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HKAL Passt Paper Questions

Q
:
Paart 11 Chemistry of
o Carbon
n Compou
unds
Naaming an
nd Isomerrisms
1. HKAL 19988 II Q5a
Consider the
t followingg compoundd F.

#(i)

Give the hybriidization stattes of the carrbon atoms a,


a b, c and d.

(ii)

Drraw all posssible three-diimensional structures


s
forr F, indicatinng the expeccted bond angles around the
caarbon atoms a, b, c and d in one of thee structures.
(5 marrks)

2. HKAL 19988 I Q4
Alcohol E has the struucture CH3CH
H(OH)C2H5.
a.

(i)

Drraw a three-ddimensional representatioon of E

(ii)

W type of isomerism
What
i
caan be exhibitted by E?
(2 marrks)

b.

(i)

Draw the structure of three structural isomers of E, all of which are alcohols.

#(ii)

Describe how the reagent Zn/concentrated HCl can be used to distinguish E from the three structural
isomers.
(3 marks)

c.

On treatment with dilute H2SO4(aq), E gives mainly two isomeric compounds, F and G, both of which have
the formula C4H8. On treatment with bromine, both F and G give a product H with formula C4H8Br2.
(i)

Draw structures for F, G and H.

(ii)

What is the isomeric relationship between F and G?


(4 marks)

3. HKAL 2008 II Q7a


Deduce the structure of isomeric compounds F and G, with formula C 6 H 12 , that have the following
characteristics:
Compound

Characteristics

It has a pair of enantiomers.


It loses its chiral centre after hydrogenation over Pt.

It reacts with Br2 to give a single compound.


It reacts with HBr to give a single achiral compound.
(6 marks)

4. HKAL 2009 II Q4a


The Table below lists the melting points and boiling points of cis-1,2-dichloroethene and
trans-1,2-dichloroethene:
(i)

Explain why, in 1,2-dichloroethene, the carbon-carbon double bond cannot rotate freely.

(ii)

Explain why
(I)

cis-1,2-dichloroethene has a higher boiling point, and

(II)

trans-1,2-dichloroethene has a higher melting point.


(6 marks)

5. HKAL 2010 I Q4
Dimethyl fumarate can be found in most leather products since it is commonly used as a mould inhibitor.
However, it was banned in Europe for all kinds of consumer goods in March 2009 because it was found to
cause skin allergies. Compound A is an isomer of dimethyl fumarate. The structures and melting points of
these two compounds are given below:

(a)

(i)

Name the type of isomerism involved.

(ii)

Explain why the melting point of A is lower than that of dimethyl fumarate.
(3 marks)

(b)

Both dimethyl fumarate and A can be hydrolysed to their corresponding dicarboxylic acids, B and D.

(i)
(ii)

Explain why the melting point of D is lower than that of B.


Explain why the H f of B is more negative than that of D.
(4 marks)

6. HKAL 20000 I Q5a


Consider the
t reaction:

c.

Drraw the strucctures of all possible


p
sterreoisomers off the productt.

d.

W
Would
the prooduct rotate a beam of plaane polarized
d light? Expllain your ansswer.

7. HKAL 20055 II Q7b


The three--dimensional structures of
o two 2-chloorobutanes (P
P and Q) aree shown beloow:

(i)

t difference, if any, in physical


p
prop
perties betweeen P and Q.
Coomment on the

(ii)

W P and Q exhibit
Will
e
the saame chemicaal properties?? Explain your answer.
(3 marrks)

8. HKAL 1992 I Q1a


There are several isomers of benzenedicarboxylic acid.
(i)

Draw the structures of all possible isomers of benzenedicarboxylic acid.

(ii)

One of these isomers is used to make terylene. Outline the reaction involved.

(iii)

On heating, one of the isomers gives a compound W, with formula C8H4O3. Give the structure of W.
(5 marks)

9. HKAL 1992 II Q7
A carboxylic acid P, with a relative molecular mass less than 100, contains C, 55.8%; H,7.0%; and O, 37.2%
by mass. An attempt to convert P to its methyl ester Q by prolonged refluxing of P with methanol in the
presence of aqueous H2SO4 gave the desired ester Q but with much of the starting material P unchanged.
a.

Determine the molecular formula of P.

b.

Give the structures of four carboxylic acids having the molecular formula you determined in (a). Give
the systematic names for any one of the carboxylic acids and its methyl ester.

c.

Suggest, with explanations, two ways which would make the esterification go towards completion.

d.

Which has a higher boiling point, the carboxylic acid or its methyl ester? Explain your answer.

e.

Show, using equations, how you would convert Q to P.


(17 marks)

10. HKAL 1994 II Q7a


What do you understand by the terms

structural isomerism and

stereoisomerism?
(3 marks)

11. HKAL 1994 II Q8c


Give a systemic name to each of the following compounds.
a.

CH3
CH3CH

CH3
CH

CH2CH=CH 2

b.

O
CH3CH2CH2-O-C-CH2CH2CH3
c.

O
CH3CH2-C-CHCH2CH3
OH
(3 marks)

12. HKAL 19996 II Q8b


The follow
wing compouunds can exist in isomeriic forms:
(i) butenedioic acid, annd
(ii) 2-aminnopropanoicc acid.
In each caase, state the type of isom
merism and draw
d
suitable representatiions for the isomers.
(4 marrks)

13. HKAL 19999 II Q6c


State the relationship
r
b
between
eachh pair of struuctures show
wn below:

(3 marrks)

10

14. HKAL 2002 II Q7b


For each of the following pairs of molecules, identify their relationship as identical, enantiomeric, geometrical
isomeric or structural isomeric.

(5 marks)

11

15. HKAL 2003 II Q6b


Compound A (C6H6O6) is an acyclic tribasic acid isolated from the leaves and tubers of Aconitum napellus.
Hydration of A gives two isomeric compounds, B and D. B is achiral, but D is chiral. Deduce the structures of
A, B and D.
(5 marks)

16. HKAL 2006 I Q6c


Answer the following multiple-choice question:
(i)

Which of the following compounds has a pair of enantiomers??

Ans: B

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17. HKAL 2006 II Q5c


Deduce the structure of compound D on the basis of the information given below:
(1)

Elemental analysis data show that D has the following composition by mass: C 40.0%, H 6.7%
and O 53.3%.

(2)

The relative molecular mass of D is estimated to be in the range of 172 to 182.

#(3)

The infra-red spectrum of D shows, apart from the absorption of CH stretching near

2900 cm-1, a

strong and broad absorption around 3400 cm-1, and no appreciable absorption around 1700 cm-1.
(4)

All carbon atoms of D have the same bonding environment.

(5)

D is highly soluble in water, and the solution does not decolorise bromine water.
(8 marks)

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18. HKAL 2006 II Q5b


Compound B is a strong stimulant.

Its structural formula is as follows:

(i)

Give the systematic name of B.

(ii)

In fact, the above structural formula can represent two stereoisomers.

(iii)

(I)

Draw three-dimensional structures of the two stereoisomers.

(II)

State a physical property which is different for the two stereoisomers.

It is known that among the two stereoisomers, only B has stimulant activity while the other one
does not. Why?

(iv)

A person is suspected to have taken stimulant B.

A urine sample of the person is sent for analysis.

Suggest a method to establish whether B is present in the urine sample.


(7 marks)

14

Alkanes and Alkenes


19. HKAL 1999 I Q5a
Under certain conditions, methane reacts with chlorine to give chloromethane as the major product.
(i)

State the conditions for the reaction

(ii)

Outline the mechanism and name the mechanistic steps of the reaction.

(iii)

Is the reaction of methane with chlorine an appropriate method for the preparation of dichloromethane?
Explain.
(5 marks)

(i)

(ii)

(iii)

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20. HKAL 2001 I Q5a


Consider the reaction:

(D is deuterium, as isotope of hydrogen)


(i)

Draw the structure of the major product.

(iii)

Is the product optically active? Explain your answer.


(3 marks)

(i)

(iii)

21. HKAL 2001 I Q6b


After some lessons in organic chemistry, a student remarked, Alkanes are more stable than alkenes, therefore
alkanes do not react with chlorine but alkenes do.
Do you agree with the student? Explain.
(3 marks)

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22. HKAL 2004 II Q6b


Hydrocarbons G reacts with HBr to give J as the major product.

(i)

Give the structure of J and its systematic name.

(iii)

A student commented that J obtained from the above reaction is optically active. Do you agree with
the student? Explain.
(5 marks)

(i)

(iii)

23. HKAL 2005 I Q6b (iii)


Which of the following statements concerning the hydrogenation of ethene is INCORRECT?
A.

The hydrogenation is an exothermic process.

B.

The hydrogenation occurs in the presence of a catalyst at room temperature.

C.

The H-H bond is weak to allow the hydrogenation to occur.

D.

Ethane is less energy rich than the starting materials.

Ans: C

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24. HKAL 2007 I Q5a (ii)


Give the structure of the major organic product E in the following reaction. Indicate the stereochemistry of the
products as appropriate.

(1 mark)

25.

HKAL 2007 II Q7b

Consider the following reaction:

(i)

Give the structure of the major organic product L.


(1 mark)

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26. HKAL 2009 II Q4b


Neoprene, a synthetics rubber, can be obtained from buta-1,3-diene via the following route:

#(i)

The reactant for Step 1 is Br2. Propose a mechanism for the formation of A from buta-1,3-diene.

(ii)

Suggest reactant(s) and conditions for each of Steps 2,3 and 4.

#(iii)

Explain why the strength of neoprene can be improved after heating it with sulphur.
(8 marks)

27.

HKAL 1995 II Q9b


Identify the following unknown structure.
M

CH2=CHCO2CH3 CH3CH2CO2CH3
(1 mark)
M: Pd or Ni or Pt / H2

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28. HKAL 1991 II Q7a


State with explanations, what you would observe in each of the following experiments, and write equations for
the reactions.
(i)

A mixture of pentane and bromine in tetrachloromethane is exposed to sunlight.

(ii)

Propene is bubbled into aqueous alkaline potassium manganate(VII).

(i) The reddish brown bromine turns colourless (1)


The reaction is a free-radical substitution reaction (0.5)
Depending on the amount of bromine, various substitution products are obtained.
CH3CH2CH2CH2CH3 + Br2 CH3CH2CH2CH2CH2Br or CH3CH2CH2CH2CHBr2 etc (1)
(ii) The purple colour of KMnO4 turns to colourless. (1)
KMnO4 is reduced and the alkene is oxidized. (0.5)

KMnO4
H3C

CH3CH=CH2

OH

OH

(1)

29. HKAL 1998 II Q5c


Give the structures of the major organic products, G and H, in (i) and (ii) below.
#Outline a mechanism for the formation of the major product in each of the three reactions.
(i)

(ii)

(2 marks)
CH3
(i)

G:

H3C

CH2CH3

Br

(ii)

H:

CH3CH2CH2OH

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Alkanols, Ketones/Aldehydes and Carboxylic acids


30. Show how you carry out the following conversions in the laboratory, giving the structures of intermediate
compounds and the reagents for each step.
a. HKAL 1995 II Q8b(ii)

OH
CH3CH2CH2OH

H3C

CH3

H
(3 marks)

b. HKAL 1996 II Q9a(iv)

OH

OH
OH
(3 marks)

21

31. Outline chemical tests which would allow you to distinguish between the compounds in the following pairs.
Describe what you would observe in each case.
a.

HKAL 1991 II Q9a (ii)


OH

COOH

(2 marks)
Add solution of NaHCO3 to the compound, C6H5COOH will react to give CO2 while the phenol C6H5OH will not.

b.

HKAL 1991 II Q9a (iv)


H

OH
CH3CH2CH2

CH3

CH3CH2CH2

CH3

CH2OH

C
CH3

(2 marks)
Warm the compounds with acidified K2Cr2O7.
The primary alcohol will turn the solution from orange to green while the tertiary alcohol will not.

c.

HKAL 1993 II Q8a(iv)


OH

CH2OH

CH3

(3 marks)
Warm the compounds with acidified K2Cr2O7.
The primary alcohol will turn the solution from orange to green while the tertiary alcohol will not.

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d.

HKAL 1995 II Q7a(iii)


CH3

CH2OH

OH

(4 marks)

e.

HKAL 1993 II Q8a(ii)


CH3CH2CH2CH2CHO

CH3CH2COCH2CH3
(3 marks)

Warm the compounds with acidified K2Cr2O7.


The aldehyde will turn the solution from orange to green while the ketone will not.

f.

HKAL 1996 II Q7c

O
C

(2 marks)

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32. HKAL 1996 II Q7b


In an experiment, 25 g of (CH3)3COH react with 36 g of HCl to gives 28 g of (CH3)3CCl.
(i)

Find the limiting reactant of the reaction,showing clearly

(ii)

Calculate the percentage yield of (CH3)CCl.

your calculation.
(3 marks)

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33. HKAL 2000 II Q7a


An acyclic compound, R(C7H12O) has a linear structure, R can be converted to S and then to T:
C7H12O
R

LiAlH4

C7H14O

H2/Pd

C7H16O
T

Given that R exists as a mixture of geometrical isomers, S has a chiral carbon center, and T does not have any
chiral carbon center, deduce all possible structures of R, S and T.
(8 marks)

25

34. HKAL 2001 I Q8b


In an experiment to prepare propanal from propan-1-ol,

CH3CH2CH2OH

Cr2O72- / H+

CH3CH2CHO

heat
a side-product N (C6H12O2) was formed.
(i)

What is N? Suggest how N is formed.

(ii)

Suggest one method to separate propanal from a mixture of propanal and N.

(iii)

Suggest two methods to confirm the identity of propanal.


(3 marks)

(i)

(ii)

(iii)

26

35. HKAL 2002 I Q5b


Suggest reagent(s) to accomplish each of the following single-step transformations:

(1 mark)

36. HKAL 2005 II Q6a


Formaldehyde (methanal) is one of the commonly found organic indoor air pollutants.
(i)

Suggest a source of household formaldehyde.

#(ii) The indoor air quality (IAQ) standard for formaldehyde has been set at 0.10 ppm by volume.
Calculate the maximum allowable quantity of formaldehyde, in gram in a room of volume 200 m3 at
298 K and 1.01 105 N m-2.
(You may assume that formaldehyde behaves as an ideal gas.)
(iii)

Some indoor air purifiers remove formaldehyde by chemical means. Suggest one chemical for the
removal of formaldehyde with the formation of less harmful products.

(iv)

Name one other organic indoor air pollutant and suggest its source.
(7 marks)

27

37.

Identify the following unknown structure.

a. HKAL 1994 II Q7

CH3CH=CHCH2CH2COOH

LiAlH4
(1 mark)

CH3CH=CHCH2CH2CH2OH

b.

HKAL 1995 II Q9b(ii), (iv)


(ii)
L
CH3CH2CH2COOH

CH3CH2CH2COCl

(1 mark)

(iv)

HOCH2CH2OH

OCH2CH2O
n

(1 mark)

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38. HKAL 2002 II Q7d


Suggest a synthetic route, in not more than three steps, for the transformation of 3-methylbenzoic acid to
N,N-diethyl-3-methylbenzamide, a substance commonly used in mosquito repellant.
CON(CH2CH3)2

CO2H

CH3

CH3

3-methylbenzoic acid

N,N-diethyl-3-methylbenzamide

(2 marks)

39. Identify the following unknown structure.


a.

HKAL 1993 II Q7a(iii)


NH2
CH3COCl

(1 mark)
O
H

C
N

b.

CH3

HKAL 1994 II Q7
NH2
CH3CH2COCl

(1 mark)
N

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40. HKAL 19997 II Q5b


The follow
wing equatioon representss the acid hyddrolysis of a dipeptide D to produce compounds E and F, onee of
which is chiral
c
compoound.

(i)

Name all functional groups in D.

(ii)

Give one struccture for E annd one for F.. Draw a suittable represenntation for thhe chiral product.

(iii)

Suuggest a methhod to separate E and F from


f
the reacction mixturee.
(5 marrks)

30

41. HKAL 2007 I Q4a, b


(a)

Consider the alkaline hydrolysis shown below:

Give the structure of product A.


(1 mark)
(b)

Consider the acidic hydrolysis shown below:

(i)

Give the structure of product B,

(ii)

Suggest the amount of acid required for the hydrolysis of 1 mole of the ester.

Explain

your answer.
(2 marks)
a.

b. (i)

(ii)

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42. HKAL 20009 I Q8


3-Methyl--l-butyl ethannoate, comm
monly knownn as isoamyl acetate, is a naturally occcurring com
mpound havinng a
distinctivee pleasant baanana odour and is used in food flav
vouring. In an experimennt to prepare the compouund,
5.0 cm3 of isoamyl alccohol is allow
wed to reactt with l5.0 cm
m3 of glacial acetic acid in the presen
nce of a reaggent
L.

(a)) Suggest what


w reagent L may be annd give the reeaction cond
ditions for thiis preparationn.
(l maark)
(b)) Calculate the mole rattio of isoam
myl alcohol too glacial aceetic acid usedd in this prepparation. (Giiven: densityy of
isoamyl alcohol=0.81 g cm-3; denssity of glaciaal acetic acid =1.05g cm-33)
(2 maark)
(c)) Draw a labbelled diagraam of the asssembly of appparatus used
d in this prepparation.
(2 maark)
(d)) What are the major coompounds present in the resulting
r
mix
xture at the end
e of this prreparation?
(l maark)
(e)) Outline thhe procedurees to isolate isoamyl
i
acetaate from the resulting miixture. (It is known that isoamyl acettate
cannot be effectively separated
s
froom the resultting mixture by fractionall distillation..)
(3 marrks)
(f)

w isoamyl alcohol is NOT used in excess


e
in thiss preparationn.
Suggest why
(l maark)

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33

43. HKAL 1991 II Q9b


Suggest a possible structure for each of the compounds J, K and L below and explain briefly your deductions.
(i)

J, C4H6O, on oxidation gives K, C4H6O2.


(2 marks)

(ii)

L, C5H12O, can exist as a pair of enantiomers, and reacts with phosphorus pentachloride to give
hydrogen chloride.
(2 marks)

(i)

(ii)

34

Important Organic Chemicals


44. HKAL 2002 II Q7c
A mixture of 2.8 g of butane-1,4-diol and 6.3 g of benzene-1,3-dicarbonyl chloride was heated at 215oC for 30
minutes to give 6.4 g of a polymer M.

COCl

HO(CH2)4OH

butane-1,4-diol

COCl

benzene-1,3-dicarbonyl chloride

(i)

Draw the repeating unit of M.

(ii)

What type of polymerization is involved in the formation of M?

(iii)

Calculate the percentage yield of M.


(5 marks)

35

45. HKAL 1997 II Q6b


Saponification of 1 mol of fat G with NaOH(aq) produces 1 mol of a triol C3H8O3, 2 mol of
CH3(CH2)16CO2-Na+ and 1 mol of CH3(CH2)14CO2-Na+.
(i)
(ii)
(iii)

If G is optically active, suggest its structure. Explain.


If G is optically inactive, suggest its structure.
What is the minimum number of moles of base required for the complete saponification of 1 mol of G?
(4 marks)

36

46. HKAL 19999 II Q5c


Dacron is the most com
mmon of thee group of poolymers know
wn as polyessters. A segm
ment of the po
olymer chainn is
shown bellow.

(i)

Suggest tw
wo types of material
m
which can be maade from pollyesters.

(ii)) Draw the structures of


o the two monomers
m
used in manuffacturing Dacron. Name the type of polymerizattion
involved.
(iiii) How can Dacron
D
be deegraded in thhe environmeent?
(5 marrks)

37

47. HKAL 1999 II Q6b


(i)

Draw the structure, showing two repeating units, for each of the following polymeric materials:
(I)

poly(chloroethene) and

(II)

cellulose

(ii) Large quantities of poly(chloroethene) and cellulose used in daily life, Suggest, with explanation, an
appropriate waste disposal method for each material.
(5 marks)

38

48. HKAL 20000 II Q6


a.

Sodium stearate CH3(CH


( 2)16CO2-Na
N +, the moost common soap, can be
b made by heating a trriglyceride with
w
sodium hyydroxide soluution.
(i)

Drraw the struccture of the triglyceride.


t

(ii)

W the help of equation((s), describe the


With
t chemistry
y when soapp is added to hard water.

(iii)

Exxplain why washing


w
sodaa, Na2CO310H2O, can help to reducce the hardneess the waterr.
(4 marrks)

b. Product J, frrom the transsformation beelow, is com


mmonly-used household detergent.
d

(i)

Drraw the struccture of J.

(ii)

Sttate one advaantage of usinng J as a dettergent.

(iii)

Sttate one enviironmental prroblem assocciated with th


he use of J.
(3 marrks)

39

c.

Dodecyl glucoside
g
is a new deterggent.

(i)

d
glucooside can be used in the cleansing
c
off oily dirts.
Exxplain why dedocyl

(ii)

Suuggest how dodecyl


d
glucoside can bee degraded in
n the environment.
(4 marrks)

40

49. HKAL 20005 II Q5b


Aspartame is a commoonly used arttificial sweettener.

(i)

n atom withh an
Coopy the structure of aspartame into your answerr book, and mark each cchiral carbon
assterisk.

(ii)

W referencee to its structture, explain why aspartaame is unstabble in cookinng.


With

(iii)

Inn a coffee shhop, a packett of sweeteneer contains about


a
5% off aspartame aand 95% of silicon dioxiide.
Suuggest a reasson for includding silicon dioxide
d
in th
he packet.
(4 marrks)

41

50. HKAL 2006 II Q7a


In the past, people chewed willow bark to ease their pain and to lower fever. Later on, chemists identified
salicin as the active ingredient in willow bark.

salicin
Salicin undergoes acid hydrolysis to give glucose and 2-hydroxybenzyl alcohol.
#(i)

Suggest a chemical test to distinguish between salicin and glucose.

Account for the difference in

results of your suggested test.


(ii)

2-Hydroxybenzyl alcohol can be converted in two steps to acetylsalicylic acid, which is the active
ingredient of aspirin.

2-hydroxybenzyl alcohol

acetylsalicylic acid

(I)

Give the reagents used in Step 1 and in Step 2.

(II)

In a typical experiment, 2.0 g of 2-hydroxybenzyl alcohol gives 2.0 g of acetylsalicylic acid.


Calculate the percentage yield of the conversion.
(7 marks)

42

51.

HKAL 2007 II Q6d


Polyethenne terephthalaate (PET) is a polymer used
u
in makin
ng clothing fibres
f
and sooft drink botttles.

The fllow

diagram below
b
shows a route for the
t synthesis of PET.

(i)

Give the reagent(s)


r
annd conditionss for each of Steps 1, 2, 3 and 4.

(ii)) Polyethenne naphthalatte (PEN) is a polymer forrmed from naaphthalic aciid and ethanee-1,2-diol.

(I)

o PEN.
Drraw the struccture of a reppeating unit of

(II)

W
Which
polymeer, PET or PE
EN, do you expect
e
to be more rigid?

Explain.
(6 marrks)

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52. HKAL 2010 II Q4d


Polyethylene terephthalate (PET) is a polymer commonly used in making soft drink bottles.
(i)

Suggest a synthetic route with no more than three steps to convert benzene-1,4-dicarbaldehyde
to PET. (You are NOT allowed to use organic reagents with more than three carbon atoms.)

(ii)

Suggest why PET as compared with polystyrene, is more readily degraded in the environment.
(4 marks)

44

M
Miscellaneo
ous
53. HKAL 20000 II Q6e
Identify L,
L M and N inn the followiing reactionss:

45

54. HKAL 2002 II Q5c


Consider the substances listed below:
butane

benzoic acid

dichlorodifluoromethane

ethanoic acid

hexane

polystyrene

propanone

tetrachloromethane

triethylamine

For each of the descriptions of physical properties from (a) to (h) below, choose from the above list, one
substance which best fits the description.
(i)

a colourless, flammable gas

(ii) a colourless liquid with a sour odour


(iii) a colourless, water miscible, flammable liquid
(iv) a colourless, non-flammable liquid
(v) a colourless liquid with a fishy smell
(vi) a colourless, water immiscible, flammable liquid
(vii) a white solid which is insoluble in both cold and hot water
(viii) a white solid which is insoluble in cold water, but soluble in hot water
(8 marks)

46

55. HKAL 2003 I Q6b


The weakest chemical bond in an organic compound always breaks first in a chemical reaction.
The above statement is not always true. Give one example for which the statement is true and one example for
which the statement is not true. Explain each case briefly.
(4 marks)

47