Benzotrichloride (b.54) Chlorobenzene
(c.54) Gammexane (d.54) DDT
Q.55 Which of the following acids adds to propene in the presence of
peroxide to give anti-Markownikoffs product
(a.55) HF (b.55) HCl (c.55) HBr (d.55) H2SO4
Q.56 Propene on treatment with HBr gives..........
(a.56) Isopropyl bromide (b.56) Propyl bromide
(c.56) 1, 2-dibromoethane (d.56) None of the above
Q.57 The catalyst used in Raschig's process is...
(a.57) LiAlH4 (b.57) Copper chloride
(c.57) Sunlight (d.57) Ethanol/ Na
Q.58 The compound formed on heating chlorobenzene with chloral in the
presence of concentrated sulphuric acid, is........
(a.58) Freon (b.58) DDT
(c.58) Gammexene (d.58) Neon
Q.59 Acetone is mixed with bleaching powder to give
(a.59) Chloroform (b.59) Acetaldehyde
(c.59) Ethanol (d.59) Acetone
Q.60 Which of the following compounds gives trichloromethane on distilling

with bleaching powder.........
(a.60) Methanal (b.60) All of these
(c.60) Ethanol (d.60) Methanol
Q.61 The product formed on reaction of ethyl alcohol with bleaching powder is
(a.61) CHCl3 (b.61) CCl3CHO
(c.61) CH3COCH3 (d.61) CH3CHO
Q.62 Ethylene reacts with bromine to form
(a.62) Chloroethane (b.62) Ethylene dibromide
(c.62) Cyclohexane (d.62) 1-bromo propane
Q.63 Best method of preparing alkyl chloride is
(a.63) ROH + SOCl2

(b.63) ROH + PCl5

(c.63) ROH + PCl3

(d.63) ROH + HCl
2
anhy. ZnCl

Q.64 DDT is prepared by reacting chlorobenzene with
(a.64) CCl4 (b.64) CCl3 - CHO
(c.64) CHCl3 (d.64) Propane
Q.65 Which compound needs chloral in its synthesis
(a.65) D. D. T. (b.65) Gammexane
(c.65) Chloroform (d.65) Michlers Ketone
Q.66 To get DDT, chlorobenzene has to react with which of the following
compounds in the presence of concentrated sulphuric acid
(a.66) Trichloroethane (b.66) Dichloroacetone
(c.66) Dichloroacetaldehyde (d.66) Trichloroacetaldehyde
Q.67 What will be the product in the following reaction

(a.67)

(b.67)



(c.67)

(d.67)
Q.68 Compounds A is .......
(a.68) (b.68)
(c.68) (d.68)

Q.69 Ethyl bromide can be converted into ethyl alcohol by
(a.69) Heating with dilute hydrochloric acid and zinc
(b.69) Boiling with an alcoholic solution of KOH
(c.69) The action of moist silver oxide
(d.69) Refluxing methanol
Q.70. Reaction of ethyl chloride with sodium leads to
(a.70) Ethane (b.70) Butane
(c.70) n-butane (d.70) n-pentane
Q.71 Treatment of ammonia with excess of ethyl chloride will yield
(a.71) Diethyl amine
(b.71) Ethane
(c.71) Tetraethyl ammonium chloride
(d.71) Methyl amine
Q.72 2CHCl3 + O2
X
2COCl2 + 2HCl
In the above reaction, X stands for......
(a.72) An oxidant (b.72) A reductant
(c.72) Light and air (d.72) None of these
Q.73 Phosgene is the common name for
(a.73) CO2 and PH3 (b.73) Phosphoryl chloride
(c.73) Carbonyl chloride (d.73) Carbon tetrachloride

Q.74 When chloroform is treated with amine and KOH, we get......
(a.74) Rose odour smell
(b.74) Sour almond like smell
(c.74) Offensive odour
(d.74) Sour oil of winter green like smell
Q.75 A mixture of two organic chlorine compounds was treated with sodium
metal in ether solution. Isobutane was obtained as a product. The two
chlorine compounds are....
(a.75) Methyl chloride and propyl chloride
(b.75) Methyl chloride and ethyl chloride
(c.75) Isopropyl chloride and methyl chloride
(d.75) Isopropyl chloride and ethyl chloride

Answer Key

#56#
3 2 3 3 Marko wnikoff's
|
rule
CH CH CH HBr CH CH CH
Br
= +

#58# DDT is prepared by heating chlorobenzene and chloral with
concentrated sulphuric acid



#59# Acetone forms chloroform when heated with bleaching powder.
CaOCl2+H2O Ca(OH)2+Cl2
CH3COCH3+3Cl2 CCl3COCH3+3HCl

3 3 2 3 3 2
chloroform
2CCl COCH Ca(OH) 2CHCl (CH COO) Ca + +
#60#
2 2 2 2
Bleaching powder
CaOCl H O Ca(OH) Cl + +
Cl2+H2O 2HCl+O


2 5 3 2
ethanol Acetaldehyde
C H OH O CH CHO H O + +

3 2 3
chloral
CH CHO 3Cl CCl CHO 3HCl + +

3 2 3 2
chloroform or
trichloromethane
2CCl CHO Ca(OH) 2CHCl (HCOO) Ca + +
#61# CaOCl2+H2O Ca(OH)2+Cl2
CH3CH2OH+Cl2 CH3CHO+HCl

2
Ca(OH)
3 2 3 3 2
CH CHO Cl CHCl (CH COO) Ca + +
#62# When ethylene reacts with bromine, it forms ethylene dibromide.

2 2 2 2 2
| |
Ethylene Bromine
Ethylene dibromide
H C CH Br H C CH
Br Br
= +
#63# The chlorination of alcohol by SOCl2 (thionyl chloride) is the best
method for the preparation of alkyl halides as in this method all the
other product are gaseous and thus halides are obtained on quite
pure state
2 2
R OH SOCl R Cl HCl SO
A
+ + | + |
#64#
#65# DDT is formed by reaction of chloral with chloro benzene.
#67# NBS is a selective brominating reagent since it normally brominates
the ethylenic compounds in the allylic position.

Properties of Halogen containing compounds
#68#
As CCl3 is a m-directing group.
#69# Ag2O+H2O 2AgOH
C2H5Br+AgOH C2H5OH+AgBr
#70#
Dry
2 5 2 5 2 5 2 5
Ether
C H Cl 2Na ClC H C H C H 2NaCl + + +
#71#
3 2 5
NH C H Cl
2 5 2 5 2 2 5 2
C H Cl C H NH (C H ) NH


2 5 2 5
|
C H Cl C H Cl
2 5 3 2 5 2 5
|
Tetraethyl ammoniumchloride
C H
2 5
(C H ) N C H N C H Cl
C H
2 5
+

(
(
(

(
(
(


If NH3 is in excess, then 1 amine will be the main product, if C2H5Cl
is in excess then mixture of 1,2,3 and quaternary amine is
obtained.
#72#
Light
3 2 2
air
Phosgene
2CHCl O 2COCl 2HCl + +
#73# COCl2 carbonyl chloride is commonly called as phosgene.
#74# C2H5NH2 + CHCl3+3KOH

2 5 2
Ethylisocyanide(offensive odour)
C H N C 3KCl 3H O = + +
#75#
Dry
3 3
Ether
Methyl chloride
|
3
Isopropyl chloride
CH CH Cl 2Na Cl CH
CH
+ +


Testfour
Q.76 Alkyl halides can be converted into Grignard reagents by
(a.76) Boiling them with Mg ribbon in alcoholic solution
(b.76) Warming them with magnesium powder in dry ether
(c.76) Refluxing them with MgCl2 solution
(d.76) Warming them with MgCl2
Q.77 Which is not present in Grignard reagent.......
(a.77) Methyl group (b.77) Magnesium
(c.77) All of these (d.77) COOH group
Q.78 The reactivity of ethyl chloride is.......
(a.78) More or less equal to that of benzyl chloride
(b.78) More than that of benzyl chloride
(c.78) More or less equal to that of chlorobenzene
(d.78) Less than that of chlorobenzene
Q.79 The reactivity of halogen atom is minimum in...
(a.79) Propyl chloride (b.79) None of these
(c.79) Isopropyl chloride (d.79) Isopropyl bromide
Q.80 Chlorobenzene is
(a.80) Less reactive than benzyl chloride
(b.80) More reactive than ethyl bromide

(c.80) Nearly as reactive as methyl chloride
(d.80) More reactive than isopropyl chloride
Q.81 The reactivities of methyl chloride, propyl chloride and chlorobenzene
are in the order
(a.81) Methyl chloride > propyl chloride > chlorobenzene
(b.81) Propyl chloride > methyl chloride > chlorobenzene
(c.81) Methyl chloride > chlorobenzene > propyl chloride
(d.81) Chlorobenzene > propyl chloride > methyl chloride
Q.82 Which of the following compound will make precipitate most readily
with AgNO3
(a.82) CCl3CHO (b.82) CCl4
(c.82) C6H5CH2Cl (d.82) CHI3
Q.83 Carbylamine is liberated when..... is heated with chloroform and
alcoholic potash
(a.83) An aldehyde (b.83) A primary amine
(c.83) A secondary amine (d.83) A phenol
Q.84 Salicylic acid can be prepared using Reimer-Tiemann's reaction by
treating phenol with
(a.84) Methyl chloride in the presence of anhydrous aluminium
chloride
(b.84) Carbon dioxide under pressure in sodium hydroxide solution
(c.84) Carbon tetrachloride and concentrated sodium hydroxide
(d.84) Sodium nitrite and a few drops of concentrated sulphuric acid
Q.85 Grignard reagent is prepared by the reaction between
(a.85) Zinc and alkyl halide
(b.85) Magnesium and alkyl halide
(c.85) Magnesium and alkane
(d.85) Magnesium and aromatic hydrocarbon
Q.86 Reaction of t-butyl bromide with sodium methoxide produces
(a.86) Isobutane (b.86) Isobutylene
(c.86) Sodium t-butoxide (d.86) t-butyl methyl ether
Q.87 War gas is formed from.......
(a.87) PH3 (b.87) C2H2
(c.87) Zinc phosphate (d.87) Chloropicrin
Q.88 What happens when CCl4 is treated with AgNO3
(a.88) NO2 will be evolved
(b.88) A white ppt. Of AgCl will be formed

(c.88) CCl4 will dissolve in AgNO3
(d.88) Nothing will happen
Q.89 If we use pyrene (CCl4) in the Riemer-Tiemann reaction in place of
chloroform, the product formed is....

(a.89) Salicylaldehyde (b.89) Phenolphthalein
(c.89) Salicylic acid (d.89) Cyclohexanol
Q.90 C6H5CH2Cl + KCN(aq.) X + Y


Compounds X and Y are
(a.90) C6H6 + KCl (b.90) C6H5CH2CN + KCl
(c.90) C6H5CH3 + KCl (d.90) None of these
Q.91 The bad smelling substance formed by the action of alcoholic caustic
potash on chloroform and aniline is......
(a.91) Phenyl isocyanide (b.91) Nitrobenzene
(c.91) Phenyl cyanide (d.91) Phenyl isocyanate
Q.92 Ethylidene chloride on treatment with aqueous KOH gives
(a.92) Ethylene glycol (b.92) Acetaldehyde
(c.92) Formaldehyde (d.92) None
Q.93 Reaction C2H5I + C5H11I + 2Na C2H5 C5H11 +2Nal

is called
(a.93) Hoffmann's reaction
(b.93) Dow's reaction
(c.93) Wurtz's reaction
(d.93) Riemer-Tiemann's reaction
Q.94 In presence of AlCl3, benzene and n-propyl bromide react in Friedal-
Craft's reaction to form
(a.94) n-propyl benzene
(b.94) 1, 2-dinormal propyl benzene
(c.94) 1, 4-dinormal propyl benzene
(d.94) Isopropyl benzene
Q.95 The dehydrobromination of 2-bromobutane gives
CH3CH = CHCH3. The product is......
(a.95) Hofmann product
(b.95) Saytzeff product
(c.95) Hoffmann-Saytzeff product
(d.95) Markownikoff product
Q.96 Ethylene difluoride on hydrolysis gives
(a.96) Glycol (b.96) Fluoroethanol
(c.96) Difluoroethanol (d.96) Freon

Q.97 Benzyl chloride when oxidised by pb(NO3)2 gives
(a.97) Benzoic acid (b.97) Benzaldehyde
(c.97) Benzene (d.97) None
Q.98 Which of the following statements about chloroform is false
(a.98) It is a colourless, sweet-smelling liquid
(b.98) It is almost insoluble in water
(c.98) It is highly inflammable
(d.98) It can be used as an inhalational anaesthetic agent
Q.99 CCl4 cannot give precipitate with AgNO3 due to
(a.99) Formation of complex with AgNO3
(b.99) Evolution of Cl2 gas
(c.99) Chloride ion is not formed
(d.99) AgNO3 does not give silver ion
Q.100 On heating CHCl3 with aq. NaOH, the product is......
(a.100) CH3COONa (b.100) HCOONa
(c.100) Sodium oxalate (d.100) CH3OH

Answer Key
#76#
Dry ether
RX Mg R Mg X +
#78#
2 5 6 5 2
more reactive less reactive
C H Cl C H CH Cl >
#80# Chlorobenzene is less reactive than benzyl



chloride

In chlorobenzene the lone pairs present on Cl atom get involved in
resonance with electrons of benzene due to which C-Cl bond acquires
double bond character Hence, reactivity decreases.


#81# CH3-Cl> CH3-CH2-Cl>

#82# CHI3

gives a yellow ppt. of AgI.

#84# O H NaCl NaOH CCl
2 4
2 4 4 + + +

#85#
Dry
ether
Grignard's reagent
RX Mg R Mg X +
(X=Cl,Br,I)

#86#
3
|
Elimination
3 3
|
3
CH
CH C Br CH ONa
CH
+

3
|
3 2 3
Isobutylene
CH
CH C CH CH OH NaBr = + +
CH3ONa CH3O
-
+Na
+

methoxide ion (CH3O
-
) is a strong base, therefore it abstract proton
from 3 alkyl halide and favours elimination reaction.
#87#
3 2 3 2 2
Chloropicrin (war gas)
CHCl HO NO CCl NO H O + +
#88# CCl4 +AgNO3 No reaction
CCl4 is a covalent compound. Therefore does not provide Cl
-
ions.
#89#



#90# C6H5 - CH2 Cl + KCN(aq) C6H5 - CH2 C N + KCl
#91#

#92#
#94#



#95#

#96#
2 2
Hydrolysis
| |
2 2
CH F CH OH
CH F CH OH

#97#
#99# CCl4 is a covalent compound, Hence it does not give Cl
-
ion in
solution.
CCl4 + AgNO3No reaction

#100#


Testfive
Q.101 Ethyl bromide reacts with lead-sodium alloy to form
(a.101) Tetraethyl lead (b.101) Tetraethyl bromide
(c.101) Both (a) and (b) (d.101) None of the above
Q.102 Iodoform heated with Ag powder to form
(a.102) Acetylene (b.102) Ethylene
(c.102) Methane (d.102) Ethane
Q.103 Ethyl bromide reacts with silver nitrite to form
(a.103) Nitroethane
(b.103) Nitroethane and ethyl nitrite
(c.103) Ethyl nitrite
(d.103) Ethane
Q.104 Which of the following reactions leads to the formation of chloritone
(a.104) CHCl3 + CH3COCH3 (b.104) CCl4 + Acetone
(c.104) CHCl3 + KOH (d.104) CHCl3 + HNO3
Q.105 CH3 CH2 - CH2Br + KOH (alc.) Product. Product in above reaction
is...... (a.105) CH3 CH = CH2 (b.105) CH3 CH2 CH3
(c.105) (a) and (b) both (d.105) None of these
Q.106 A + CCl4 + KOH Salicylic acid
A in above reaction is......
(a.106) (b.106)
(c.106) (d.106)
Q.107 Identify X and Y in the following sequence
C2H5Br
X
product
Y
C3H7NH2


(a.107) X = KCN, Y = LiAlH4
(b.107) X = KCN, Y = H3O
+

(c.107) X = CH3Cl, Y = AlCl3 / HCl
(d.107) X = CH3NH2, Y = HNO2
Q.108 1-chlorobutane reacts with alcoholic KOH to form
(a.108) 1-butene (b.108) 2-butane
(c.108) 1-butanol (d.108) 2-butanol
Q.109 Which of the following reactions gives H2C = C = C = CH2

(a.109) CH2Br-CBr= CH2
3
Zn/Ch OH

(b.109) HC C CH2 -COOH
2 3
o
Aq.K CO
40 C

(c.109) CH2Br C C- CH2Br
Zn
Heat

(d.109) 2CH2 = CH CH2I
Q.110 When ethyl amine is heated with chloroform and alcoholic KOH, a
compound with offensive smell is obtained. This compound is......
(a.110) A secondary amine (b.110) An isocyanide
(c.110) A cyanide (d.110) An acid
Q.111 Chlorobenzene on fusing with solid NaOH gives
(a.111) Benzene (b.111) Benzoic acid
(c.111) Phenol (d.111) Benzene chloride
Q.112 DDT can be prepared by reacting chlorobenzene (in the presence of
conc.H2SO4) with
(a.112) Cl2 in ultraviolet light (b.112) Chloroform
(c.112) Trichloroacetone (d.112) Chloral hydrate
Q.113 When phenol reacts with CHCl3 and KOH, the product obtained would
be
(a.113) Salicylaldehyde (b.113) p-hydroxy benzaldehyde
(c.113) Both (a) and (b) (d.113) Chloretone
Q.114 Ethyl chloride on heating with silver cyanide forms a compound X.
The functional isomer of X is......
(a.114) C2H5NC (b.114) C2H5CN
(c.114) H3C NH CH3 (d.114) C2H5NH2
Q.115 Which of the following statements is incorrect
(a.115) C2H5Br reacts with alco. KOH to form C2H5OH
(b.115) C2H5Br when treated with metallic sodium gives ethane
(c.115) C2H5Br when treated with sodium ethoxide forms diethyl ether
(d.115) Both (a) and (b)
Q.116 When chloroform is exposed to air and sunlight, it gives
(a.116) Carbon tetrachloride (b.116) Carbonyl chloride
(c.116) Mustard gas (d.116) Lewsite
Q.117 An organic halide is shaken with aqueous NaOH followed by the
addition of dil. HNO3 and silver nitrate solution gave white ppt. The
substance can be
(a.117) C6H4(CH3)Br (b.117) C6H5CH2Cl
(c.117) C6H5Cl (d.117) None of these
Q.118 A compound A has a molecular formula C2Cl3OH. It reduces Fehling

solution and on oxidation gives a monocarboxylic acid (B). A is
obtained by action of chlorine on ethyl alcohol. A is......
(a.118) Chloral (b.118) CHCl3
(c.118) CH3Cl (d.118) Chloroacetic acid
Q.119 Following equation illustrates
C6H5Cl + 2NaOH
o
200 250 C
200atm

C6H5ONa + NaCl + H2O

(a.119) Dow's process (b.119) Kolbe's process
(c.119) Carbylamine test (d.119) Haloform reaction
Q.120 One of the following that cannot undergo dehydro-halogenation
is...... (a.120) Iso-propyl bromide (b.120) Ethanol
(c.120) Ethyl bromide (d.120) None of these
Q.121 A compound X on reaction with chloroform and NaOH gives a
compound with a very unpleasant odour. X is......
(a.121) C6H5CONH2 (b.121) C6H5NH2
(c.121) C6H5CH2NHCH3 (d.121) C6H5NHCH3

Q.122
In the above reaction product is......
(a.122) C6H5OC2H5 (b.122) C2H5OC2H5
(c.122) C6H5OC6H5 (d.122) C6H5I
Q.123 C2H5Cl + KCN X
Hydrolysis
Y. 'X' and 'Y' are
(a.123) C2H6 and C2H5CN
(b.123) C2H5CN and C2H6
(c.123) C2H5CN and C2H5CH2NH2


(d.123) C2H5CN and C2H5COOH


Q.124 Iodoform is formed on warming I2 and NaOH with
(a.124) C2H5OH (b.124) CH3OH
(c.124) HCOOH (d.124) C6H6
Q.125 Which of the following reacts with phenol to give salicylaldehyde after
hydrolysis
(a.125) Dichloromethane (b.125) Trichloromethane
(c.125) Methyl chloride (d.125) None of these

Answer Key


#101#
2 5 2 5 4
Tetra Ethyl lead
(TEL)
4C H Br 4Pb / Na (C H ) Pb 4NaBr + +
#102#
3 3
Acetylene
CHI 6Ag I CH CH CH 6AgI + + +

#103#

Ag-O-N=O is a covalent compound. Therefore, attack of
nucleophile occurs through Nitrogen atom. Hence, nitroethane is
formed.
#107# C2H5Br
KCN(X)
C2H5CN
4
LiAlH (Y)
C2H5CH2NH2(C3H7NH2)
X=KCN,Y=LiAlH4

#108# CH3CH2CH2CH2 Cl + KOH(alc.)
3 2 2 2
1-butene
CH CH CH CH KCl H O = + +
#109#
Zn
2 2
CH Br C C CH Br
A
CH2=C=C=CH2
#110#
2 5 2 3 2 5
ethyl amine Reaction Ethylisocyanide
(Unpleasant smell)
C H NH CHCl 3KOH C H N C + + =
+3KCl + 3H2O


#111#

#113#
#114#
2 5 2 5
Ethyl isocyanide
(X)
C H Cl AgCN C H N C AgCl + = +
The functional isomer of ethyl isocyanide is ethyl cyanide C2H5-CN.

#115# C2H5Br+alc.KOH C2H4+H2O+KBr

#116#
Sunlight
3 2 2
Phosgene or carbonyl chloride
1
CHCl O COCl HCl
2
+ +

#117#
NaOH
6 5 2 6 5 2
(aq)
C H CH Cl C H CH OH
3
dil HNO
6 5
C H CHO
White ppt of AgCl are obtained.
#118#
2 3 2
A
C Cl OH Fehlingsol. Cu O
Red ppt
+
It means CHO group is present.

Oxidation
2 3 3
A Monocarboxylic acid
C Cl OH CCl COOH
It means only one CHO group is present.
C2H5OH+Cl2CH3CHO+2HCl

3 2 3
Chloral
CH CHO 3Cl CCl CHO 3HCl + +
#120# Ethanol cannot undergo dehydrohalogenation.
#121#
6 5 2 3
(Aniline)
X
C H NH CHCl 3NaOH + +
2 6 5
Phenyl isocyanide
3NaCl 3H O C H N C + + =
#122#




#123# C2H5Cl+KCN
Hydrolysis
2 5 2 5
Ethyl cyanide Propanoic acid
(X) (Y)
C H CN C H COOH
#124#
2
NaOH
2 5 3
I
C H OH CHI
#125#


Testsix
Q.126 Dehydrohalogenation in monohaloalkanes produces
(a.126) A single bond (b.126) A double bond
(c.126) A triple bond (d.126) Fragmentation
Q.127 When chloroform is treated with conc. HNO3 it gives
(a.127) CHCl2NO2 (b.127) CCl3NO2
(c.127) CHCl2HNO3 (d.127) None of these
Q.128 A sample of chloroform being used as anaesthetic is tested by

(a.128) Fehling solution
(b.128) AgNO3

solution
(c.128) AgNO3

solution after boiling with alcoholic KOH solution
(d.128) Both (b) and (c)
Q.129 Dehydrohalogenation of an alkyl halide is......
(a.129) An addition reaction (b.129) A substitution reaction
(c.129) An elimination reaction (d.129) An oxidation reaction
Q.130 Reaction of aqueous sodium hydroxide on (i) ethyl bromide and (ii)
chlorobenzene gives
(a.130) (i) Ethene and (ii) o-chlorophenol
(b.130) (i) Ethyl alcohol and (ii) o-chlorophenol
(c.130) (i) Ethyl alcohol and (ii) phenol
(d.130) (i) Ethyl alcohol and (ii) no reaction
Q.131 2-bromopentane is heated with potassium ethoxide in ethanol. The
major product obtained is
(a.131) Pentene-1 (b.131) cis pentene-2
(c.131) trans pentene-2 (d.131) 2-ethoxypentane
Q.132 What is the product formed in the following reaction
C6H5OH + CCl4
(1) NaOH
(2) H
+

(a.132) p-hydroxybenzoic acid (b.132) o-hydroxybenzoic acid
(c.132) Benzaldehyde (d.132) Salicylaldehyde
Q.133 When chloroform is treated with excess oxygen it forms
(a.133) COCl2 + HCl
(b.133) COCl2 + Cl2 + H2
(c.133) COCl2 + Cl2 +H2O
(d.133) No product will be formed
Q.134 Which isomer of cyclohexane hexachloride is a very strong insecticide
(a.134) (b.134)
(c.134) (d.134) X
Q.135 Haloalkane in the presence of alcoholic KOH undergoes
(a.135) Elimination (b.135) Polymerisation
(c.135) Dimerisation (d.135) Substitution
Q.136 The set of compounds in which the reactivity of halogen atom in the
ascending order is......
(a.136) Vinyl chloride, chlorethane, chlorobenzene
(b.136) Vinyl chloride, chlorobenzene, chloroethane
(c.136) Chloroethane, chlorobenzene, vinyl chloride

(d.136) Chlorobenzene, vinyl chloride chloroethane
Q.137 Alkyl halides react with Mg in dry ether to form
(a.137) Magnesium halide (b.137) Grignards reagent
(c.137) Alkene (d.137) Alkyne
Q.138 In the following sequence of reactions

KOH(alc) HBr KOH(aq.)
3 2 2
CH CH CH Br (A) (B) (C), The product (C) is......
(a.138) Propan 2 - ol (b.138) Propan l ol
(c.138) Propyne (d.138) Propene
Q.139 Alkyl halide on heating with alc. NH3 in a sealed tube results
(a.139) 1 amine (b.139) 2 amine
(c.139) 3 amine (d.139) All of these
Q.140 When CH3CH2CHCl2 is treated with NaNH2, the product formed is......
(a.140) CH3-CH = CH2 (b.140) CH3 - C CH
(c.140) CH3CH2CH(NH2)(Cl) (d.140) CH3CH2C (NH2)2
Q.141 By heating a mixture of CHCl3 with silver powder, the compound
formed is......
(a.141) Acetylene (b.141) Silver acetate
(c.141) Propanol (d.141) None of these
Q.142 Chloropicrin is......
(a.142) Trichloro acetaldehyde (b.142) Nitrochloroform
(c.142) 2,4,6-trinitro phenol (d.142) None of these
Q.143 Which of the following are correct statements about C2H5Br
(a.143) It reacts with metallic Na to give ethane
(b.143) It gives nitroethane on heating with aqueous ethanolic
solution of AgNO2
(c.143) It forms ethylacetate on heating with silver acetate
(d.143) Both (b) and (c)
Q.144 Aryl halide is less reactive than alkyl halide towards nucleophilic
substitution because
(a.144) Less stable carbonium ion
(b.144) Due to large C Cl

bond energy
(c.144) Inductive effect
(d.144) Resonance stabilization and sp
2
- hybridisation of C attached
to halide
Q.145 Methyl chloride reacts with silver acetate to yield
(a.145) Acetaldehyde (b.145) Acetyl chloride
(c.145) Methyl acetate (d.145) Acetic acid

Q.146 Chloroform for anesthetic purposes is tested for its purity with the
reagent
(a.146) Silver nitrate (b.146) Lead nitrate
(c.146) Ammoniacal Cu2Cl2 (d.146) Lead nitrate
Q.147 2, 6 - Dimethylheptane on monochlorination produces.
derivatives
(a.147) 5 (b.147) 6
(c.147) 1 (d.147) 4
Q.148 The less reactivity of chlorine atom in CH2 = CH - Cl is due to
(a.148) Inductive effect (b.148) Resonance stabilization
(c.148) Electromeric effect (d.148) All of these
Q.149
CH3-CH2-Br
alc.KCN
CH3CH2CN
HOH

X
In this reaction, product X is......
(a.149) Acetic acid (b.149) Propionic acid
(c.149) Butyric acid (d.149) Hydrochloric acid
Q.150 In alkaline hydrolysis of a tertiary alkyl halide by aqueous alkali if
concentration of alkali is doubled, then the reaction
(a.150) Will be doubled (b.150) Will be halved
(c.150) Will remain constant (d.150) Cant say

Answer Key

#126#
#127#
3 3 3 2 2
Chloroform Chloropicrin
CHCl conc. HNO CCl NO H O + +
#128# Before using the sample of chloroform as an anaesthetic, it is tested
by treating with aq. solution of AgNO3. A pure sample does not give
ppt with aq. AgNO3.
#129# Alkyl halide gives alkene on elimination, reaction takes place in
presence of alc. KOH.
CH3CH2Br+Alc.KOHCH2=CH2+KBr+H2O
There are two types of elimination reactions.
(a) E1 Unimolecular elimination
(b) E2 Bimolecular elimination
#130# (i) Ethyl alcohol (ii) Phenol


2 5 2 5
(aq)
Ethyl alcohol
C H Br NaOH C H OH NaBr + +


#131#
3 2 2 3
|
CH CH CH CH CH KOH
Br
+
2 5
C H OH
3 2 3
Elimination
2-Pentene
reaction
CH CH CH CH CH =
When alkyl halide reacts with alc. KOH then it favours elimination
reaction (Dehydrohalogenation). Since, trans pentene-2 is more
symmetrical than cis isomers. Hence, it is main product.

#133#
hv
3 2 2 2 2
CHCl O COCl Cl H O + + +
#137# Alkyl halide reacts with Mg in presence of dry ether to give alkyl
magnesium halide which is also called as Grignard reagent. This
reaction is also called as Grignards reaction.

dry
ether
Grignard's reagent
R X Mg R Mg X +
#138#
alc. KOH
3 2 2 3 2
CH CH CH Br CH CH CH
(A)
=

aq.KOH
3 3 3 3
| |
Propan-2-ol
CH CH CH CH CH CH
Br OH


#143#
2 5 2 2 5 2
nitro ethane
C H Br alc. AgNO C H NO AgBr + +

2 5 3 3 2 5
Ester
C H Br CH COOAg CH COO C H AgBr + +
#146# If CHCl3 sample contains phosgene (COCl2) then it will give a white ppt.
When treated with cold AgNO3.
HBr

#147# Because
3 2 2 2 3
| |
3 3
CH CH CH CH CH CH CH
CH CH
has four methyl
groups on the corner so it can produce for derivatives

Testseven
Q.151 AgNO3 does not give precipitate with CHCl3 because
(a.151) CHCl3 does not ionise in water
(b.151) AgNO3 does not reacts with CHCl3
(c.151) CHCl3 is chemically inert
(d.151) None of these
Q.152 The reaction between chlorobenzene and chloral in the presence of
concentrated sulphuric acid produces
(a.152) Gammexane
(b.152) p,p-dichloro diphenyl trichloro ethane
(c.152) Chloropicrin
(d.152) Benzene hexachloride
Q.153 False statement is......
(a.153) Vinyl chloride is more reactive than allyl chloride
(b.153) Br
-

is a good nucleophile as compared to I
-

(c.153) Chloroform is heavier than water
(d.153) Both (a) and (b)
Q.154 Chloroform is slowly oxidise by air in presence of light to form
(a.154) Formyl chloride (b.154) Phosgene
(c.154) Trichloroacetic acid (d.154) Formic acid
Q.155 Alcoholic potash is used to bring about
(a.155) Dehydrogenation (b.155) Dehydration
(c.155) Dehydrohalogenation (d.155) Dehalogenation
Q.156 Vinyl chloride reacts with HCl

to form
(a.156) 1, 1- dichloro ethane
(b.156) 1, 2- dichloro ethane
(c.156) Tetrachloro ethylene
(d.156) Mixture of 1, 2 and 1, 1 dichloro ethane
Q.157
R-X + NaOH
ROH + NaX


The above reaction is classified as
(a.157) Nucleophilic substitution
(b.157) Electrophilic substitution
(c.157) Reduction

(d.157) Oxidation
Q.158 Reduction of acetyl chloride with H2 in presence of Pd gives
(a.158) CH3COCH3 (b.158) C2H5OH
(c.158) CH3COOH (d.158) CH3CHO
Q.159 When methyl bromide is heated with Zn it gives
(a.159) CH4 (b.159) C2H6
(c.159) C2H4 (d.159) CH3OH
Q.160 Phenol reacts with CHCl3 and NaOH (at 340 K) to give
(a.160) o-chlorophenol (b.160) Salicylaldehyde
(c.160) Benzaldehyde (d.160) Chlorobenzene
Q.161 Iodoform on heating with KOH gives
(a.161) CH3CHO (b.161) CH3COOK
(c.161) HCOOK (d.161) HCHO
Q.162 Which reaction is correct in the conversion of chloroform to acetylene
(a.162) CHCl3 + AgNO3 (b.162) CHCl3 + O2
(c.162) CHCl3 + HNO3 (d.162) CHCl3 + Ag
Q.163 Which of the following gases are poisonous
(a.163) CHCl3 (b.163) CO2
(c.163) None of these (d.163) CO
Q.164 Which of the following alkyl halide is used as a methylating agent
(a.164) CH3I (b.164) C2H5Br
(c.164) C2H5Cl (d.164) C6H5Cl
Q.165 C6H6Cl6 , on treatment with alcoholic KOH, yields
(a.165) C6H6 (b.165) C6H3Cl3
(c.165) (C6H6)OH (d.165) C6H6Cl4
Q.166 When ethyl iodide is heated with silver nitrate, the product obtained is
(a.166) C2H5Ag (b.166) Ag-O-NO2
(c.166) C2H5O-NO2 (d.166) C2H5I-NO2
Q.167 CHCl3 and HF lead to the formation of a compound of fluorine of
molecular weight 70. The compound is
(a.167) Fluoroform (b.167) Fluorine monoxide
(c.167) Fluorine dioxide (d.167) Fluromethanol
Q.168 Chloroform with zinc dust in water gives
(a.168) CH4 (b.168) Chloropicrin
(c.168) CCl4 (d.168) CH2Cl2
Q.169 Which of the following is used as a catalyst for preparing Grignard
reagent

(a.169) Iron powder (b.169) Iodine powder
(c.169) Activated charcoal (d.169) Manganese dioxide
Q.170 For a given alkyl group the densities of the halides follow the order
(a.170) RI < RBr < RCl (b.170) RI < RCl < RBr
(c.170) RBr < RI < RCl (d.170) RCl < RBr < RI
Q.171 Which halide will be least reactive in respect to hydrolysis
(a.171) Vinyl chloride (b.171) Allyl chloride
(c.171) Ethyl chloride (d.171) t-Butyl chloride
Q.172 In nucleophilic aliphatic substitution, the nucleophiles are generally
(a.172) Acids (b.172) Bases
(c.172) Salts (d.172) Neutral molecules
Q.173 Which one of the following compounds does not react with bromine
(a.173) Ethylamine (b.173) Propene
(c.173) Phenol (d.173) Chloroform
Q.174 Allyl chloride on dehydro chlorination gives
(a.174) Propadiene (b.174) Propylene
(c.174) Acetylchloride (d.174) Acetone
Q.175 Toluene reacts with excess of Cl2 in presence of sunlight to give a
product which on hydrolysis followed by reaction with NaOH gives
(a.175) (b.175)
(c.175) (d.175) None of these


Testeight
Q.176 An alkyl bromide produces a single alkene when it reacts with sodium
ethoxide and ethanol. This alkene undergoes hydrogenation and
produces 2-methyl butane. What is the identity of the alkyl bromide
(a.176) 1-bromo-2, 2-dimethylpropane
(b.176) 1-bromobutane
(c.176) 1-bromo-2-methylbutane
(d.176) 2-bromo-2-methylbutane
(e.176) 2-bromopentane
Q.177 On treating a mixture of two alkyl halides with sodium metal in dry
ether, 2-methyl propane was obtained. The alkyl halides are
(a.177) 2-chloropropane and chloromethane

(b.177) 2-chloropropane and chloroethane
(c.177) Chloromethane and chloroethane
(d.177) Chloromethane and 1-chloropropane
Q.178 In which case formation of butane nitrile is possible
(a.178) C3H7Br + KCN (b.178) C4H9Br + KCN
(c.178) C3H7OH + KCN (d.178) C4H9OH + KCN
Q.179 The reaction of an aeromatic halogen compound with an alkyl halides
in presence of sodium and ether is called
(a.179) Wurtz reaction
(b.179) Sandmeyers reaction
(c.179) Wurtz-fittig reaction
(d.179) Kolbe reaction
Q.180 The compound added to prevent chloroform to form phosgene gas
is......
(a.180) C2H5OH (b.180) CH3COOH
(c.180) CH3COCH3 (d.180) CH3OH
Q.181 Among the following, the one which reacts most readily with ethanol
is......
(a.181) p-nitrobenzyl bromide
(b.181) p-chlorobenzyl bromide
(c.181) p-methoxybenzyl bromide
(d.181) p-methylbenzyl bromide
Q.182 Chloropicrin is obtained by the reaction of
(a.182) Chlorine on picric acid
(b.182) Nitric acid on chloroform
(c.182) Steam on carbon tetrachloride
(d.182) Nitric acid on chlorobenzene
Q.183 In Wurtz reaction alkyl halide react with
(a.183) Sodium in ether (b.183) Sodium in dry ether
(c.183) Sodium only (d.183) Alkyl halide in ether
Q.184 Chloroform, when kept open, is oxidised to
(a.184) CO2 (b.184) COCl2
(c.184) CO2, Cl2 (d.184) None of these
Q.185 Chloroform reacts with concentrated HNO3 to give
(a.185) Water gas (b.185) Tear gas
(c.185) Laughing gas (d.185) Producer gas
Q.186 When ethyl chloride and alcoholic KOH are heated, the compound

obtained is
(a.186) C2H4 (b.186) C2H2
(c.186) C6H6 (d.186) C2H6
Q.187 Chloroform, on warming with Ag powder, gives
(a.187) C2H6 (b.187) C3H8
(c.187) C2H4 (d.187) C2H2
Q.188 When alkyl halide is heated with dry Ag2O, it produces
(a.188) Ester (b.188) Ether
(c.188) Ketone (d.188) Alcohol
Q.189 Reaction of alkyl halides with aromatic compounds in presence of
anhydrous AlCl3 is known as
(a.189) Friedal-Craft reaction
(b.189) Hofmann degradation
(c.189) Kolbes synthesis
(d.189) Beckmann rearrangement
Q.190 Two percent of ethanol is added during the oxidation of chloroform to
stop the formation of carbonyl chloride. In this reaction ethanol acts
as
(a.190) Auto catalyst (b.190) Negative catalyst
(c.190) Positive catalyst (d.190) None of these
Q.191 When benzene is heated with chlorine in the presence of sunlight, it
forms
(a.191) B.H.C. (b.191) Cyclopropane
(c.191) p-dichlorobenzene (d.191) None of these
Q.192 Ethylene di bromide on heating with metallic sodium in ether solution
yields
(a.192) Ethene (b.192) Ethyne
(c.192) 2-butene (d.192) 1-butene
Q.193 The reaction,CH3Br + Na Product, is called
(a.193) Perkin reaction (b.193) Levit reaction
(c.193) Wurtz reaction (d.193) Aldol condensation
Q.194 At normal temperature iodoform is
(a.194) Thick viscous liquid (b.194) Gas
(c.194) Volatile liquid (d.194) Solid
Q.195 Which of the following statements about benzyl chloride is incorrect
(a.195) It is less reactive than alkyl halides

(b.195) It can be oxidised to benzaldehyde by boiling with copper
nitrate solution
(c.195) It is a lachrymatory liquid and answers Beilsteins test
(d.195) It gives a white precipitate with alcoholic silver nitrate
Q.196 Ethylene dichloride and ethylidine chloride are isomeric compounds.
The false statement about these isomers is that they
(a.196) React with alcoholic potash and give the same product
(b.196) Are position isomers
(c.196) Contain the same percentage of chlorine
(d.196) Are both hydrolysed to the same product
Q.197 An alkyl bromide (X) reacts with Na to form 4, 5-diethyloctane.
Compound X is......
(a.197) CH3(CH2)3Br
(b.197) CH3(CH2)5Br
(c.197) CH3(CH2)3CH.Br.CH3
(d.197) CH3(CH2)2CH.Br.CH2CH3
Q.198 In the following reaction X is......
CH3NH2 + X+ KOH CH3NC ( highly offensive odour)
(a.198) CH2Cl2 (b.198) CHCl3
(c.198) CH3Cl (d.198) CCl4
Q.199 Which metal is used in Wurtz synthesis......
(a.199) Ba (b.199) Al
(c.199) Na (d.199) Fe
Q.200 Which of the following is boiled with ethyl chloride to form ethyl
alcohol
(a.200) Alcoholic KOH (b.200) Aqueous KOH
(c.200) H2O (d.200) H2O2

Testnine

Q.201 Why is chloroform put into dark coloured bottles
(a.201) To prevent evaporation
(b.201) To prevent from moisture
(c.201) To prevent it from oxidation to form phosgene
(d.201) To prevent its reaction with glass
Q.202 DDT is......
(a.202) A solid (b.202) A liquid (c.202) A gas (d.202) A solution

Q.203 Bottles containing C6H5I and C6H5CH2I lost their original labels. They
were labelled A and B for testing. A and B were separately taken in test
tubes and boiled with NaOH solution. The end solution in each tube
was made acidic with dilute HNO3 and then some AgNO3 solution was
added. Substance B give a yellow precipitate. Which one of the
following statements is true for this experiment
(a.203) A was C6H5I
(b.203) A was C6H5CH2I
(c.203) B was C6H5I
(d.203) Addition of HNO3was unnecessary
Q.204 Which of the following statements is incorrect regarding benzyl
chloride
(a.204) It gives white precipitate with alcoholic AgNO3
(b.204) It is an aromatic compound with substitution in the side chain
(c.204) It undergoes nucleophilic substitution reaction
(d.204) It is less reactive than vinyl chloride
Q.205 Alkyl halide can be converted into alkene by
(a.205) Nucleophilic substitution reaction
(b.205) Elimination reaction
(c.205) Both nucleophilic substitution and elimination reaction
(d.205) Rearrangement
Q.206 The major product formed in the following reaction is......

3
3
3
|
CH O
3 2
| CH OH
CH
CH C CH Br
H

(a.206)
3
|
3 2 3
|
CH
CH C CH OCH
H


(b.206)
3 2 3
|
3
CH CH CH CH
OCH

(c.206)
3
|
3 2
CH
CH C CH =
(d.206)
3
|
3 3
|
3
CH
CH C CH
OCH

Q.207 The major product obtained on treatment of CH3CH2CH(F)CH3 with
CH3O
-
/ CH3OH is......

(a.207) CH3CH2CH(OCH3)CH3
(b.207) CH3CH=CHCH3
(c.207) CH3CH2CH = CH2
(d.207) CH3CH2CH2CH2OCH3
Q.208 When phenyl magnesium bromide reacts with tbutanol, the product
would be
(a.208) Benzene (b.208) Phenol
(c.208) tbutyl benzene (d.208) tbutyl phenyl ether
Q.209 Alkyl halides react with dialkyl copper reagents to give
(a.209) Alkenes (b.209) Alkyl copper halides
(c.209) Alkanes (d.209) Alkenyl halides
Q.210 Which of the following is liquid at room temperature
(a.210) CH3I (b.210) CH3Br
(c.210) C2H5Cl (d.210) CH3F
Q.211 Which of the following haloalkanes is most reactive
(a.211) 1-chloropropane (b.211) 1-bromopropane
(c.211) 2-chloropropane (d.211) 2-bromopropane
Q.212 Grignard reagent adds to
(a.212) > C = O (b.212) C N
(c.212) > C =S (d.212) All of the above
Q.213 Analyse the following reaction and identify the nature of A and B


(a.213) Both A and B are

(b.213) Both A and B are

(c.213) A is & B is

(d.213) A is & B is
(e.213) A is & B is
Q.214 Which of these can be used as moth repellant
(a.214) Benzene hexachloride (b.214) Benzal chloride
(c.214) Hexachloroethane (d.214) Tetrachloroethane
Q.215 Which one of the following is the correct formula of dichlorodiphenyl
trichloroethane
(a.215)


(b.215)



(c.215)



(d.215)
Q.216 The compound
|
3 2 3
OH
(CH ) .CCCl is......
(a.216) Chloretone (b.216) Chloroquin
(c.216) Chloropicrin (d.216) Chloropropyl chloride
Q.217 Depletion of ozone layer is caused by
(a.217) Freon (b.217) Alkane
(c.217) Gringard reagent (d.217) All of these
Q.218 Which of the following is Teflon
(a.218) [-CF2 CF2-]n (b.218) CF2 = CF2
(c.218) CF CF (d.218) None of these
Q.219 Statement Ozone in atmosphere is decreased by chloro-fluoro-
carbon (Cl2F2C)
(a.219) Is true
(b.219) Is false
(c.219) Only in presence of CO2
(d.219) Only in absence of CO2
Q.220 CFxCly[where x + y = 4]. These compounds are not used because
(a.220) These are fluoro carbons
(b.220) These are difficult to synthesise
(c.220) They deplete ozone layer
(d.220) None of the these
Q.221 The molecular formula of DDT has
(a.221) 5 chlorine atoms (b.221) 4 chlorine atoms
(c.221) 3 chlorine atoms (d.221) 2 chlorine atoms
Q.222 What is the reagent used for testing fluoride ion in water
(a.222) Alizarin - S (b.222) Quinalizarin
(c.222) Phenolphthalein (d.222) Benzene
Q.223 Chloropicrin is used as
(a.223) Solvent (b.223) Anaesthetic
(c.223) Perfume (d.223) Tear gas
Q.224 Which is used in the manufacture of plastic

(a.224) CH2 = CHCl (b.224) CH CH
(c.224) CH2 = CH CH2I (d.224) CCl4
Q.225 Freon (dichlorodifluoro methane) is used
(a.225) As local anaesthetic
(b.225) For dissolving impurities in metallurgical process
(c.225) In refrigerator
(d.225) In printing industry

Testten
Q.226 Which of the following is known as freon which is used as a
Refrigerant
(a.226) CCl2F2 (b.226) CHCl3
(c.226) CH2F2 (d.226) CF4
Q.227 Benzene hexachloride (BHC) is used as
(a.227) Dye (b.227) Antimalerial drug
(c.227) Antibiotic (d.227) Insecticide
Q.228 Which plastic is obtained from CHCl3 as follows

o
3
HF 800 C Polymerisation
3
SbF
CHCl X Y Plastic
(a.228) Bakelite (b.228) Teflon
(c.228) Polythene (d.228) Perspex
Q.229 The above structural formula refers to
(a.229) BHC (b.229) DNA
(c.229) DDT (d.229) RNA
Q.230 The commercial uses of DDT and benzene hexachloride are
(a.230) DDT is a herbicide, benzene hexachloride is a fungicide
(b.230) Both are insecticides
(c.230) Both are herbicides
(d.230) DDT is a fungicide and benzene hexachloride is a herbicide
Q.231 Which of the following is used in fire extinguishers
(a.231) CH4 (b.231) CHCl3
(c.231) CH2Cl2 (d.231) CCl4
Q.232 Iodoform can be used as
(a.232) Anaesthetic (b.232) Antiseptic
(c.232) Analgesic (d.232) Antifebrin

Q.233 Which of the following is an anaesthetic
(a.233) C2H4 (b.233) CHCl3
(c.233) CH3Cl (d.233) C2H5OH
Q.234 An important insecticide is obtained by the action of chloral on
chlorobenzene. It is
(a.234) BHC (b.234) Gammexene
(c.234) DDT (d.234) Lindane
Q.235 In fire extinguisher, pyrene is
(a.235) CO2 (b.235) CCl4
(c.235) CS2 (d.235) CHCl3
Q.236 B.H.C. is used as
(a.236) Insecticide (b.236) Pesticide
(c.236) Herbicide (d.236) Weedicide
Q.237 The use of the product obtained as a result of reaction between
acetone and chloroform is......
(a.237) Hypnotic (b.237) Antiseptic
(c.237) Germicidal (d.237) Anaesthetic
Q.238 Use of chlorofluoro carbons is not encouraged because
(a.238) They are harmful to the eyes of people that use it
(b.238) They damage the refrigerators and air conditioners
(c.238) They eat away the ozone in the atmosphere
(d.238) They destroy the oxygen layer
Q.239 Among the following, the molecule with the highest dipole moment
is...... (a.239) CH3Cl (b.239) CH2Cl2 (c.239) CHCl3 (d.239) CCl4
Q.240 When CHCl3 is boiled with NaOH, It gives
(a.240) Formic acid (b.240) Trihydroxy methane
(c.240) Acetylene (d.240) Sodium formate
Q.241 The hybridization state of carbon atoms in the product formed by the
reaction of ethyl chloride with aqueous potassium hydroxide is......
(a.241) sp (b.241) sp
2
(c.241) sp
3
(d.241) sp
3
d
Q.242 Which of the following compounds does not undergo nucleophilic
substitution reactions
(a.242) Vinyl chloride (b.242) Ethyl bromide
(c.242) Benzyl chloride (d.242) Isopropyl chloride
Q.243 Replacement of Cl of chlorobenzene to give phenol requires drastic
conditions but chlorine of 2, 4-dinitrochlorobenzene is readily
replaced because

(a.243) NO2 make ring electron rich at ortho and para
(b.243) NO2withdraws e
-
from meta position
(c.243) denotes e
-
at meta position
(d.243) NO2 withdraws e
-
from ortho/para positions
Q.244 Among the following one with the highest percentage of chlorine
is...... (a.244) Chloral (b.244) Pyrene
(c.244) PVC (d.244) Gammexene
Q.245 In which alkyl halide,SN
2
mechanism is favoured maximum
(a.245) CH3Cl (b.245) CH3CH2Cl
(c.245) (CH3)2CHCl (d.245) (CH3)3C-Cl
Q.246 Which conformation of C6H6Cl6 is most powerful insecticide
(a.246) aaeeee (b.246) aaaeee
(c.246) aaaaee (d.246) aaaaaa
Q.247 The odd decomposition of carbon chlorine bond form
(a.247) Two free ions (b.247) Two-carbanium ion
(c.247) Two carbanion (d.247) A cation and an anion
Q.248 A new carbon-carbon bond formation is possible in
(a.248) Cannizzaro reaction (b.248) Friedel-Craft's alkylation
(c.248) Reimer-Tiemann reaction (d.248) Both (b) and (c)
Q.249 An isomer of C3H6Cl2

on boiling with aqueous KOH gives acetone.
Hence, the isomer is
(a.249) 2, 2-dichloropropane (b.249) 1, 2-dichloropropane
(c.249) 1, 1-dichloropropane (d.249) 1, 3-dichloropropane
Q.250 Which of the following is the example of SN
2
reaction
(a.250)
3 3
CH Br OH CH OH Br

+ +
(b.250)
3 3 3 3
| |
CH CHCH OH CH CHCH Br
Br OH

+ +
(c.250)
2
H O
3 2 2 2
CH CH OH CH CH

=
(d.250)
3 3
| |
3 3 3 3
| |
CH CH
CH C CH OH CH C O CH Br
Br H

+ +


Testeleven

Q.251 Wurtz reaction of methyl iodide yields an organic compound X. Which
one of the following reactions also yields X

(a.251) C2H5Cl + Mg
dryether

(b.251) C2H5Cl + LiAlH4

(c.251) C2H5Cl + C2H5ONa
(d.251) CHCl3
Ag powder
A

Q.252 Ethyl orthoformate is formed by heating with sodium ethoxide
(a.252) CHCl3 (b.252) C2H5OH
(c.252) HCOOH (d.252) CH3CHO
Q.253 1 , 2 di-bromo cyclohexane on dehydro halogenation gives
(a.253) (b.253)
(c.253) (d.253) None of these
Q.254 In which one of the following conversions phosphorus pentachloride
is used as a reagent
(a.254) H2C = CH2 CH3CH2Cl
(b.254) H3C O CH3 CH3Cl
(c.254) CH3CH2OH CH3CH2Cl
(d.254) Both (b) and (c)
Q.255 When but 3-en -2- ol reacts with aq. HBr, the product formed is......
(a.255) 3 - bromobut - 1- ene
(b.255) 1 - bromobut - 2- ene
(c.255) A mixture of both a and b
(d.255) 2 - bromobut - 2 - ene
Q.256 Which of these do not form Grignard reagent
(a.256) CH3F

(b.256) CH3Cl
(c.256) CH3Br (d.256) CH3I
Q.257 An organic compound A(C4H6Cl) on reaction with Na/diethyl ether
gives a hydrocarbon, which on monochlorination gives only one chloro
derivative. A is......
(a.257) t-butyl chloride (b.257) s-butyl chloride
(c.257) Isobutyl chloride (d.257) n-butyl chloride
Q.258 Among the following the most reactive towards alcoholic KOH is......
(a.258) CH2 = CHBr (b.258) CH3COCH2CH2Br
(c.258) CH3CH2Br (d.258) CH3CH2CH2Br
Q.259 Which one of the following possess highest m.pt.
(a.259) Chlorobenzene (b.259) o-dichlorobenzene
(c.259) m-dichlorobenzene (d.259) p-dichlorobenzene

Q.260 Which chlorine atom is more electronegative in the following
(a.260) CH3-Cl (b.260) CH3 CH2 - Cl
(c.260)
3
|
|
3
CH
H C Cl
CH
(d.260)
3
|
3 2
|
3
CH
CH CH C Cl
CH

Q.261 What would be the product formed when 1-Bromo-3-chloro
cyclobutane reacts with two equivalents of metallic sodium in ether
(a.261) (b.261) (c.261) (d.261)
Q.262 Preparation of alkyl halides in laboratory is least preferred by
(a.262) Halide exchange
(b.262) Direct halogenation of alkanes
(c.262) Treatment of alcohols
(d.262) Addition of hydrogen halides to alkenes
Q.263 An alkyl halide may be converted into an alcohol by
(a.263) Addition (b.263) Substitution
(c.263) Dehydrohalogenation (d.263) Elimination
Q.264 The C-Cl bond in chlorobenzene as compared with C-Cl bond in
methyl chloride is......
(a.264) Longer and weaker
(b.264) Shorter and weaker
(c.264) Shorter and stronger
(d.264) Longer and stronger
Q.265 A salt solution is treated with chloroform drops. Then it is shaked
with chlorine water. Chloroform layer becomes violet. Solution
contains
(a.265)
2
NO ion

(b.265)
3
NO ion

(c.265) Br
-
ion (d.265) I
-
ion
Q.266 The following reaction belongs to (CH3)3C Br
2
H O
(CH3)3-C-OH
(a.266) Elimination reaction (b.266) Substitution reaction
(c.266) Free radical reaction (d.266) Displacement reaction
Q.267 The order of reactivities of methyl halides in the formation of
Grignard reagent is
(a.267) CH3I > CH3Br > CH3Cl
(b.267) CH3Cl > CH3Br > CH3I
(c.267) CH3Br > CH3Cl > CH3I
(d.267) CH3Br > CH3I > CH3Cl

Q.268 Identify Z in the following series

2
Br Alco. KOH KCN
2 5
C H I X Y Z
(a.268) CH3CH2CN (b.268)
2
2
CH CN
CH CN

(c.268) BrCH2 CH2CN (d.268) BrCH = CHCN
Q.269 The total number of stereoisomeric forms of C6H6Cl6 known is......
(a.269) 6 (b.269) 7 (c.269) 8 (d.269) None of these
Q.270 The correct order of C X bond polarity is......
(a.270) CH3Br >CH3Cl > CH3I
(b.270) CH3I > CH3Br > CH3Cl
(c.270) CH3Cl > CH3Br >CH3I
(d.270) CH3Cl > CH3I > CH3Br
Q.271 The order of reactivities of the following alkyl halides for a SN
2

reaction is......
(a.271) RF > RCl > RBr > RI
(b.271) RF > RBr > RCl > RI
(c.271) RCl > RBr > RF > RI
(d.271) RI > RBr > RCl > RF
Q.272 Which of the following reactions doesnt give benzene
(a.272) C6H5N2Cl
boiling
H O
2

(b.272) C6H5N2Cl
C H OH
2 5
A

(c.272) C6H5N2Cl + H3PO2 + H2O
(d.272) All of these
Q.273 Benzene hexachloride is prepared from benzene and chlorine in
sunlight by
(a.273) Substitution reaction (b.273) Elimination reaction
(c.273) Addition reaction (d.273) Rearrangement
Q.274 Carbon-halogen bond is strongest among the following
(a.274) CH3Cl (b.274) CH3Br
(c.274) CH3F (d.274) CH3I
Q.275 Which of these do not undergo Wurtz reaction
(a.275) C2H5F (b.275) C2H5Br
(c.275) C2H5Cl (d.275) C2H5I
Q.276 When ethyl bromide reacts with sodium acetylide the main product
is......
(a.276) 1-butane (b.276) 1-butene

(c.276) 1-butyne (d.276) 2-butene
Q.277 C2H5I and Ag2O reacts to produce
(a.277) C2H6 (b.277) C2H5 - C2H5
(c.277) C2H5 O- C2H5 (d.277) C2H5 CH3









#Solution#
Introduction of Halogen containing compounds

#2# % of Br
Mass of Br
100
Mass of organic compound
=


80
100 73.39%
109
= = or approx. 75%
#3# Gem-dihalides are those in which two halogen atoms are attached on
the same carbon atom.
#6# Isopropyl chloride
o
2
3 3
|
CH CH CH
Cl
chlorine atom is attached to 2
carbon atom.
#7#
3H
4 3
3X
CH CHX

+
(X = Cl, Br, I)
#11# Neohexyl chloride is a primary halide as in it Cl-atom is attached to a
primary carbon.

3
|
3 2 2
|
3
CH
CH C CH CH Cl
CH


#12#



13. (b)
o o
o o o
o
o
1 1
3 3
1 | | 2 1
3 2 3
3
4 |
3-chloro-2,3-dimethylpentane
CH CH
CH CH C CH CH
Cl


Preparation of Halogen containing compounds
#15#
|
3 2 3 3
| |
3 3
2-bromo, -2-methyl propane
Br
CH CH CH HBr CH C CH
CH CH
= +
#18# CH3COOAg + Br2
2
CS
CH3Br + AgBr +CO2
#20# C2H5OH+SOCl2
Pyridine
C2H5Cl+SO2+HCl
#27#CH2=CH2+BR2
3
CH OH

2 2 2 2 3
| |
CH CH Br CH CH O CH
Br Br
+
#28# C3H8 + Cl2
Light
C3H7Cl + HCl
This is an example of substitution reaction. Hydrogen atom of alkane
is replaced by halogen atom.
#29# CH CH + HCl CH2=CHCl
HCl +
CH3CHCl2
#30# R-OX+HX R-X+H2O
Reactivity order of alcohols for this reaction
3 > 2 >1


Reactivity order of halogen acids
R-I > R-Br > R-Cl
#31#
U.Vlight
6 6 2 6 6 6
Benzene BHC
C H 3Cl C H Cl +

#32#
#34#
2 3
KI
2 5 3
Na CO
C H OH CHI
#35#
2 2 2 2
Bleachingpowder
CaOCl H O Ca(OH) Cl + +
#36#
Hydrolysis
2 2 2 2
CaOCl H O Ca(OH) Cl + +

Oxidation
3 2 2 3
CH CH OH Cl CH CHO 2HCl + +


Chlorination
3 2 3
CH CHO 3Cl CCl CHO 3HCl + +




#37#
Boil
3 3
Chlorol Chloroform
CCl CHO NaOH CHCl HCOONa + +
#38# CaOCl2 + H2O Ca(OH)2 +Cl2

3 3 2
|
2-propanol
CH CH CH Cl
OH
+
3 3
||
CH C CH 2HCl
O
+

3 3 2 3 3
||
CH C CH 3Cl CCl CO CH 3HCl
O
+ +



#39# CH3CH2OH+Cl2 CH3CHO+2HCl

3 2 3
Chloral
CH CHO 3Cl CCl CHO 3HCl + +
#40#
2 5 2 5 2 5 2
Ethyliodide
C H O C H 2HI 2C H I H O + +
#42#
2
NaOH/ I
3 2 2 3
CH CH CO CH CH No yellow ppt

2
NaOH/ I
3 3 3
CH COCH CHI

2
NaOH/ I
2 5 3
C H OH CHI

2
NaOH/I
3 3 3
|
CH CH CH CHI
OH

#43#
2
NaOH
3 6 5 3
|| I
Yellow ppt.
Acetophenone
COONa
CH CC H CHI
O
+
#44# CH3COCH3 + 3I2 +4NaOH
CHI3+3Na+CH3COONa+3H2O
#45#
Pyridine
2 5 2 2 5 2
C H OH SOCl C H Cl SO HCl + + +

#46#
#47#
2
ZnCl
3 3 2
CH OH HI CH I H O + +
yellow ppt.


#48#
Dry ether
2 5 2 5
Ethyl iodide Ethyl magnesium iodide
C H I Mg C H Mg I +
#56#
3 2 3 3 Marko wnikoff's
|
rule
CH CH CH HBr CH CH CH
Br
= +

#58# DDT is prepared by heating chlorobenzene and chloral with
concentrated sulphuric acid



#59# Acetone forms chloroform when heated with bleaching powder.
CaOCl2+H2O Ca(OH)2+Cl2
CH3COCH3+3Cl2 CCl3COCH3+3HCl

3 3 2 3 3 2
chloroform
2CCl COCH Ca(OH) 2CHCl (CH COO) Ca + +
#60#
2 2 2 2
Bleaching powder
CaOCl H O Ca(OH) Cl + +
Cl2+H2O 2HCl+O

2 5 3 2
ethanol Acetaldehyde
C H OH O CH CHO H O + +

3 2 3
chloral
CH CHO 3Cl CCl CHO 3HCl + +

3 2 3 2
chloroform or
trichloromethane
2CCl CHO Ca(OH) 2CHCl (HCOO) Ca + +
#61# CaOCl2+H2O Ca(OH)2+Cl2
CH3CH2OH+Cl2 CH3CHO+HCl

2
Ca(OH)
3 2 3 3 2
CH CHO Cl CHCl (CH COO) Ca + +
#62# When ethylene reacts with bromine, it forms ethylene dibromide.

2 2 2 2 2
| |
Ethylene Bromine
Ethylene dibromide
H C CH Br H C CH
Br Br
= +
#63# The chlorination of alcohol by SOCl2 (thionyl chloride) is the best
method for the preparation of alkyl halides as in this method all the

other product are gaseous and thus halides are obtained on quite
pure state
2 2
R OH SOCl R Cl HCl SO
A
+ + | + |
#64#
#65# DDT is formed by reaction of chloral with chloro benzene.
#67# NBS is a selective brominating reagent since it normally brominates
the ethylenic compounds in the allylic position.

Properties of Halogen containing compounds
#68#
As CCl3 is a m-directing group.
#69# Ag2O+H2O 2AgOH
C2H5Br+AgOH C2H5OH+AgBr
#70#
Dry
2 5 2 5 2 5 2 5
Ether
C H Cl 2Na ClC H C H C H 2NaCl + + +
#71#
3 2 5
NH C H Cl
2 5 2 5 2 2 5 2
C H Cl C H NH (C H ) NH

2 5 2 5
|
C H Cl C H Cl
2 5 3 2 5 2 5
|
Tetraethyl ammoniumchloride
C H
2 5
(C H ) N C H N C H Cl
C H
2 5
+

(
(
(

(
(
(


If NH3 is in excess, then 1 amine will be the main product, if C2H5Cl
is in excess then mixture of 1,2,3 and quaternary amine is
obtained.
#72#
Light
3 2 2
air
Phosgene
2CHCl O 2COCl 2HCl + +
#73# COCl2 carbonyl chloride is commonly called as phosgene.
#74# C2H5NH2 + CHCl3+3KOH

2 5 2
Ethylisocyanide(offensive odour)
C H N C 3KCl 3H O = + +
#75#
Dry
3 3
Ether
Methyl chloride
|
3
Isopropyl chloride
CH CH Cl 2Na Cl CH
CH
+ +


3 3
|
3
Isobutane
CH CH CH 2NaCl
CH
+
#76#
Dry ether
RX Mg R Mg X +
#78#
2 5 6 5 2
more reactive less reactive
C H Cl C H CH Cl >
#80# Chlorobenzene is less reactive than benzyl



chloride

In chlorobenzene the lone pairs present on Cl atom get involved in
resonance with electrons of benzene due to which C-Cl bond acquires
double bond character Hence, reactivity decreases.

#81# CH3-Cl> CH3-CH2-Cl>

#82# CHI3

gives a yellow ppt. of AgI.

#84# O H NaCl NaOH CCl
2 4
2 4 4 + + +


#85#
Dry
ether
Grignard's reagent
RX Mg R Mg X +
(X=Cl,Br,I)

#86#
3
|
Elimination
3 3
|
3
CH
CH C Br CH ONa
CH
+

3
|
3 2 3
Isobutylene
CH
CH C CH CH OH NaBr = + +
CH3ONa CH3O
-
+Na
+

methoxide ion (CH
3
O
-
) is a strong base, therefore it abstract proton
from 3 alkyl halide and favours elimination reaction.
#87#
3 2 3 2 2
Chloropicrin (war gas)
CHCl HO NO CCl NO H O + +
#88# CCl4 +AgNO3 No reaction
CCl4 is a covalent compound. Therefore does not provide Cl
-
ions.
#89#


#90# C6H5 - CH2 Cl + KCN(aq) C6H5 - CH2 C N + KCl
#91#

#92#
#94#




#95#

#96#
2 2
Hydrolysis
| |
2 2
CH F CH OH
CH F CH OH

#97#
#99# CCl4 is a covalent compound, Hence it does not give Cl
-
ion in
solution.
CCl4 + AgNO3No reaction

#100#
#101#
2 5 2 5 4
Tetra Ethyl lead
(TEL)
4C H Br 4Pb / Na (C H ) Pb 4NaBr + +
#102#
3 3
Acetylene
CHI 6Ag I CH CH CH 6AgI + + +

#103#

Ag-O-N=O is a covalent compound. Therefore, attack of
nucleophile occurs through Nitrogen atom. Hence, nitroethane is
formed.
#107# C2H5Br
KCN(X)
C2H5CN
4
LiAlH (Y)
C2H5CH2NH2(C3H7NH2)
X=KCN,Y=LiAlH4

#108# CH3CH2CH2CH2 Cl + KOH(alc.)
3 2 2 2
1-butene
CH CH CH CH KCl H O = + +
#109#
Zn
2 2
CH Br C C CH Br
A
CH2=C=C=CH2
#110#
2 5 2 3 2 5
ethyl amine Reaction Ethylisocyanide
(Unpleasant smell)
C H NH CHCl 3KOH C H N C + + =
+3KCl + 3H2O



#111#

#113#
#114#
2 5 2 5
Ethyl isocyanide
(X)
C H Cl AgCN C H N C AgCl + = +
The functional isomer of ethyl isocyanide is ethyl cyanide C2H5-CN.

#115# C2H5Br+alc.KOH C2H4+H2O+KBr

#116#
Sunlight
3 2 2
Phosgene or carbonyl chloride
1
CHCl O COCl HCl
2
+ +
#117#
NaOH
6 5 2 6 5 2
(aq)
C H CH Cl C H CH OH
3
dil HNO
6 5
C H CHO
White ppt of AgCl are obtained.
#118#
2 3 2
A
C Cl OH Fehlingsol. Cu O
Red ppt
+
It means CHO group is present.

Oxidation
2 3 3
A Monocarboxylic acid
C Cl OH CCl COOH
It means only one CHO group is present.
C2H5OH+Cl2CH3CHO+2HCl

3 2 3
Chloral
CH CHO 3Cl CCl CHO 3HCl + +
#120# Ethanol cannot undergo dehydrohalogenation.
#121#
6 5 2 3
(Aniline)
X
C H NH CHCl 3NaOH + +
2 6 5
Phenyl isocyanide
3NaCl 3H O C H N C + + =
#122#





#123# C2H5Cl+KCN
Hydrolysis
2 5 2 5
Ethyl cyanide Propanoic acid
(X) (Y)
C H CN C H COOH
#124#
2
NaOH
2 5 3
I
C H OH CHI
#125#

#126#
#127#
3 3 3 2 2
Chloroform Chloropicrin
CHCl conc. HNO CCl NO H O + +
#128# Before using the sample of chloroform as an anaesthetic, it is tested
by treating with aq. solution of AgNO3. A pure sample does not give
ppt with aq. AgNO3.
#129# Alkyl halide gives alkene on elimination, reaction takes place in
presence of alc. KOH.
CH3CH2Br+Alc.KOHCH2=CH2+KBr+H2O
There are two types of elimination reactions.
(a) E1 Unimolecular elimination
(b) E2 Bimolecular elimination
#130# (i) Ethyl alcohol (ii) Phenol

2 5 2 5
(aq)
Ethyl alcohol
C H Br NaOH C H OH NaBr + +



#131#
3 2 2 3
|
CH CH CH CH CH KOH
Br
+
2 5
C H OH
3 2 3
Elimination
2-Pentene
reaction
CH CH CH CH CH =
When alkyl halide reacts with alc. KOH then it favours elimination
reaction (Dehydrohalogenation). Since, trans pentene-2 is more
symmetrical than cis isomers. Hence, it is main product.

#133#
hv
3 2 2 2 2
CHCl O COCl Cl H O + + +
#137# Alkyl halide reacts with Mg in presence of dry ether to give alkyl
magnesium halide which is also called as Grignard reagent. This
reaction is also called as Grignards reaction.

dry
ether
Grignard's reagent
R X Mg R Mg X +
#138#
alc. KOH
3 2 2 3 2
CH CH CH Br CH CH CH
(A)
=

aq.KOH
3 3 3 3
| |
Propan-2-ol
CH CH CH CH CH CH
Br OH


#143#
2 5 2 2 5 2
nitro ethane
C H Br alc. AgNO C H NO AgBr + +

2 5 3 3 2 5
Ester
C H Br CH COOAg CH COO C H AgBr + +
#146# If CHCl3 sample contains phosgene (COCl2) then it will give a white ppt.
When treated with cold AgNO3.
#147# Because
3 2 2 2 3
| |
3 3
CH CH CH CH CH CH CH
CH CH
has four methyl groups
on the corner so it can produce for derivatives.
#151# CHCl3 + AgNO3 No react
CHCl3 is a covalent compound. It does not ionize in water.
#153# Vinyl chloride is less reactive than allyl chloride due to resonance
effect.
Order of nucleophilicity amongst the halide ion are as I
-
>Br
-
>Cl
-
.
#154#
3 2 2
Phosgene
CHCl O COCl HCl + +
#156#
2 3 2
1,1 dichloro ethane
CH CH Cl HCl CH CHCl

= +
#158#
Pd
3 2 3
Reduction
CH COCl H CH CHO HCl + +
HBr

#159#
3 3 2 6 2
CH Br Zn BrCH C H ZnBr
A
+ + +


#160#
#161#
3 2
Potassium formate
CHI 4KOH(aq.) HCOOK 3KCl 2H O + + +
#162# CHCl3 + 6Ag + Cl3CH CH CH + 6AgCl
#163# CO is poisonous gas.
#165# C6H6Cl6 + 3KOH C6H3Cl3 +3KCl +3H2O
Thus Benzene hexahalides decomposes when heated with alc. KOH
and yield trichloro benzene.
#166# C2H5-I + AgNO3C2H5ONO2+AgI
#167# We know that CHCl3+HF CHF3+3HCl. Thus in this reaction the
compound obtained in fluoroform (CHF3). As we know molecular
weight of CHF3 =70.
#169#
2
Dry ether
I powder
RX Mg R Mg X +
#170# Density of alkyl halide increases as the size of halogen atom
increases.
RF< RCl< RBr < RI
#171# Due to resonance partial double bond character is created on vinyl
chloride. So, chlorine atom is not replaced easily.
#172#
Nucleophile
or base
R X OH R OH X

+ +
#175#










+ 3NaOH

CCl
3
+ 3NaCl

C(OH)
3
COOH

+ H
2
O
NaOH

COONa

H
2
O +
+Cl
2
CH
3
Toluene

Sunlight

CH
2
Cl
+HCl

CCl
3

+2HCl
+ 2Cl2
Sunlight


#176#
#177# It is Wurtz reaction in which hydrocarbon formed when alkyl halide
react with Na metal in dry ether.

|
ether
3 3 3
2 chloro propane chloro
methane
Cl
CH CH CH CH Cl 2Na + +
3
|
3 3
2 methyl propane
CH
CH CH CH 2NaCl +
#178# C3H7Br+KCNC3H7CN+KBr
In IUPAC system the carbon of functional group also take in
numbering. So C3H7CN is butane nitrile.
#179# It is Wurtz fittig reaction

Na
6 5 3 6 5 3
Ether
C H Br CH Br C H CH 2NaBr + +
#180# Because it float over chloroform and prevent its oxidation.
#181# Due to the presence of electron rich methoxy group (+I) at p-position
the polarity increase on C-X bond by which it becomes more reactive
towards nucleophillic attack of ethanol, p-nitro and chloro are
electron deficient group decrease the polarity of C-X bond. Hence by
them it become difficult to react with ethanol due to less polarity.
Methyl group is less electron rich than methoxy group.
#182# When chloroform is treated with concentrated nitric acid, its
hydrogen is replaced by nitro group.

3 2 2 3 2
chloropicrin
CHCl HONO CNO Cl H O + +
#183# Alkyl halides give alkane when react with sodium in ether. This is
called Wurtz reaction.

ether
alkane
R Cl 2Na R Cl R R 2NaCl + + +
#184# Chloroform is oxidised to a poisonous gas, phosgene (COCl2) by
atmospheric gas.
CHCl3 + O COCl2 + HCl
#185# When chloroform reacts with HNO3 product formed are chloropicrin
or tear gas and water.

3 3 3 2 2
water chloroform conc. chloropicrin
CHCl HNO CCl NO H O + +
#186# We know that
CH3CH2Cl+KOHCH2=CH2+KCl+H2O
Thus in this reaction ethene ) (
4 2
H C is produced.

#187# We know that

heat
3 3
Acetylene
chloroform chloroform
HCCl 6Ag Cl CH HC CH 6AgCl + + +
Thus in this reaction acetylene (HCCH) is produced.
#188# Alkyl halide on reaction with dry silver oxide furnish ether.

3 2 3 3
(methoxy methane)
2CH Cl Ag O CH OCH 2AgCl
A
+ +
#189# Acylation or alkylation of aromatic compound in presence of AlCl3 is
known as Friedal-craft reaction.

3
dry
6 6 3 6 5 3
AlCl
Benzene chloro Toluene
methane
C H CH Cl C H CH HCl + +
#190# Any substance which when added to a chemical reaction inhibit or
decrease the rate of reaction is called negative catalyst. In CHCl3
when two percent ethanol is added, it stops the formation of carbonyl
chloride. So ethanol acts as negative catalyst.
#191# When benzene is heated with chlorine in the presence of sunlight, it
form benzene hexachloride.




#192#
#193# It is a common method to prepare alkanes. Methane cannot be
prepared by Wurtz reaction.

3 3 2 6
ethane
CH Br 2Na BrCH C H 2NaBr + + +
#194# At room temperature iodoform is the yellow solid.
#195# Benzyl chloride are far more reactive than alkyl halide towards
nucleophilic substitution reaction due to the reason that the
carbocation formed after the removal of halide ion is stabilized by
resonance.



#196# On hydrolysis, ethylene dichloride gives ethylene glycol. While
ethylidine chloride give acetaldehyde.

aq. KOH
2 2 2 2
ethylene dichloride glycol
CH Cl.CH Cl CH OH CH OH
Benzene
+ 3Cl2
hv
Cl
Cl
Cl
Cl
Cl Cl
BHC
CH
2
Br
Ionization
Br

CH
2


CH
2


CH
2


CH
2




2
H O aq. KOH
3 3
ethylidine chloride
Cl OH
CH CH CH CH
Cl OH


3
acetaldehyde
CH CHO
#198#
3 2 3 3 2
(X)
CH NH CHCl 3KOH 3KCl CH NC 3H O + + + +
#199#
Dry
3 3 3 3
Ether
CH Br 2Na Br CH CH CH 2NaBr + + +
#200#
2 5 2 5
(aq)
C H Cl KOH C H OH KCl + +
#205# Alkyl halide is best converted to alkene by mean of elimination
reaction in form of dehydrohalogenation.

dehydrohalogenation
2 2 2
R CH CH X R CH CH =
#206#
3
3
3
|
CH O
3 2
CH OH
|
CH
H C C CH Br A
H

?
Alkyl halide is 1.
Keep in mind 1 halide give product by SN 2 / E 2 mechanism and 1
halide always gives substitution reaction except when strongly
hindered base is used.
ex.: With
3
|
( )
3
|
3
CH
CH C O
CH

it gives mainly elimination.

The reaction involves carbocation intermediate.
i.e.
3
|
2
3
|
(primary carbocation)
CH
CH C CH
H

but as it is a primary carbocation it will rearrange to give a tertiary
carbocation, which completes the reaction
3
|
3
|
3
teritiary carbocation
CH
CH C
CH

Stability of carbocation : 3 > 2 > 1 >
3
CH

It is because the stability of a charged system is increased by
dispersal of the charge. The more stable the carbocation, the faster it
is formed.
N.B. Rearrangement can be done in two ways.



Therefore,

#207# According to Saytzeff's rule, the major product will be that one which
contains more number of substituents around the double bond.

#208# (CH3)3COH + PhMgBr PhH + (CH3)3COMgBr
#209# R2CuLi + RXR-R+R-Cu+LiX
#210# CH3F, CH3Cl, CH3Br and C2H5Cl are gases at room temperature. CH3I
is a liquid at room temperature and solidifies at 66.5C.
#211# The alkyl halides are highly reactive, the order of reactivity is
Iodide > bromide > chloride > (nature of the halogen atom).
Tertiary > secondary > primary.
Thus 2-bromopropane is the given option.
#212# Grignard reagent gives addition reactions with compounds containing
C=O,-CN and C=S groups.




#213#
Formation of A is a electrophilic addition reaction
(i) HBrH
+
+ Br
-




2
CH CH =
(ii)
+
+
+
3 5 6
CHCH H C H




Formation of B is a free radical addition reaction
(i)
hv
HBr H Br
- -
+

(ii)

(iii)


Uses of Halogen Containing Compounds

#215#

#216#
#221# DDT

#224#
Polymeriza tion
2 2 n
Vinyl Chloride
|
Polyvinyl Chloride(PVC)
n(CH CH Cl) ( CH CH )
Cl
=
#225# Freon (CCl2F2) is an odourless, non-corrosive, non toxic gas which is
stable even at high temperatures and pressures. It has low b.Pt, low
specific heat and can be easily liquified by applying pressure at room
temperature. It is therefore, widely used in refrigerant (cooling agent)
in refrigerators and air conditioners.
#228#
0
3
HF 800 C
3 2
SbF 2HCl
2CHCl 2CHF Cl


Polymari
2 2 2 2 r
CF CF ( CF CF ) =
#231# Its vapours are non inflammable (i.e. do not catch fire). Hence used as
fire extinguishers under the name pyren.
#232# Iodoform is used as an antiseptic for dressing wounds. When it comes
in contact with skin (organic matter), Iodine is set free which
responsible for antiseptic action.
#233# Inhalation of CHCl3 vapours produces loss of consciousness and is
therefore, used as a general anaesthetic agent in surgery.
#235# CCl4 is stable to red heat. Its vapours are highly non-inflammable i.e.
do not catch fire. It is because of this property
4
CCl is used as a fire
extinguisher. But now a days its use as a fire extinguisher is
restricted because with water vaporous. It forms highly poisonous
phosgene gas

4 2 2
Phosgene
CCl H O COCl 2HCl + +

#236# Benzene hexachloride is an insecticide generally known as
gammexane. It is obtained by the following reaction




#238# Chlorofluorocarbon is used in air-conditioning and in domestic
refrigerators for cooling purposes. Its main drawback is this, it is
responsible for ozone depletion.
Critical Thinking Questions
#239# CH3Cl have one Cl atom which is more electronegative so it will have
highest dipole moment.
#240#

#241#
3 3
sp sp
3 2 3 2
(aq)
Ethyl alcohol
CH CH Cl KOH CH CH OH KCl + +
#242# As a result of resonance, the carbon-chloride bond acquires some
double bond character. Hence, vinyl chloride does not undergo
nucleophillic substitution reactions.
#243#
#244# % of chlorine
Mass of chlorine
100
Mass of organiccompound
=
Chloral (CCl3CHO)
106.5
100 72.20
147.5
= =
Pyrene (CCl4)
142
100 92.20
154
= = Highest
Gammexene (C6H6Cl6)
213
100 73.19
291
= =
#245# SN
2
Substitution nucleophilic bimolecular order of different alkyl
halides. 1

> 2

> 3


Benzene
+ 3Cl2
sunlight
Cl
Cl
Cl
Cl
Cl Cl
BHC

SN
1
Substitution nucleophilic unimolecular order of different alkyl halides,
3

>2

> 1

.
#246# aaaeee form is the most powerful insecticide form of C6H6Cl6.
#247#
Heterolytic bond fission
2 2
anion
cation
R CH Cl RCH Cl

+
Cl is more electronegative than C by which it form anion and
hydrocarbon form cation.
#248# New carbon-carbon bond formation take place in Friedel Crafts
alkylation and Reimer-Tiemann reaction. In Friedel Crafts alkylation
following mechanism involve

3
R Cl AlCl +
4
Alkyl carbonium ion
R AlCl HCl

+ +





Here new CC bond formed between carbon of benzene ring and alkyl
group.
Similarly in Reimer-Tiemann reaction.



Here new CC bond formed between carbon of benzene ring and CHO
group.
#249#
3 6 2
| |
boil
3 3 3 3
| aqueous 2KCl |
Unstable 2, 2 dichloropropane
(isomer of C H Cl )
Cl OH
CH C CH 2KOH CH C CH
OH Cl

+
2
||
H O
3 3
(Acetone)
O
CH C CH

A

#250# Only 1 alkyl halides, i.e. CH3Br undergoes SN2 reaction.

#251# Wurtz reaction gives ethane

dry
3 2 6
ether
2CH I 2Na C H 2NaI + +
Similarly C2H5Cl reduced by LiAlH4

to give ethane

4
LiAlH
2 5 2 6
C H Cl 2H C H HCl + +
#252#

+
H R


R

+
H R
+ AlCl
4

R
+ AlCl
3
+ HCl
OH
+ CHCl
3
+ 3NaOH
OH
CHO
+ 3NaCl + 2H
2
O
Salicylaldehyde

#253#
#254# CH3-O-CH3+PCl52CH3Cl+POCl3
CH3CH2OH+PCl5CH3CH2Cl+HCl+POCl3
So, both reaction carried out by PCl5
#255#
2
|
H
2 3 2 3
H O
But-3ene-2-ol
OH
H C CH CH CH [H C CH CH CH

= =
Br
2 3
H C CH CH CH ]

=

|
2 3 2 3
3 Bromobut-1-ene 1 Bromo but-2-ene
Br
H C CH CH CH Br CH CH CH CH = + =
#256# The CF bond energy is maximum in CH3F. Thus fluoride is the less
reactive to form the grignard reagent with Mg.
#257#)
3 3 3
| | |
ether
3 3 3 3
| 2Na | |
3 3
CH CH CH
2CH C CH CH C C CH 2NaCl
CH CH Cl
+


2
|
3 3
|
CH Cl
CH C CH
Cl

#258# The polarity between C-X bond increase by increasing the +I effect
which increase by increasing the alkyl group by which X of C-X easily
eliminate. In CH3CH2CH2Br the polarity is maximum due to 3 alkyl
group while in rest polarity decrease due to the presence of double
bond, presence of CO group (I) and less no. of alkyl group.

alc.
3 2 2
CH CH CH Br KOH +
3 2 2
CH CH CH KBr H O = + +
#259# p-dichlorobenzene molecule has symmetrical structure. It can fit well
in its crystal lattice. The intermolecular forces of attraction are
strong. Hence, it possesses highest melting point.
#260# Due to +I effect of 3 alkyl group in option (d), the chlorine atom
occupy the maximum charge in it so it is more electronegative.
#261# It is the example of Wurtz reaction.







+ Cl2
+ Cl2
all CH3 gives same monochloro
CH2Cl derivative, so it is tertiary
butyl alcohol
Br
Cl
2Na 2Na + 2e

Cl

..

Br
Br
1, 2 dibromo cyclohexane Cyclohex-diene
2HBr -
ogenation Dehydrohal


self evaluation test
#262# Direct halogenation of alkenes is not preferred because in it a mixture
of monohalogen, dihalogen, trihalogen and tetrahalogen substituted
product is obtained which is difficult to separate.
eg.
2 2
Cl Cl
4 3 2 2
CH CH Cl CH Cl

2 2
Cl Cl
3 4
CHCl CCl
#263#






#264# In chlorobenzene C Cl bond acquires partial double bond character
because of resonance.
#265# 2NaI +Cl22NaCl+I2 (Dissolves in CHCl3 to give violet colour)
Chlorine displaces iodine from salt. The iodine get dissolve in CHCl3
or CCl4 to produce violet colour.
#266#
2
H O
3 3 3 3
(CH ) C Br (CH ) C OH
Here Br

substitute by -OH group.
#267# Reactivity towards grignard reagent are as under CH3I> CH3Br>CH3Cl
#268#
2
Br alc.KOH
2 5 2 4 2 2
| |
C H I C H CH CH
Br Br


KCN
2 2
| |
Butene-1, 4-dinitrile
CH CH
CN CN


#269# C6H6Cl6 has 8 stereoisomer.
#270# The C-X bond polarity order are as under CH3Cl>CH3Br>CH3I
#271# The order of reactivity of alkyl holides for SN
2
reaction is
R-I>R-Br>R-Cl>R-F
#272#
2
Boiling
6 5 2 6 5 2
H O
C H N Cl C H OH N HCl + +


Not shown by alkyl halide
(saturated compound)
HX CH CH R + =
Alkene
2

HX CH CH R + =
Alkene
2

Addition
reaction
Dehydrohalogenation
Alc.KOH
Elimination
Alc.KOH
aq.KOH
Substitution
HX OH CH CH R +
Alcohol
2 2

2 2
Alkyhalide
R CH CH X


#273#
#274# CH3F>CH3Cl>CH3Br>CH3I
#275#
Dry
2 5 2 5
ether
C H F 2Na FC H No reaction + +
#276#
2 5 2 5
sodium acetylide sodium
Ethyl bromide 1-butyne
bromide
C H Br NaC CH C H C CH NaBr + +
Thus in this reaction 1-butyne is main product.
#277# C2H5I and Ag2O reacts as below

2 5 2 2 5 2 5 2
ether
2C H I Ag O C H OC H I + +
Thus, C2H5-O-C2H5 is produced.