H2 Chemistry 9647
46
6.
Carboxylic Acids & Derivatives
.. 63
7.
Nitrogen
Compounds
.. 80
8. Group II
.. 99
Arenes
QUESTIONS
Name: _________________________________________
Class: 2T____
Arenes
1. Arenes
1. Which of the following sequences of bromination, nitration and oxidation is expected to give the
best yield for synthesis of 2-bromo-4-nitrobenzoic acid from methylbenzene?
A
bromination, nitration, oxidation
B
bromination, oxidation, nitration
C
nitration, oxidation, bromination
D
nitration, bromination, oxidation
[PJC H2 2013 / Q24]
2. When benzene reacts with bromine in the presence of iron (III) bromide, what is the type of
reaction?
A
Electrophilic substitution
B
Electrophilic addition
C
Free radical substitution
D
Free radical addition
[IJC H2 2013 / Q19]
3. Which compound cannot be made directly from methylbenzene?
A
CH3
B
CH2Cl
Cl
C
CH3
D
CO2H
Br
Arenes
A
B
C
D
in the intermediate
complex
planar
tetrahedral
tetrahedral
planar
7. Chlorine gas was heated with 1,3-dinitrobenzene in the presence of iron (III) chloride.
NO 2
NO2
Cl
Cl
Cl
NO2
Cl
NO 2
NO 2
C
Cl
NO 2
Cl
NO 2
D
Cl
NO 2
Cl
NO2
Cl
8. When compound W was heated with acidified KMnO 4, compound X was obtained.
Arenes
OH
OH
OH
OH
O
O
OH
OH
O
30 oC
D
Structured Questions
Arenes
1.
(a)
Complete the reaction scheme below by drawing the structures of the organic compounds
in the boxes provided.
CH3
C
CH3
step III
limited Cl2, uv light
CH3
CH2Cl
CH3
Cl
step I
CH3
or
step IV
CH2
CH3
C
CH3
CH3
H
NO 2
step V
step II
Br2(aq),
room
temperature
CH2Br
COOH
CH3
OH
NO2
(b)
Suggest reagents and conditions for steps I and II by completing the table below.
(c)
2. The molecule of benzene is a regular hexagon in which the electrons are described as being
delocalized.
(i) By using benzene as an example, explain, with the aid of a diagram, what is meant by the term
delocalized electrons in benzene.
(ii) Give one physical and one chemical property which arise due to this structure.
[MI H1 / IIB / Q1a]
CH2CH3
CH2CH3
Arenes
4-nitrobenzylchloride
State and describe the mechanism undergone during the conversion shown above.
[IJC 10/ II / Q4b]
Compound E, 2-methylbenzoic acid, is used as an intermediate for the synthesis of dyes and
pesticides.
5.
C
OH
C
OH
CH3
CH3
Compound E
Br
Compound F
(ii)
Another product, which is the isomer of compound F, is also formed in the reaction. Draw the
displayed formula of the product.
(iii)
Name the type of reaction and describe the mechanism for this reaction, including curly arrows
showing the movement of electrons, and all charges.
6. A hydrocarbon, Z, has the molecular formula, C8H10. It reacts with chlorine either in the presence of
uv light or in the presence of AlCl3.
Arenes
(a) Draw an isomer of Z which upon reaction with chlorine forms a monosubstituted product
capable of rotating plane of polarised light.
(b) One possible isomer of Z is 1,3-dimethylbenzene.
(i) Suggest the reagents and conditions for a reaction that could be used to distinguish between
1,3-dimethylbenzene and your answer in (a). You should describe what you will see for each
compound.
(ii)Suggest the structure of the mononitrated product which is most likely to be formed when
1,3-dimethylbenzene reacts with concentrated nitric acid.
[CJC 12/ CA/ Q2]
7.
The benzene ring usually resists chemical oxidation but the process may be accomplished
microbiologically. The bacterium Pseudomonas putida in the presence of air rapidly converts
benzene into compound R.
(a)
Using the [O] notation for the oxidation of organic compounds, write a balanced equation for
this oxidation.
(b)
(c)
In the structure of compound R, the two OH groups are on the same side of the plane of
the ring, i.e. the OH groups are in a cis arrangement.
Compound S is a trans isomer of compound R.
Draw the structure of compound S, showing clearly the trans arrangement.
[HCI 12/ II/ Q4(a)]
8.
NO2
NO2
Step 2
NO2
Step 3
O2 N
NO2
NO2
TNT
(C7H5N3O6)
Arenes
(i)
(ii)
Name the type of reaction and describe the mechanism for Step 1, including curly arrows showing
the movement of electrons, and all charges.
(iii)
Explain why compound A occurs in very small amounts in the products of Step 2.
CH3
NO2
O2N
A
(iv)
Explain why more rigorous conditions are necessary for Step 3 compared to Step 2.
Halogen Derivatives
3. Halogen
1 1 mole of an organic compound P undergoes elimination on reaction with ethanolic sodium
hydroxide to form 2 moles of HBr. What could P be?
A
Which set of reagents for step I and step II would be most suitable?
Step I
Step II
A Hot aqueous KOH
PBr3
B Hot KOH in ethanol
HBr
C Hot concentrated H2SO4
Aqueous bromine
D Hydrogen gas with nickel catalyst
Bromine in the presence of ultraviolet light
[AJC H1 / MCQ / Q21]
3 Experiments are carried out on three compounds,
P, Q and R. A sample of 0.01 mol of each compound H
is refluxed with 40 cm3 of 1 mol dm-3 of NaOH
(in excess). Excess aqueous silver nitrate is added
to the resulting mixture after acidification in each case
and the mass of the precipitate weighed. What is the
mass in grams, of the precipitate formed by each
compound?
P
Q
R
A
4.31
4.31
4.31
B
2.87
2.87
1.44
C
2.87
4.31
1.44
D
1.44
4.31
1.44
Cl
C
H
Cl
Cl
Cl
Cl
Cl
H
Cl
Cl
Cl
Halogen Derivatives
5 Which of the following statements best explains why fluoroalkanes are the least reactive
halogenoalkanes?
A Fluorine is much more electronegative than carbon.
B The F ion is the most stable halide ion.
C The CF bond is the most polar carbonhalogen bond.
D The CF bond is the strongest carbonhalogen bond.
[HCI / MCQ / Q25]
[HCI H1 / MCQ / Q24]
6 2,4,6-trinitrophenyl derivatives are bright yellow crystalline compounds that can be formed by
the following reaction.
B Electrophilic addition
D Nucleophilic addition
[IJC / MCQ / Q10]
7 Which one of the following, in alcoholic solution, produces a precipitate most rapidly when
warmed with aqueous silver nitrate?
A 1-chlorobutane
B 1-bromobutane
C 1-iodobutane
D chlorobenzene
[MI / MCQ / Q23]
8 Hydrogen bonding is not present in
A CH3Cl
B CH3NHCH3
C6H5OH
D C6H5COOH
[MI / MCQ / Q27]
9 A halogen compound S was boiled under reflux for some time with aqueous sodium hydroxide.
The resulting mixture was cooled, treated with dilute nitric acid, followed by the addition of
aqueous silver nitrate. No yellow precipitate was seen. Which one of the following could be
S?
Halogen Derivatives
11 Which one of the following compounds gives the greatest number of alkenes when it is reacted
with hot alcoholic potassium hydroxide?
A
B
RR' + 2NaX
Which of the following does not show the correct product when the stated reactants are
reacted together in a Wurtz reaction?
A
Br
CH3
CH3
2Na
2NaBr
Br
Cl
2Na
NaCl
NaBr
Br
D
Br
CH2Br
2Na
2NaBr
Halogen Derivatives
15 Which of the following halides will react most rapidly with aqueous sodium hydroxide?
A (CH3)3CI
B (CH3)3CBr
C (CH3)3CCl
D (CH3)3CF
[NYJC H1 / MCQ / Q17]
16 Organic compound X undergone the following successive reactions:
I reaction with hydrogen chloride
II boiling with aqueous sodium hydroxide
III reaction with hot concentrated phosphoric acid
The final organic product was ethene. Which of the following could most likely be compound X?
A Ethene
B Ethanol
C Chloroethane
D Ethanoic acid
[SRJC / MCQ / Q24]
[SRJC H1 / MCQ / Q19]
17 In the upper atmosphere, chlorofluoroalkanes (CFCs) are broken down to give chlorine but not
fluorine radicals. What is the best explanation for this?
A Fluorine is more electronegative than chlorine.
B The C-F bond is longer than C-Cl bond.
C The C-F bond is stronger than C-Cl bond.
D The chlorine atom is larger than the fluorine atom.
[SRJC H1 / MCQ / Q18]
18 In which of the following reactions is the inorganic reagent acting as a nucleophile?
A
Cl
Cl2
B
C
CH2=CH2
Cl2
+
CH2Cl
ClCH2CH2Cl
CH2I
KI
CH 3
HCl
KCl
HBr
CH 2Br
Br2
Halogen Derivatives
20 In which compound is the carbon-halogen bond most easily hydrolysed by NaOH (aq)?
A chlorobenzene
B bromopropane
C fluoroethane
D 2,4,6 trichlorobenzene
[TPJC H1 / MCQ / Q17]
21 Which sequence shows the wrong order of increasing ease of hydrolysis?
A CH3CH2Br < CH3CH2I < C6H5CH2Cl
B
C6H5CH2Cl < C6H5CH2Br < CH3CH2I
C CH3CH2F < C6H5CH2Br < CH3CH2I
D
CH3CH2Cl < CH3CH2Br < CH3CH2I
[VJC H1 / MCQ / Q23]
22 A reaction sequence is given below. Which one of the following structures represents the
product Q?
CHBrCH3 KCN
P
ethanol
Br
A
dil HCl
reflux
Br
CHCH3
CHCH3
CO2H
CO2H
HO C
Cl
CHCH3
CHCH3
CH2NH2
COOH
Cl
Halogen Derivatives
For each of the following questions, one or more of the three numbered statements 1 to 3 may
be correct. Decide whether each of the statements is or is not correct. The responses A to D
should be selected on the basis of:
A
B
C
D
1, 2 and 3
are correct
1
1 only is
correct
Structured Questions
1 Dylan was asked by his chemistry tutor to differentiate
the three compounds below.
Dylan suggested the following method:
Step 1: To each of the 3 unknowns, add 1 cm3 of aqueous NaOH.
Step 2: Then add 1 cm3 of aqueous silver nitrate.
Step 3: Followed by aqueous hydrochloric acid, until blue litmus turns red.
Identify and explain the three errors in Dylan's method.
[HCI / II / Q4 a (modified)]
2 Compound A, 1-chlorobutane reacts with ethanolic sodium cyanide to yield product, B.
(a) With the aid of equations, name and describe the mechanism of the reaction and give the
structural formula of B.
(b) Explain how the rate of this reaction changes when 1-chlorobutane is replaced by 1bromobutane.
[MI / II / Q6 a, b ]
3
The hydrolysis of the halogenoalkanes shows a trend which can be related to their bonding.
The table below shows the observations after aqueous silver nitrate is added to each
halogenoalkane sample.
Compound
Observations
Precipitate
forms
almost immediately
CH3CHICH2CH3
CH3CHBrCH2CH3
Precipitate forms after 2 minutes
CH3CHClCH2CH3
Precipitate forms after 10 minutes
(i) By quoting suitable values from the Data Booklet, explain the above observations for the
hydrolysis of halogenoalkanes.
(ii) Predict, with a reason, whether a precipitate will be formed when aqueous silver nitrate is
added to CH3CHFCH2CH3.
[NYJC H1 / IIB / Q6 d ]
4
(a) When propane, CH3CH2CH3, reacts with chlorine, two different monochloropropanes are
produced.
(i) What condition is used for this reaction?
(ii) Draw the displayed formula of the two products
(iii) State the type of isomerism shown in the two products.
Halogen Derivatives
(iv) When the two products are refluxed with ethanolic potassium hydroxide, a compound B was
formed, which could rapidly decolourise bromine in CCl4. Give the displayed formula of B, and
write a balanced equation for the reaction between B and bromine in CCl4.
(b) Chlorofluorocarbons, CFCs, are small alkane molecules where a few of the hydrogen atoms
have been replaced by chlorine atoms and fluorine atoms. What are CFCs used for, what
environment hazard do they pose, and how, chemically, does this hazard arise.
[YJC H1 / IIB / Q6 d, e ]
5 Ethylbenzene can react with chlorine in two ways, depending on the conditions of the reaction.
CH2CH3
(i) State the condition needed for reaction I.
CH2CH3
CH2CH2Cl
(ii) Describe a test to distinguish between
Cl2
Cl2
A and B. State the reagents, conditions,
and the observations for each compound.
reaction II
reaction I
Write balanced equations for any reactions
CI
that occur.
B
[YJC H1 / IIB / Q7 c ] A
6 The graph below shows the reaction between aqueous sodium hydroxide and
a solution of a saturated alkyl chloride at temperature ToC.
[NaOH]/ mol dm-3
0.1
Time
(a) Referring to the graph above, deduce the order of reaction with respect to sodium
hydroxide and RCl and hence write down the rate law.
(b) Is RCl most likely to be a primary, secondary or tertiary alkyl halide?
(c) Draw a labelled energy profile diagram for the reaction.
(d) Briefly explain how one of the graphs above may be obtained experimentally.
(e) Aqueous hydrochloric acid and (CH 3)2CCHCl are separately reacted with aqueous
sodium hydroxide. How would the rates of reaction of these two compounds compare
with the rate of reaction of RCl in (b) above? Give your reasons.
Halogen Derivatives
Essay Questions
1 Suggest methods by which the following pairs of compounds could be distinguished from each
other by chemical tests. The distinguishing of some of these pairs may rely on a preliminary
breaking-up of the compounds and subsequent testing of the reaction products.
1-bromo-1-phenylethane
2-bromoethylbenzene
[HCI / III / Q2 c i ]
(i) State the reagents and conditions for the above reaction.
(ii) State the type of hybridisation and the shape with respect to the carbon atom, C , before and
after the reaction.
Halogen Derivatives
(iii) Describe a chemical test that would distinguish compound Z from chlorobenzene.
[TJC / III / Q1 e ]
6
The table below lists some information about five compounds, two of which are
chlorofluorocarbons (CFCs).
Name
Structure
Flammability
Lifetime / years
CFC-11
CCl3F
No
75
CFC-12
CCl2F2
No
108
HCFC-22
CHClF2
No
22
HCFC-123
CHCl2CF3
No
HFC-152
CH3CHF2
Yes
2
(i) Arrange the above hydrochlorofluorocarbons (HCFCs) and hydrofluorocarbons (HFCs)
compounds in order of increasing boiling points. Explain your answer in terms of structure and
bonding.
(ii) Give one use of CFCs in every day life.
(iii) Explain why the use of CFC poses a problem to the environment.
(iv) Hydrochlorofluorocarbons (HCFCs) and hydrofluorocarbons (HFCs) are possible replacements
for CFCs. Which compound in the above table is the best choice? Explain your answer.
[TJC / III / Q3 a ]
7
Hydroxy Compounds
4. Hydroxy
1 When an organic compound Q was treated with phosphorus pentachloride, fumes of hydrogen
chloride were evolved. When Q was warmed with alkaline aqueous iodine, a yellow precipitate
was formed. Which of the following was Q?
A CH3COOH
B CH3COCH2CH3
C (CH3)3COH
D CH3CH(OH)CH2CH3
[AJC / MCQ / Q24]
2 The anti-bacterial drug tetracycline has the formula
Which statement about tetracycline is correct?
A It does not react with SOCl2.
B It reacts with sodium carbonate to liberate carbon dioxide gas.
C 3 moles of HBr is formed when 1 mole of tetracycline reacts in
an excess of aqueous bromine in the dark.
D It reacts with sodium metal to liberate H2 gas.
[AJC / MCQ / Q25]
3 The structures below represent cyclohexane-1,2-diol.
nucleophilic addition
electrophilic addition
[PJC H2 2011 / Q21]
Hydroxy Compounds
ONa
NO2 NO2
Hydroxy Compounds
10 Which of the following reagents can be used to distinguish between 2-methylphenol &
phenylmethanol?
A KMnO4/ H+
B K2Cr2O7 / H+
C Br2 (g), U.V light
D Na (s)
[NJC / MCQ / Q25]
11 1 mol Compound Z gives the following observations when reacted with the specific reagents.
(i) Decolourises aqueous bromine,
(ii) Forms yellow precipitate with alkaline aqueous iodine,
(iii)Liberates one mole of hydrogen gas when two moles of sodium is added
What could Compound Z be?
A CH2=CHCH2CH(OH)CH3
A
B
C
D
Step I
ethanolic NaOH, reflux
ethanolic NaOH, reflux
NaOH(aq), reflux
NaOH(aq), reflux
Step II
concentrated H2SO4, 170oC
NaOH(aq), reflux
ethanolic KOH, reflux
concentrated H2SO4, 170oC
[IJC H1 / MCQ / Q20]
Hydroxy Compounds
D Y and Z
[NJC / MCQ / Q27]
Hydroxy Compounds
19 Which one of the following formulae is the final product when CH 3CH(OH)CH2C(CH3)
(OH)CH2OH is heated under reflux with acidified aqueous potassium dichromate(VI)?
D
[NYJC / MCQ / Q24]
20 Compound Q was refluxed with aqueous sodium hydroxide and the resulting mixture was then
distilled. The distillate gave a positive tri-iodomethane test. The residue in the distillation flask,
after acidification, gave a white precipitate. Which of these could be Q?
A
CH3CH2COOCH2CH3
C
CH3CH2OCOC6H5
B
C6H5COOCH3
D
CH3CONHC6H5
[SRJC H2 2011 / Q26]
21 Which of the following alcohols produces only one alkene that displays cis-trans isomerism on
dehydration with hot concentrated sulphuric acid?
A pentan-1-ol
B pentan-2-ol
C pentan-3-ol
D butan-2-ol
[PJC / MCQ / Q28]
22 Experiments are carried out on three compounds P, Q and R. Equal volumes of 0.020 mol
samples of P, Q and R are separately reacted with an excess of zinc powder. The volumes of
hydrogen gas evolved at room temperature and pressure were recorded at 5 minutes interval.
The volumes of hydrogen gas evolved at the first 5 minutes were 100 cm3, 150 cm3 and 200
cm3. Which sequence of compounds matches these results?
100 cm3
150 cm3
200 cm3
A
P
Q
R
B
P
R
Q
C
Q
R
P
D
R
P
Q
[SRJC / MCQ / Q25]
23 The pinacol rearrangement involves the reaction of a diol in acidic conditions to form a
carbonyl compound as shown below.
Hydroxy Compounds
CH3
CH3
HO
CH3
O
H
OH
CH3
CH3
CH3
2, 3-dimethylbutane-2,3-diol
CH3
H2O
CH3
3, 3-dimethylbutan-2-one
CH2CH3
HO
OH
CH3
2,3-diphenylpentane-2,3-diol
A
B
O
O
C
CH2CH3
CH3
C
CH2CH3
CH3
D
O
O
C
CH2CH3
C
CH3
CH3
CH2
CH3
[PJC H2 2011 / Q25]
Hydroxy Compounds
A
B
C
D
P
acidified K2Cr2O7
zinc metal
concentrated H2SO4,
ethanolic NaOH
Q
dilute NaOH
dilute HCl
dilute NaOH
concentrated H2SO4
CC
OH
CH3CHCl
CH3CH(OH)
OH
D
OH
OH
Cl
CH2(OH)CH2
OH
28 Which one of the following compounds is not a product of the vigorous oxidation of
geraniol?
Hydroxy Compounds
29 The compound
reacts with
NaOH(aq) to form
D
[VJC H1 / MCQ / Q20]
31 Which one of the following will be formed when pentan-1,4-diol is distilled with hot acidified
potassium dichromate(VI)?
Hydroxy Compounds
A CH3COCH2CH2CHO
CH3COCH2CH2COOH
CH3CH(OH)CH2CH2CHO
[VJC H1 / MCQ / Q21]
D CH3CH2CH(OH)CH3
[YJC / MCQ / Q30]
For each of the following questions, one or more of the three numbered statements 1 to 3 may be
correct. Decide whether each of the statements is or is not correct. The responses A to D should
be selected on the basis of:
A
B
C
D
1, 2 and 3
are correct
1
1 only is
correct
Which of the following reagents can be used to distinguish between the following two
compounds?
1 Br2 (aq)
Na
[AJC / MCQ / Q38]
2 The relative molecular mass of the organic compound increases when ethanol reacts with
1 acidified potassium chromate(VI) solution followed by distillation.
2 acidified potassium manganate(VII) solution.
3 sodium bromide and concentrated sulphuric acid.
[ACJC H1 / MCQ / Q29]
3
KMnO4
C2H5Br
step H
C2H5OH
C2H5Cl
Hydroxy Compounds
Monomer A reacts with diphenol B to give a polymer as shown in the reaction scheme below.
Which of the following pairs of compounds give the same organic products when subjected to
a hot solution of acidified potassium manganate (VII)?
Which of the following compounds forms a yellow precipitate when warmed with alkaline
aqueous iodine?
1 Butan-2-ol
2 1-phenylethan-1-ol
3 2-phenylethanol
Hydroxy Compounds
What would be observed when the following reactions are carried out?
In each case, give the name or formula of the reaction product which is responsible for the
observation you have made.
(i)
Substance E with PCl5.
(ii)
Substance E with sodium metal.
(iii)
Substance F with hot acidified potassium manganate (VII).
(iv)
Suggest how E could be converted into F in the laboratory.
[IJC H1 / IIB / Q1 c ]
3
There are two different alcohols that have the molecular formula C 3H8O.
Hydroxy Compounds
Draw the displayed formula of the 2 isomers and suggest a chemical test that can be used to
distinguish them. Include any observations that would be seen.
[SRJC H1 / IIB / Q1 f ]
4
Suggest how the three alcohols (namely butan-1-ol; butan-2-ol and 2-methylpropan-2-ol) could
be distinguished from each other experimentally. Include observations where appropriate.
[TPJC H1 / IIB / Q10 c ]
Use the information below to identify the compounds A to E. Explain your reasoning.
Compounds A and B each has a relative molecular mass of 60 and an empirical formula of
C3H8O. During the reaction with acidified potassium dichromate (VI) solution, A forms only one
organic product, C. Under similar conditions, B produces compound D which can be further
oxidised to E.
[VJC H1 / IIB / Q7 a i ]
Essay Questions
Hydroxy Compounds
1 Suggest methods by which the following pairs of compounds could be distinguished from each
other by chemical tests. The distinguishing of some of these pairs may rely on a preliminary
breaking-up of the compounds and subsequent testing of the reaction products.
(i)
(ii)
[AJC / III / Q5 c i, ii ]
2 Describe a simple chemical test that you could use to distinguish the following compounds. You
are to include reagents and conditions, observations and a balanced equation(s) in each case.
OH
(i)
H
C
and
(ii)
and
C
O
CH3
CH2OH
[ACJC / III / Q1 d ]
3 Concentrated sulfuric acid reacts with many organic compounds, forming water as one of the
products. Three examples are shown below.
Concentrated sulfuric acid dehydrates methanoic acid to form a gas, A, with the same
molar mass as ethene.
Concentrated sulfuric acid dehydrates sucrose, C12H22O11, to form a black solid, B.
Concentrated sulfuric acid dehydrates ethane-1,2-diol to form a compound C with a molar
mass of 88 g mol1. In this reaction, 2 moles of ethane-1,2-diol produce 1 mole of C and 2
moles of H2O.
Suggest the identities of A, B and C. Write equations for each reaction and deduce the
structural formula of C.
[HCI / III / Q1f ]
For each of the following pairs of compounds, suggest methods of not more than two steps, by
which they can be distinguished from each other. State the reagents and conditions clearly and
describe what you would see.
Hydroxy Compounds
(i)
and
(ii)
[IJC / III / Q3 e ]
and
Given that the product E is not chiral, suggest a possible structure of E. And hence, deduce the
structure of C8H12O4.
(ii) F is another possible product from step I. However, F contains a chiral centre and it forms a
polymer in step II.
Suggest a possible structure of F and explain why F does not form the same type of product as
E in step II when it is treated with concentrated sulphuric acid.
[NJC / III / Q2 a ii, iii ]
6
Suggest one simple chemical test which would enable you to distinguish the following pairs of
compounds. State reagent(s) and condition(s) and their corresponding observations.
CH3
H3C-HC=CH-CH2-C H3
(CH3)2C=CH-C-CH3
OH
OH
compound C
compound D
[TPJC / III / Q3 a ii ]
8 Joseph Priestly prepared hydrogen chloride in 1772 and found that the compound was a
colourless gas at room temperature. It formed white fumes of hydrochloric acid upon contact
with atmospheric humidity. Hydrogen chloride gas as well as hydrochloric acid are important in
technology and industry.
Hydroxy Compounds
When phenol is added to aqueous sodium hydrogencarbonate, there is no evolution of gas, but
a colourless gas is evolved when 2,4,6-trinitrophenol is used instead. Explain the above
observation as fully as possible, writing a balanced equation for the reaction that occurred.
[YJC / III / Q4 c ii ]
5. Carbonyl
Carbonyl Compounds
1 Oxidation of an alkene Y gives a diol; further oxidation gives a diketone. Which one of the
following could be Y?
A CH3CH=CH2
B CH3CH=CHCH3
C CH3CH=C(CH3)2
D (CH3)2C=C(CH3)2
[AJC / MCQ / Q21]
2 Oestrone, a sex hormone, has the following structural formula.
4 Citronellol is a colourless oily liquid having a rose-like odour. It is the active ingredient in over
30 essential oils and is a major component in perfumes, cosmetics and soaps. It may be
prepared synthetically from compound W using reagent X.
Carbonyl Compounds
Methyl isocyanate, CH3-N=C=O, readily reacts with nucleophiles. By analogy with the
chemistry of other carbonyl compounds, predict which atom will be attacked by a nucleophile.
A carbon atom of the isocyanate group
B carbon atom of the methyl group
C nitrogen atom
D oxygen atom
[SRJC / MCQ / Q27]
Carbonyl Compounds
7 The mechanism below shows how butanone reacts with hydrogen cyanide.
Carbonyl Compounds
Pentan-2-one is treated with cold hydrogen cyanide in the presence of traces of sodium
cyanide. The product X of this reaction is then boiled with hydrochloric acid to give Y. What
are X and Y likely to be?
A
H OH H
H3C C C C CH3
H CN H
H H H OH
H3 C C C C C H
H H H CN
H OH
H CN
H H
H3 C C C
H H
H3C C C
CH3
H COOH H
H H H OH
H 3C C C C C H
H H H COOH
H OH
H3C C C CH3
D
H OH
H3C C C CH3
H COOH
OH
C CH3
CN
H H
H3 C C C
H H
OH
C CH3
COOH
10 Which of the following reagents will give similar results for both butanal and butanone?
A Aqueous alkaline iodine
B Fehlings solution
C Acidified aqueous potassium dichromate(VI) D 2,4-dinitrophenylhydrazine
[AJC H1 / MCQ / Q25]
11 Compound B will show a positive test with all of the
following reagents except
A PBr3, reflux
B 2,4-dinitrophenylhydrazine, warm
C Acidified KMnO4, reflux
D Na, room temperature
[IJC H1 / MCQ / Q24]
12 The first stage in the synthesis of antipyrine, a drug used in reducing fever, is the
Carbonyl Compounds
NHNH2
NHCOCH2COCH3
NHCH2CO2CH2CH3
C
D
CH3COCH2CO
NH N
NHNH2
C
CH2CO2CH2CH3
CH3
14 Which of the following reagents will cause a colour change when the reagent is added to
compound P?
A warm, alkaline aqueous iodine
B 2,4-dinitrophenylhydrazine
C hot, acidified KMnO4
D Fehlings reagent
NYJC H1 / MCQ / Q21]
15 Limonene, A, occurs in oil of lemons and is used to flavour some citrus drinks.
Which of the following is true about limonene?
A It exhibits geometric isomerism.
B Upon reaction with hot acidified potassium manganate (VII), the product
forms an orange precipitate with 2,4-dinitrophenylhydrazine.
C It reacts with bromine dissolved in an inert solvent to form a compound
with the molecular formula C10H16Br2.
D It reacts completely with 1 mole of hydrogen in the presence of a nickel
catalyst to yield a saturated compound.
[MJC H1 / MCQ / Q19]
16 Which reagent gives the same visible result with propanal and with propan-2-ol?
Carbonyl Compounds
A Fehlings reagent
C acidified potassium manganate (VII)
A
B
C
D
2,4-DNPH
Tollens'
Fehling's
negative
positive
positive
positive
negative
negative
positive
positive
negative
negative
negative
positive
18 Compound Q was subjected to the following tests and the results are recorded below. Which of
the following could be compound Q?
Reagent and conditions
observations
Acidified KMnO4, warm
Solution turns from purple to colourless. CO2 is
evolved.
Fehlings reagent, warm
No precipitate seen.
Tollens reagent, warm
Silver mirror observed.
A
Acidified
K2Cr2O7
Tollens
reagent
C3H7Br
X
Y
Z + silver mirror
What could be the formulae for X, Y and Z?
X
Y
Z
A CH3CH2CH2OH
CH3CH2CO2H
CH3CH2CHO
B CH3CH2CH2OH
CH3CH(OH)CH2OH
CH3CO2H
C CH3CH2CH2OH
CH3CH2CHO
CH3CH2CO2H
D CH3CH(OH)CH3
CH3COCH3
CH3CO2H
[MI H1 / MCQ / Q15]
[NYJC H1 / MCQ / Q20]
Carbonyl Compounds
20 How many structural isomers with the molecular formula C 4H8O can reduce Tollens reagent
to form a silver mirror?
A 1
B 2
C 3
D 4
[YJC H1 / MCQ / Q24]
21 An organic compound G is refluxed with acidified potassium manganate (VII) to produce 2
organic compounds H, I and an odourless gas. H gave negative results with Fehlings reagent
but gave a pale yellow precipitate with iodine in an alkaline solution. Effervescence was
observed when I was treated with aqueous sodium carbonate. Both H and I were found to yield
orange crystals when treated with 2,4-dinitrophenylhydrazine.
What is the structure of G?
A
D
[MJC H1 / MCQ / Q20]
22 The table shows the observations of the chemical tests conducted on compound U.
Chemical test
Observations
Warm with 2,4-dinitrophenylhydrazine Orange precipitate
Warm with Tollens reagent
Silver mirror
Warm with alkaline aqueous iodine
Yellow precipitate
From the observations of the chemical tests, what could U be?
A CH3CHO
B CH3COCH3
C CH3CH2CHO
D CH3CH(OH)CH3
[NYJC H1 / MCQ / Q22]
D
[NJC / MCQ / Q21]
[NJC H1 / MCQ / Q25]
Carbonyl Compounds
24 When an alcohol, H, is treated with hot acidified aqueous potassium manganate(VII), the final
oxidation product gives a positive tri-iodomethane test. Which of the following compounds
could correspond to H?
A C6H5CH2OH
B C2H5OH
C CH3CH(OH)C2H5
D C6H5CH(OH)C2H5
[TJC / MCQ / Q21]
25 How many structural isomers with the molecular formula C 4H8O2 (exclude ether) give an
orange precipitate with 2,4-dinitrophenylhydrazine but no precipitate with alkaline aqueous
iodine?
A 3
B 4
C 5
D 6
[VJC / MCQ / Q28]
[VJC H1 / MCQ / Q25]
26 Aldehydes can undergo addition reactions with a variety of compounds of the form HX
according to the following equation.
C
HX
OH
c a t a ly s t
C
H
D
[YJC H2 2011 / Q25]
Carbonyl Compounds
27 The Wittig reaction involves the reaction of a carbonyl compound with a phosphorus ylide to
give an alkene. The reaction occurs because of an important oxaphosphetane intermediate.
Which one of the following structures shows the product of the reaction between the following
compound and the phosphorus ylide shown?
Carbonyl Compounds
For each of the following questions, one or more of the three numbered statements 1 to 3 may
be correct. Decide whether each of the statements is or is not correct. The responses A to D
should be selected on the basis of:
A
B
C
D
1, 2 and 3
are correct
1 only is
correct
Carbonyl Compounds
Which of the following tests can be used to distinguish between the two organic compounds
below?
1 Na metal
2 aqueous bromine
3 acidified KMnO4
7
HO
CH3
OH
HO
oestrone
oestradiol
Which of the following reagents could not be used to distinguish between the two hormones?
1 Fehlings solution
2 I2 in NaOH (aq)
3 Sodium metal
[YJC H1 / MCQ / Q30]
Carbonyl Compounds
Structured Questions
1 Another commonly used oxidising agent for organic reactions is potassium manganate(VII),
KMnO4.
(i) Draw the full structural formula of the organic product that is formed when acidified potassium
manganate(VII) is added separately to compounds A and B.
(ii) Describe a reaction by which you could distinguish between A and B. State the reagents,
conditions and the observations you can make with each compound.
(iii) Compound B reacts with hydrogen cyanide. State the type of reaction and the conditions
necessary for this reaction to take place?
(iv) Draw the structure of the organic product that is formed.
[AJC H1 / IIB / Q5 c, d ]
2 Compound B is a ketone which has the formula C4H8O.
(i) It gives a positive triiodomethane test. Draw the structure of the group present in B.
(ii) Give the structure of the product C obtained in the triiodomethane test.
I2 + NaOH(aq)
B
CHI3 + C
(iii) Deduce the structure of B using the available information from (i) and (ii).
(iv) Describe the use of 2,4-dinitrophenylhydrazine with B.
(v) Compound B can undergo further reaction as shown in the scheme.
B
H2
SOCl2, reflux
Compound X
Compound Y
State how compound Y can be synthesized from Compound X.
Your answer should include the intermediate compound(s) formed in each step and the
reagents and conditions required in each step(s).
[MI H1 / IIB / Q1 b ]
Carbonyl Compounds
(a) Using cinnamaldehyde as the starting material, state suitable reagents and conditions to carry
out the following type of reaction.
(i) addition reaction of the aldehyde group
(ii) oxidation of only the alkene group
(iii) oxidation of only the aldehyde group
For each reaction, draw the structural formula of the organic product.
(b)
(i) Both acetylhydroquinone and vanillin react with 2,4-dinitrophenylhydrazine. Give the
observation expected and write a balanced equation for the reaction of acetylhydroquinone
with 2,4-dinitrophenylhydrazine.
(ii) Describe a simple chemical test each to distinguish acetylhydroquinone from vanillin. State the
reagent and condition, and describe what would be seen with each compound.
[MJC H1 / IIB / Q6 a, b ]
5 Cyclohexanone can be converted to cyclohexanamine, in 3 steps as shown below. Give the
reagents and conditions for steps 1 to 3 and draw the structures for A and B in the boxes
provided.
O
A
Step 1
NH2
Step 3
Step 2
[NYJC / II / Q6 ]
6
Use the information below to identify the compounds F to G. Explain your reasoning.
F and G each has the molecular formula C 4H8O. Both produce an orange precipitate with
2,4-dinitrophenylhydrazine but only F reacts with an alkaline solution of iodine.
[VJC H1 / IIB / Q7 a ii ]
Carbonyl Compounds
Liquid
Molecular formula
C4H6O
Chemical test
Reagent
Results
2,4-dinitrophenylhydrazine
Orange precipitate
Tollens reagent
No reaction
Bromine water
Decolourised
(a) What are the conclusions that can be made about the structure of Z by considering:
(i) test A alone
(ii) test A and B together
(iii) test C alone
(b) Suggest a possible structure of Z.
[YJC H1 / IIA / Q2 a, b]
8
Ibuprofen was discovered by Boots Pharmaceuticals in the late 1960s and was used to treat
arthritis and similar problems. It has now become the third largest selling analgesic after
paracetamol and aspirin. The first step in the manufacturing process is the conversion of 2methyl-1-phenyl-propane, known as IBB (this is short for its common name, isobutylbenzene),
into the compound known as IBAP, shown in the following reaction sequence:
H
CH3
CH3
CH3
+ H3C
CH3
Cl
AlCl3
O
IBB
CH3
IBAP
In the second stage of the industrial synthesis of ibuprofen, IBAP is converted into the
intermediate compound A, whose structural formula is shown below. This then undergoes
H CH3
several further H
reactions
to produce ibuprofen.
CH3
H
CH3
Several steps
H3 C
Compound A
CH3
O
H3 C
OH
Ibuprofen
Carbonyl Compounds
(d) Name the functional group which is present in compound A, but not in IBB or IBAP.
(e) Suggest reagents and conditions that can be used to convert compound A to Ibuprofen in one
step in the laboratory?
(f) Suggest a reason why this method is not used in the actual industrial process to synthesize
Ibuprofen.
(g) Complete the reaction scheme below with compound A as the starting material. Draw the
structural formula of the organic products formed, or give a suitable reagent and conditions (if
any), in each of the boxes provided.
CH3
(i)
CH3
HCN, NaOH(aq); 10
C 20 C
O
H3C
Compound A
Tollens
reagent,
heat
(ii)
(iii)
CH3
CH3
Br
H3C
CH3
Br
O
C
H
CH3
O
H
H3C
or
[YJC H1 / IIA / Q5 ]
Carbonyl Compounds
Essay Questions
1
propanone
ethanoic acid
Mr
58.0
60.0
density/g cm3
0.79
1.05
solubility in water
miscible
fully miscible
(a) Explain the differences in density and solubility in water for propanone and ethanoic acid.
(b) Give a detailed description of the mechanism reaction between propanone and hydrogen
cyanide.
[ACJC / III / Q4 b, c ]
2 Compound P can be synthesised from cinnamaldehyde.
Compound P
cinnamaldehyde
(i) Suggest a synthetic pathway for the formation of Compound P from cinnamaldehyde. Suggest
appropriate reagents and conditions as well as structures of any intermediates formed.
(ii) Give the structural formula of the organic products formed when Compound P is refluxed with
acidified potassium manganite .
(iii) Compound P is able to rotate the plane of polarised light due to the presence of the chiral
carbon atom. Explain why Compound P synthesised from cinnamaldehyde in part (i) does not
exhibit this
behaviour.
[IJC / III / Q2 a ii, iii, iv ]
3 Vanillin and acetylhydroquinone are two
commonly used carbonyl
compound derivatives used in industry. The largest single use of vanillin
is as a flavoring, usually in sweet foods such as ice cream and
chocolate while acetylhydroquinone is used in developing photographic
emulsions. Both compounds exists as yellow solids that are soluble in
water to form a yellow solution which is perceptible even at minute
concentrations.
(a) Both organic compounds react with hydrocyanic acid, HCN at different rates. This reaction
requires an amount of a base such as sodium hydroxide to be added.
(i) Name and describe the mechanism between HCN and acetylhydroquinone. Explain clearly the
role of the base in this reaction.
(ii) In the reaction of vanillin with HCN, only a small amount of a base is required. Suggest why for
acetylhydroquinone, more sodium hydroxide is required for any significant reaction to occur.
(b)
(i) Both vanillin and acetylhydroquinone reacts with 2,4-dinitrophenylhydrazine. Give the
observation expected and write an equation for the reaction with acetylhydroquinone.
Carbonyl Compounds
(ii) Give one positive chemical test each, for vanillin and acetylhydroquinone, which will allow the
two compounds to be distinguished from one another. State the reagents, conditions and
observations expected.
[MJC / III / Q2 a, b ]
4 Three unlabeled reagent bottles are known to be containing three compounds below.
X
Y
Z
O
C
CH2
CH2OH
CH3
CH
OH
OH
O
CH2
(i) Suggest how the identity of the compound in each bottle can be identified by simple chemical
tests. Your answer should state clearly the reagents and conditions used for the test and the
observations of the reactions that allow you to reach your conclusion
(ii)
What type of reaction is undergone when compound X reacts with hydrogen cyanide
and trace amount of NaOH? State the conditions necessary for the reaction to take place.
(iii)
Briefly describe the steps in the mechanism of this reaction.
[NYJC / III / Q4 d ]
5
Chloral hydrate is an unstable drug that can decompose easily to form chloral
with a loss of water molecule. Chloral reacts with cold alkaline hydrogen
cyanide under appropriate conditions to yield compound B.
Chloral hydrate
(i) Draw the displayed formula for compound B.
(ii) Outline the mechanism for the reaction of chloral with hydrogen cyanide.
[TPJC / III / Q4 a ii ]
6
Squaric acid is an unusual organic compound with molecular formula, C 4H2O4, and its systematic name
is 1,2dihydroxycyclobutene-3,4-dione. Suggest what you would expect to see when squaric acid
reacts with :
(a) 2,4-dinitrophenylhydrazine agent
(b) phosphorus pentachloride.
Give equations for the reactions that occurred.
[YJC / III / Q5 a i, c]
Carboxylic Acids
CH3CH2COCl
CH3CH2CN
CH3CH2CN
C6H5CONH2
CH3CO2CH3
CH3CO2CH2CH3
CH3CH2CO2CH3
C6H5NHCOCH3
[AJC / MCQ / Q26]
The diagram below shows the synthesis of Compound S starting from benzene.
Which one of the following gives the correct types of reactions for step 1 to 3?
A
B
C
D
4
5 Which of the following compounds reacts with PCl5 at room temperature to produce an
organic compound that reacts vigorously with water?
A
CH3COOH
B CH3COOCH3
CH3CH2CH2OH
D HOCH2CH2OH
[ACJC / MCQ / Q29]
Carboxylic Acids
D CH3CHO
[NJC H1 / MCQ / Q23]
10 How many moles of H2 react with one mole of the following compound?
A 2
B 3
C 4
D 5
[NJC / MCQ / Q23]
11 Citric acid, which causes the sharp taste of lemon juice, has the following
formula. Which of the following reacts completely with 1 mole of citric acid?
A 3 moles of PCl5
B 3 moles of NaHCO3
C 4 moles of HCl
D 4 moles of NaOH
[PJC H1 / MCQ / Q24]
12 When an organic compound X was treated with phosphorous pentachloride, fumes of HCl
were evolved. When X was warmed with acidified concentrated potassium manganate (VII),
the solution turned colourless from purple.
A CH3CH2CHO
B CH3COCH3
C (CH3)3COH
D C6H5CH=CHCO2H
[TPJC H1 / MCQ / Q18]
13 A compound P reacts with PCl5 to form hydrogen chloride gas and decolourises hot
acidified potassium manganate(VII). Which of the following could P be?
Carboxylic Acids
HO
C
H3C C
C C
H3C C
OH
CH3
O
CH3
H3C C CH3
OH
[YJC / MCQ / Q27]
14 Which one of the following pairs of substances react together to form an organic product that
gives a neutral solution?
A C6H5OH and Na
B C6H5NH2 and HCl
C C6H5CH2CH(NH2)COOH and HCl
D C6H5COCH3 and LiAlH4
[VJC / MCQ / Q26]
15 Which one of the following gives the correct order of acid strength (strongest first) for
propanoic acid, 2-chloropropanoic acid, and 3-chloropropanoic acid?
strongest
CH2ClCH2CO2H
CH3CHClCO2H
CH3CHClCO2H
CH3CH2CO2H
A
B
C
D
CH3CHClCO2H
CH2ClCH2CO2H
CH3CH2CO2H
CH3CHClCO2H
weakest
CH3CH2CO2H
CH3CH2CO2H
CH2ClCH2CO2H
CH2ClCH2CO2H
[ACJC H1 / MCQ / Q25]
C6H5CH2CO2H
C6H5CH2CH2OH
C6H5CH2CH2OH
C6H5CO2H
C6H5OH
C6H5OH
C6H5OH
C6H5CH2CO2H
C6H5CO2H
C6H5CH2CO2H
C6H5CO2H
C6H5OH
C6H5CH2CH2OH
C6H5CO2H
C6H5CH2CO2H
C6H5CH2CH2OH
[NYJC / MCQ / Q27]
X, W, Y, Z
B W, X, Y, Z
Z, Y, W, X
D Z, W, Y, X
[HCI / MCQ / Q30]
Carboxylic Acids
2,4,6-trimethylphenol
When compounds K, L, M and N (not necessarily in that order) are added to separate
portions of water, solutions are formed with pH values of 0.5, 2.5, 3.0 and 3.5.
Deduce which pH value is associated with each of K, L, M and N.
[MJC / MCQ /
Q22]
A
B
C
D
25 Bromine-containing organic compounds can be hydrolysed
under suitable conditions to produce the corresponding
bromide ion, Br-, which then can be reacted with aqueous
Carboxylic Acids
A
B
C
D
[MJC / MCQ / Q24]
26 Which sequence shows the wrong order of increasing ease of hydrolysis?
A C6H5Br < C6H5CH2Cl < CH3CH2COCl < CH3CH2I
B C6H5CH2Cl < C6H5CH2Br < CH3CH2I < CH3CH2COCl
C C6H5Cl < CH3COCH2Cl < C6H5CH2Br < CH3CH2I
D C6H5Br < CH3CH2Cl < C6H5CH2I < CH3CH2COCl
[VJC / MCQ / Q27]
27 Which materials are best used for the synthesis of
the following compound?
A CH3COOH and CH3NH2
B CH3CONH2 and CH3Br
C CH3COCl and CH3NH2
D CH3CONH2 and CH3OH
O
C
H 3C
CH 3
N
H
Carboxylic Acids
Which set of reagents could be used to prepare ethyl butanoate in the laboratory?
A CH3CH2CH2CH2Cl, CH3CO2H, H2SO4
B CH3CH2CH2CH2OH, C2H5Cl, H2SO4
C CH3CH2CH2OH , C2H5CO2H, H2SO4
D CH3CH2CH2CO2H, C2H5OH, H2SO4
[AJC H1 / MCQ / Q23]
31 Which of the following sets of starting materials may be used for the preparation of phenyl
benzoate in the laboratory?
A C6H5OH, C6H5COOH, H2SO4(l)
B C6H5Cl, C6H5COCl
C C6H5OH, C6H5COCl, NaOH(aq)
D C6H5Cl, C6H5COCl, NaOH(aq)
[TPJC / MCQ / Q23]
32 Isopentyl acetate, CH3CO2CH2CH2CH(CH3)2 is prepared by reacting an excess of ethanoic
acid with isopentyl alcohol in the presence of sulfuric acid.
(CH3)2CHCH2CH2OH +
CH3COOH
CH3CO2CH2CH2CH(CH3)2 + H2O
I, II, III
I, II, IV
B
D
II, III, IV
I, II, III, IV
[DHS H2 2011 / Q29]
33 A compound R, with molecular formula C9H10O2, is heated under reflux with aqueous sodium
hydroxide and the resulting mixture then cooled and acidified with dilute sulphuric acid. The
Carboxylic Acids
final products include a compound that turns blue litmus solution red, and another which
gives a purple colouration when tested with aqueous iron(III) chloride. What could R be?
A
C6H5OCOCH2CH3
34 When ethyl ethanoate undergoes hydrolysis with dilute sulphuric acid in the presence of
H218O, a mixture of two products is formed. Which of the following pairs correctly gives the
structures of the two products?
A CH3CO18OH and CH3CH218OH
B CH3COOH and CH3CH218OH
C CH3C18OOH and CH3CH2OH
D CH3CO18OH and CH3CH2OH
[NYJC H1 / MCQ / Q23]
35 Which of the following substances will yield an alcohol upon being heated under reflux with
aqueous sodium hydroxide?
A CH3CH2NH2
B CH3CH2CO2CH3
C CH3CH=CH3
D C6H5Br
[TJC / MCQ / Q23]
36 Which one of the following is formed when the compound V is refluxed with an excess of
aqueous alkali?
A
B
compound V
C6H5CO and OC6H4CO
C
C6H5O and OC6H4CO2
C6H5CO and HOC6H4CO2H
D
C6H5OH and HO2CC6H4CN
[IJC 2011 / MCQ / Q28]
HO
HO2C
C
D
CH3OCO
OCOCH3
is heated
OH
and CH3CO2H
CO2H
HO
and CH3OH
CO2H
CH3CH2OH ,
CH3OH,
HO2C
and HCO2H
OH
and CH3CO2H
[SRJC H1 / MCQ / Q24]
Carboxylic Acids
38 Compound Y is boiled with aqueous sodium hydroxide and the resulting mixture cooled and
acidified with dilute sulphuric acid. The final products include a compound C 3H6O2 and an
alcohol. This alcohol gives a positive iodoform test. What is the formula for compound Y?
A CH3CH2CO2CH3
B CH3CH2 OCOCH3
C CH3CH2CO2CH2CH3
D HOCH2CH2 CO2CH2CH3
[TPJC / MCQ / Q24]
39 Which of the following statements is correct with regards to the conversion of compound B
to compound D?
D
[MJC / MCQ / Q28]
Carboxylic Acids
For each of the following questions, one or more of the three numbered statements 1 to 3 may
be correct. Decide whether each of the statements is or is not correct. The responses A to D
should be selected on the basis of:
A
B
C
D
1, 2 and 3
are correct
1 only is
correct
1 In which of the following two-stage syntheses could a nitrile be the intermediate (X, Y or Z) ?
1 CH3CH2CH2Br X CH3CH2CH2COOH
2 CH3CH2CH2CH2OH Y CH3CH2CH2CH2CH2OH
3 CH3CH2I Z CH3CH2NH2
[NYJC / MCQ / Q37]
2 Which of the reagent/s added will produce similar observation when added to these two
compounds?
1 PCl5
Na
3 Which of the following statements is/are true for HOCH2CO2H and H2NCH2CO2H?
1 Both react with aqueous sodium hydroxide.
2 Both form zwitterions.
3 Both are insoluble in water.
[TJC / MCQ / Q37]
4
Malic acid, HO2CCH(OH)CH2CO2H, is found in some fruits. Which properties does malic
acid have?
1 Its molecule contains a primary alcohol group.
2 It can form esters with both ethanoic acid and with ethanol.
3 1 mole of malic acid will react completely with 3 moles of sodium metal.
[TJC H1 / MCQ / Q30]
Carboxylic Acids
In which of the following pairs is the Ka of the first compound greater than the Ka of the
second compound?
1
2
3
and CH3CH2COOH
CH3CH2CH2COOH and CH3CH2COOH
[SRJC H1 / MCQ / Q30]
Which of the following correctly lists the compounds in order of decreasing acidity?
1
COOH
NO2
OH
3
OH
OH
CH3
OH
OH
Cl
OH
OH
OH
[SRJC / MCQ / Q39]
An unknown compound is refluxed with aqueous sodium hydroxide solution. The product is
acidified with nitric acid and aqueous silver nitrate solution is added. A precipitate is
observed. Which of the following could be the compound?
1 CH3CH2COCl
2 CH2BrCO2H
3 CH3I
[TJC H1 / MCQ / Q29]
9 Which of the following will yield an organic compound containing deuterium? (D = 2H)
1
2
3
Carboxylic Acids
11
12 Which of the following statements are true for the compound below?
1 It is a non-planar compound.
2 When boiled with aqueous sodium hydroxide, it is converted to
Carboxylic Acids
Structured Questions
1
(a)
(b)
(c)
Tartrate ion is the conjugate base of the organic acid tartaric acid, that is used in
vinegar.
(i) When tartaric acid is heated in the presence of hot concentrated sulphuric
acid, two different organic products A and B of molecular formula C4H2O4
and C8H8O10 are formed.
Suggest the structural formula for products A and B.
2
(ii) State and describe the two types of hybridisation present in the C atom of the tartaric acid
molecule.
[MJC / II / Q3 d iv ]
3 Suggest a chemical test to distinguish between the
following pairs of organic compounds.
[NJC / II / Q3 c i ]
4 Methanol can be oxidized to methanoic acid.
(i) Write an equation for the oxidation of methanol to form methanoic acid.
(ii) Describe and explain how the acidities of methanol, methanoic acid and chloromethanoic
acid compare with each other.
[NYJC / II / Q3 b ]
5
Paracetamol is the active drug ingredient used to relieve headache, fever and flu. It was first
synthesised from 4-nitrophenol by Harmon Northrop Morse in 1878 and was commercially
produced and marketed in 1955. The structure of paracetamol is given below:
(a) Suggest a pathway to synthesise paracetamol from 4-nitrophenol .
Two other common drugs used to relieve headache, fever and flu are
aspirin and pseudoephedrine. The structural formulae, molar masses and
melting points of paracetamol, aspirin and 4-nitrophenol are given below.
Carboxylic Acids
(b) Suggest a reason for the lower melting point of aspirin as compared to 4-nitrophenol.
(c) Describe one simple test-tube reaction you could use to distinguish aspirin from
pseudoephedrine. State the reagents conditions and observations that can be seen.
[PJC / II / Q7 a, d, e ]
6 Compound Y can be synthesized from ethene in a 2-step process as follows:
I
CH2=CH2
II
X
O
C
O
OCH2 CH2 O
Y
(i) Suggest reagents and conditions for steps I and II.
(ii) Draw the displayed formula for the intermediate X.
[SRJC H1 / IIB / Q3 b ]
7
Lidocaine is a common local anesthetic drug used topically to relieve itching, burning and
pain from skin inflammations.
Using simple molecules like 2,6-dimethylphenylamine, ammonia and chloroethane,
lidocaine can be synthesized as shown below.
(i) Draw the structures of W and Z in the boxes below.
(ii) Suggest the structure of lidocaine.
(iii) Do you foresee any problem in the synthesis of Z? If yes, explain why.
CH3
CH3
NHCOCH2Cl
NH2
+
CH3
Y+Z
heat in a sealed
tube to give
lidocaine
NH3
+ CH3CH2Cl
heat in a
sealed tube
Z (C4NH11)
CH3
[TJC / II / Q5 c ]
0.025 mol of a hydrocarbon X was combusted completely to produce 4.4 g of carbon dioxide
gas and 1.35 g of water.
1 mol of X can react with 2 mol of hydrogen gas. When X reacted with acidified potassium
manganate(VII), the latter was decolourised and compound Y, C2H2O4, was formed as one
of its products. Y reacted with Na2CO3 to give a colourless, odourless and acidic gas. Y
reacted with 2 mol of CH3OH under suitable conditions to form Z, C4H6O4.
Determine the molecular formula of the hydrocarbon X, suggest and explain how you arrive
at the structures for X, Y and Z.
Carboxylic Acids
[TJC H1 / IIB / Q6 d ]
9
CH3CH2CO2H CH3CH2CH2OH
CH3CHCO2H
Cl
Arrange the above three compounds in increasing order of acidity and explain your answer.
[TJC H1 / IIB / Q7 a iii ]
10 Ferulic acid, which can be used as antioxidant, is found in seeds CH3O
of plants such as wheat and rice. It has the structure as shown:
State what you would observe and give the structural formula of
HO
the organic product when ferulic acid reacts with the following
reagents: Aqueous bromine, Ethanoyl chloride, Hot acidified
potassium manganate(VII)
COOH
State what you would observe and give the structural formula of the organic product when
ferulic acid reacts with the following reagents: PCl5
[TPJC / II / Q8 a ]
11 Use the information below to identify the compounds H to I. Explain your reasoning.
H and I each has the molecular formula C 2H4O2. H has an acrid (sharp) smell whereas I
has a fruity aroma. H reacts instantaneously with cold aqueous sodium hydroxide but I
reacts only when heated under reflux with aqueous alkali.
[VJC H1 / IIB / Q7 a iii ]
CH3O
COOH
12 Ferulic acid is an active ingredient in the Chinese herb Danggui.
Its structure is given below. [The CH3O group can be considered
relatively inert]
HO
(a) Ferulic acid exists as a pair of geometric isomers. Draw diagrams
to illustrate these isomers
(b) When gaseous hydrogen chloride is reacted with Ferulic acid, the products exhibit a different
type of stereoisomerism.
(i) Name and define the new type of stereoisomerism exhibited.
(ii) Draw diagrams to illustrate the isomerism you have described in (i).
(c) Ferulic acid is observed to be relatively soluble in water.
(i) Explain its solubility in water with the aid of a diagram.
(ii) Will Ferulic acid be more or less soluble in aqueous sodium hydroxide? Give your
reasoning.
(d) Draw the structures of the organic products formed when Ferulic acid reacts with the
following reagents:
(i) Aqueous bromine
(ii) Cold dilute manganate(VII) ions
(iii) Hot acidified manganate(VII) ions
(iv)Lithium aluminium hydride
(v) Benzoyl chloride
(vi) Thionyl chloride, SOCl2
[YJC / II / Q4 ]
Carboxylic Acids
Essay Questions
1
(i) Explain the differences in Ka values between the 3 compounds shown below.
Na2CO3 can be also be used to distinguish between carboxylic acids and alcohols. However,
this is not possible for propanoic acid and 2-hydroxypropanoic acid since both are carboxylic
acids.
(i) The melting points of propanoic acid and 2-hydroxypropanoic acid are 21 oC and 53 oC
respectively. Explain the difference in the melting points of these two acids.
(ii) Suggest chemical reagents and the conditions to distinguish both the monobasic acids.
Describe your observations for both the acids.
[PJC / III / Q2 c ]
3
(a) 7.8 g of ethanal reacts with 5.0 g of hydrogen cyanide in the presence of a trace amount of
sodium cyanide at 10 20 C to give 12.0 g of 2-hydroxypropanenitrile.
(i) Calculate the percentage yield of 2-hydroxypropanenitrile in this reaction.
(ii) Explain why 2-hydroxypropanenitrile has no effect on polarised light even though it contains
a chiral carbon.
(iii) -Hydroxy acids (AHAs) are naturally occurring carboxylic acids which are well-known for
their use in the cosmetic industry. Lactic acid, HOCH(CH 3)COOH, is an AHA can be formed
from 2-hydroxypropanenitrile. Write a balanced equation for this reaction, stating clearly the
reagents and conditions.
(b) Suggest methods by which the following compounds could be distinguished from each other
by chemical tests.
(i)
NHCOCH2
Br
and
OCOCH2
Cl
(ii)
and
(c) State and explain the relative solubility of 2-aminobenzoic acid and 4-aminobenzoic acid in
water.
Carboxylic Acids
NH2
H2N
COOH
2-aminobenzoic acid
4(a)
COOH
4-aminobenzoic acid
[SRJC / III / Q4 ]
A lethal combination of the following three prescriptive drugs simultaneously can cause
death. They are chloral hydrate, acetaminophen and meprobamate. The structures of
these three drugs are as shown:
Cl
Cl
OH
Cl
H
N
O
HO
acetaminophen
chloral hydrate
O
O
H2N
CH3
OH
NH2
meprobamate
Suggest chemical tests to identify two of the above drugs (namely acetaminophen and
meprobamate). You must give a positive test for each drug stating observations as well
as essential reagents and conditions.
(b)
CH2OH
A
HO
HO
PCl5
B
HO
CONHCH2CH2
OH
Carboxylic Acids
(iii) Suggest a reagent together with the condition, which can be used to modify the chemical
structure of compound D, to make it water soluble.
[TPJC / III / Q4 a i, b ]
5
Compound A can absorb ultraviolet rays and is used in the production of skin cream. Its
structural formula is shown below:
O
CH3O
CH
CH
1. NaOH
HO
CHO
2. CH3I
Compound A
CH3O
CH2(CH2)3CH3
CHO
Step I
Step II
CH3O
Compound A
CH=CHCOOH
Step III
State the reagents and conditions for the reaction in Step III.
Suggest the mechanism of Step I.
[YJC / III / Q3 c iii ]
6
Compound X has the molecular formula C 4H6O2. X reacts with hydrogen cyanide to form Y,
C6H8O2N2. X also reacts with hot acidified potassium dichromate(VI) solution to produce Z,
C4H6O3. 2.50 g of Z (Mr = 102) was dissolved in 250 cm 3 of water. 25.0 cm3 of the solution
required 24.50 cm3 of 0.100 mol dm-3 of sodium hydroxide for complete neutralisation.
(i) Calculate the number of moles of Z that will be neutralised by one mole of sodium
hydroxide. Hence suggest one structural formula of X. Identify compounds Y and Z.
(ii) Draw one isomer of X that behaves like X. Label the isomer W.
(iii) Suggest one simple chemical test that can used to distinguish X from W. State the reagents,
reaction conditions and observations.
[YJC / III / Q5 d]
Nitrogen Compounds
7. Nitrogen
1 A nitrile X undergoes the following two reactions:
What would be produced when the products from the two reactions are mixed together?
A [ CH3CH2NH3+ ] [ O2CCH3 ]
B [ CH3CH2NH3+ ] [ O2CCH2CH3 ]
C CH3CONHCH2CH3
D CH3CH2CONHCH2CH3
[AJC / MCQ / Q28]
2
3 With what reagent would phenylamine and phenol give a similar reaction?
A Br2
B HCl (aq)
C Na metal
D NaOH (aq)
[MI / MCQ / Q28]
4 Aspartame is a sweetener commonly used in diet soft drinks and is provided as a table
condiment.
Aspartame
What are produced when aspartame is heated with aqueous sulphuric acid?
A
B
Nitrogen Compounds
When aqueous bromine is added to a solution of phenylamine, the colour of the bromine
disappears. Which of the following statements is true?
A
B
C
D
Step 1
Dilute H2SO4, K2Cr2O7,
heat
Concentrated HNO3,
Concentrated H2SO4,
heat
Concentrated HNO3,
Concentrated H2SO4,
heat
Step 2
Concentrated HNO3,
Concentrated H2SO4,
heat
Concentrated HNO3,
Concentrated H2SO4,
heat
Dilute H2SO4, KMnO4,
heat
Step 3
Concentrated HCl, Sn,
heat
Nitrogen Compounds
skin disorders, and can also be used in the treatment of irritable bowel syndrome.
H2N
COOH
PABA
Which of the following is a possible means of its preparation?
A
CN
CN
CH3
CH3
conc HNO3
conc H2SO4
H2O / H+
H2O / H+
heat
conc HNO3
heat
conc H2SO4
conc HNO3
conc H2SO4
KMnO4 / H+
heat
KMnO4 / H+
conc HNO3
heat
conc H2SO4
Consider the aromatic amine, phenylamine. Which of the following statement is true?
A It undergoes electrophilic addition
B It is more basic than ethylamine
C It gives no reaction with ethanoyl chloride
D It reacts with aqueous bromine to give a white precipitate
[YJC / MCQ / Q29]
9 Four students suggested reagents that can differentiate the following two compounds.
thionyl chloride
bromine water
sodium carbonate
[VJC H2 2011 / Q25]
Nitrogen Compounds
10 Which one of the following shows the given ions arranged in order of increasing pKa values?
A
B
C
D
B III, II, I, IV
D I, III, II, IV
[TJC / MCQ / Q28]
12 Which of the following statements explains why C6H5NH2 is a weaker base than CH3NH2?
A C6H5NH2 is less volatile than CH3NH2.
B The methyl group in CH3NH2 is electron withdrawing, hence stablising the ion formed on
dissociation.
C The electron rich C6H5 group in C6H5NH2 is electron releasing.
D The lone pair of electrons on the nitrogen in C6H5NH2 is delocalized over the benzene
ring.
[TPJC / MCQ / Q29]
13 Which sequence shows the nitrogen compounds in increasing order of basic strength?
least basic
most basic
C
D
[AJC / MCQ / Q29]
14 Why do proteins have a buffering effect in cells?
A They are non-polar.
B They are amphoteric.
C They form colloidal solutions.
D They are a major component of cell surface membranes.
Nitrogen Compounds
15 Amino acids have comparatively high melting points when compared with other organic
compounds of similar mass. Which of the following statements best explains this
observation?
A In the solid state, amino acids are held together by strong hydrogen bonds.
B In order to melt an amino acid, strong covalent bonds are broken.
C Amino acids are held together by ionic bonding.
D Amino acids are held in fixed positions in a solid lattice.
[HCI / MCQ / Q27]
16 Which statement is false about an -amino acid?
A
It exists as a solid with high melting point.
B
The amino group and carboxylic acid group are attached to the same carbon.
C
They may exhibit optical isomerism.
D
It can behave as a strong acid or base, and is thus amphoteric.
[MI H2 2011 / Q29]
17 The structures of some amino acids are shown below:
H
H2N
COOH
H2N
COOH
(CH2)4
(CH2)2
NH2
COOH
glutamic acid
lysine
H
H 2N
COOH
H2N
COOH
CH
H3C
phenylalanine
CH3
valine
Which of the following pairs of amino acids are likely to be found on the exterior of a
globular protein?
A glutamic acid and lysine
C
glutamic acid and valine
B valine and phenylalanine
D
lysine and phenylalanine
[IJC H2 2011 / Q30]
Nitrogen Compounds
18 Tyrosine is one of the 20 amino acids that is used by cells to synthesise proteins, and
was first discovered in cheese.
O
OH
HO
NH2
Tyrosine
D
[AJC / MCQ / Q30]
D
[IJC / MCQ / Q13]
21 The pKa values of C1 carboxyl group, C2 carboxyl group, and amino group of aspartic
Nitrogen Compounds
acid are 1.88, 3.65, and 9.60, respectively. Its structure is as shown below:
O
HO
C1
C2
O
OH
NH2
C1
C2
O
C1
O
HO
NH3
NH3
D
OH
O
O
C2
C1
C2
NH2
C
HO
O
-
C1
C2
NH3
HN
O
N
H
O
OH
HO
OH
NH2
NH2
OH
OH
HO
NH2
OH
NH2
Nitrogen Compounds
23
The amino acids, glutamic acid and glutamine, can react with each other to formamide
linkages.
What is the maximum number of different compounds, each containing one natural
amide linkage that can be formed from one molecule of glutamine and one molecule of
glutamic acid?
A 2
B
3
C
4
D
5
[ACJC H2 2011 / Q22]
24 Aspartame is widely used as a sweetener in canned drinks.
H2N
CH CONHCH CO2CH3
HO2CCH2
CH2
Aspartame
When Aspartame is treated with LiAlH4 in dry ether, what is the final product obtained?
A
H2N
CH CH2NHCH CH2OH
HOCH2CH2
CH2
H2N
CH CONHCH CH2OH
HOCH2CH2
CH2
H2N
CH CH2NHCH CO2CH3
HO2CCH2
CH2
H2N
CH CONHCH CH2OH
HO2C CH2
CH2
Nitrogen Compounds
25 Gastrins are heptadecapeptide (17 amino acid units) hormones that stimulate the secretion
of gastric acid in the stomach of mammals. On hydrolysis of gastrins, the following 4 peptide
fragments were isolated.
gly-trp,
leu-glu-glu-glu-glu-ala-ala-try,
glu-gly-pro-trp,
met-asp-phe
C-terminus analysis of the heptatdecapeptide yields a phe residue while N-terminus analysis
yields a glu residue. Based on the information above, suggest a primary structure for the
heptatdecapeptide and the number of peptide bonds it contains.
A
B
C
D
[MJC / MCQ / Q19]
26 Partial hydrolysis of a decapeptide (containing 10 amino acid residues) using an enzyme
yielded the following tripeptide fragments:
HisTyrArg,
TyrArgThr,
GlnThrAsp,
AspArgHis,
ArgHisTyr,
ThrArgGln
asp-pro-tyr-leu-ala-leu-tyr-asp-pro-gly
asp-pro-gly-asp-pro-tyr-leu-leu-tyr-ala
gly-asp-pro-asp-pro-tyr-ala-tyr-leu-leu
ala-asp-pro-gly-asp-pro-tyr-leu-leu-tyr
[SRJC H2 2011 / Q30]
Nitrogen Compounds
A
B
C
D
29 The following diagram shows the structural components of oxyhaemoglobin, the oxygenated
form of haemoglobin,
30 Which of the following proteins will not retain its primary structure?
A
B
C
D
Nitrogen Compounds
For each of the following questions, one or more of the three numbered statements 1 to 3 may
be correct. Decide whether each of the statements is or is not correct. The responses A to D
should be selected on the basis of:
A
B
C
D
1, 2 and 3
are correct
1
1 only is
correct
The structure below shows part of a protein. What type of interactions involving the side
chains of the above protein segment could be responsible for the maintenance of the
tertiary structure of the protein?
What would be formed by prolonged boiling of Karbutilate with aqueous sodium hydroxide?
1
2
3 H2NC(CH3)3
Nitrogen Compounds
Polyacrylonitrile is a polymer used in making carpets and upholstery. The structure of the
monomer of polyacrylonotrile is shown below.
Monomer of polyacrylonotrile
Which of the following compounds is/are obtained when the polypeptide is hydrolysed?
1
2
3
[IJC / MCQ / Q40]
6 Which of the following statements regarding the denaturation of a protein is true?
1 The flavour and texture of foods may be affected.
2 Renaturation is possible if the denatured protein precipitates out.
3 The amino acid sequence is altered.
[NJC / MCQ / Q38]
7 Precipitation is widely used in downstream processing of biological products, such as
proteins. For example, in the biotechnology industry, protein precipitation is used to eliminate
contaminants commonly contained in blood. Which of the following reagents can be used to
induce protein precipitation?
1 0.1 mol dm-3 aqueous sodium hydroxide
2 a saturated aqueous solution of (NH4)2SO4
3 0.1 mol dm-3 Pb(NO3)2
[IJC / MCQ / Q38]
8
Nitrogen Compounds
R group interactions are needed to hold the tertiary structure of a protein in its necessary
shape. Identify which type of R group interaction is destroyed by extreme pH changes when
a protein is denatured. Explain in chemical terms how this R group interaction is destroyed.
[AJC / II / Q5d ]
2 The enzyme phospholipase A2, from rattlesnake venom, is a biological catalyst used in the
hydrolysis of phospholipids as shown below.
Nitrogen Compounds
Suggest how the tertiary structure of the phospholipase A2 may be affected if all the
phenylalanine in the enzyme are replaced by serine, and explain why this might prevent the
enzyme from working.
[HCI / II / Q5 a, b, c ]
3 (a) The structural formulae of three amino acids are given below.
(i) Which amino acid when dissolved in water shows basic character?
Explain your answer.
(ii) Draw structural formulae for the dipeptides that can be formed between lysine and
serine.
(iii) Crystals of the simplest amino acid, glycine, NH 2CH2CO2H melt between 230oC to
235oC. Suggest why the melting point of glycine is higher than that of
hydroxyethanoic acid, HOCH2CO2H (m.p. 75-80oC).
(b) Partial hydrolysis of a tetrapeptide produces the following three dipeptides, as well as the
individual amino acids.
NH2CH(CH2CH2CH3)CONHCH(CH2CH2CH3)COOH
H2NCH(CH3)CONHCH(CH2CH2CH3)COOH
NH2CH(CH2CH2CH3)CONHCH(CH2Ph)COOH
Deduce the order in which the amino acids are bonded in the tetrapeptide, showing your
reasoning.
[IJC / II / Q9 b, c ]
4 Much research has been done in recent years investigating the exact nature of Spider silk.
The silk of a spiders web is at least five times as strong as steel. This can be attributed to
the secondary structure of proteins , specifically the pleated sheet.
(a) Draw a diagram, with displayed formula; showing two strands of a pleated sheet
structure of the protein, the formula of which is given below. Indicate clearly on the diagram
any type of interactions present between the two strands.
CHRNHCOCHRNHCOCHRNHCO
(b) Name another type of secondary structure that is predominant in DNA and briefly explain its
structure.
(c) A silk fibre is composed of many identical protein chains, which are made from the aminoacids such as glycine, glutamine and serine.
glycine
glutamine
serine
(i) Draw the zwitterionic structure of glutamine and account for the high solubility of the aminoacid in water.
Nitrogen Compounds
(ii) Amino acids can act as acids or bases. Write an equation to show the reaction between
serine and aqueous sodium carbonate.
(iii) Draw the structural formula of a tripeptide with the sequence gly-gln-ser, showing the
form which it would exist at pH 3.
(d) In a laboratory setting, hydrolysis of a small portion of Spider silk comprising of a
pentapeptide portion comprising of the 3 amino-acids stated in (c), produced the following
smaller tripeptide fragments.
NH2CH(CH2OH)CONHCH2CONHCH(CH2OH)COOH
NH2CH(CH2CH2CONH2)CONHCH(CH2OH)CONHCH2COOH
NH2CH2CONHCH(CH2OH)CONHCH(CH2CH2CONH2)COOH
(i) Suggest suitable reagents and conditions for the hydrolysis reaction.
(ii) Suggest a possible sequence for the primary structure of the pentapeptide portion of the
Spider silk.
(e) The Mr of a silk protein molecule is about 610,000. Assuming it is only made from glycine,
glutamine and serine in the proportion of 2 : 1 : 3 respectively, calculate the average number
of amino-acid residues in the protein chain.
[ Mr (glycine) = 75; Mr (glutamine) = 146; Mr (serine) = 105 ]
[MJC / II / Q5 ]
5 (a) The graph below shows the effect of temperature on the -helix structure of a polypeptide
chain found in a protein.
(i) In what level of protein structure is the -helix structure commonly found?
(ii) Name an example of a protein that is entirely made up of the -helix structure.
(iii) What type of bond helps to maintain the -helix structure?
(iv) Explain what happens to the -helix structure in proteins at a temperature above 60 oC.
(b)
(i) State the function of haemoglobin in the body, and state how it carries out this function.
(ii) In some illnesses, it is necessary to increase the rate of oxyhaemoglobin formation.
Suggest one method in which the rate of oxyhaemoglobin formation can be increased.
Explain your answer.
[NYJC / II / Q7 ]
6
(a) The diagram below shows the structure, at pH 7, of a fragment from a protein which contains
four amino acids, A, B, C, and D.
A
NHCHCONHCHCONHCHCONHCHCO
HOOCCH2
CH2SH
CH
CH3
CH2OH
CH3
(i) Draw the structure of the first amino acid, A, that could be obtained by hydrolysis of the
protein fragment.
Nitrogen Compounds
(ii) Which side-chains in the amino acids A to D are most likely to be involved in the denaturing
of proteins by changes in pH? Explain your answers, giving equation(s) or structure(s)
where possible.
(iii) Show, with diagrams, how the side-chains on amino acids B and D could be involved in the
maintenance of the tertiary structure of the protein.
(b) The white of an egg is about 88% water and 12% globular protein (by mass). When heated,
the egg white undergoes gross conformational changes. What happens to the structure of a
globular protein during these changes?
[TPJC / II / Q9 ]
7(a)
Electrophoresis is a technique used to identify different amino acids. In a particular
electrophoresis experiment, a piece of rectangular filter paper is soaked in an aqueous
solution of pH 3 and three amino acids labelled A, B and C are dotted onto the middle of the
paper. A potential difference is then applied. After a while, the paper is sprayed with a
colouring chemical to locate the amino acids.
A
CH3
CH2NH2
HOOC C CH2COOH
H3C C CH2COOH
H3C C CH2COOH
NH2
CH3
NH2
NH2
Q
(ii) Which of the three amino acids P, Q or R in (i) corresponds to dot B at the end of the
experiment? Briefly explain your reasoning.
(b) Arrange the compounds CH3NH2, (CH3)2NH and CH2BrNH2 in order of increasing base
strength. Explain your answer.
[YJC / II / Q5 c, d ]
Nitrogen Compounds
Essay Questions
1
The table below gives the numerical Kb values of CH3NH2, NH2OH and C6H5NH2. Suggest
reasons for the different Kb values of these compounds.
[MJC / III / Q5 b ]
2
(a)
(i)
(ii)
(b)
Proteins are naturally occurring polypeptides of relative molecular mass greater than 5000
and are essential for life in all living things and have many biological functions in our bodies.
The protein molecules are large and are responsible for growth, repair and maintenance of
the body. The building blocks of proteins are amino acids, such as leucine and glutamine.
Many proteins contain significant amounts of secondary structures as -helix structures or pleated sheets.
What is meant by the secondary structure of a protein?
Sketch a diagram showing two strands of a -pleated sheet structure, indicating the
essential features on your diagram. You may choose to use the general formula of a primary
structure as shown below.
-CHRNHCOCHRNHCOCHRNHCOThe folding of the -structures in enzymes is caused by the interactions of the R groups.
Give simple examples of four different group interactions, illustrating each case with a
suitable formula for each R group concerned.
[PJC / III / Q1 a, b ]
Nitrogen Compounds
4
(a) Suggest one simple chemical test which would enable you to distinguish the following pairs
of compounds. State reagent(s) and condition(s) and their corresponding observations.
NH2
H2N
CH2CH2CH3
O2N
CHCH2CH3
CH2NH2
(c) Trypsin and chymotrypsin are secreted by the pancreas to aid the digestion of proteins in the
small intestine. In the study of the primary structure of a polypeptide A, the following
fragments were obtained when A was digested using trypsin which cleaves peptide bonds at
the carboxyl end of phenylalanine (phe).
phe,
try-lys-gly-ala,
gly-lys-phe,
ser-lys-ala-phe
When A was digested using chymotrypsin which cleaves at the carboxyl end of lysine (lys),
the following fragments were obtained.
ala-phe-gly-lys,
phe-ser-lys,
gly-ala
phe-try-lys
Deduce the primary structure of A.
[TPJC / III / Q3 a i, b, c ]
5
(a) Explain the meaning of each of the following terms as applied to proteins, illustrating your
answer with one appropriate example:
(i) Denaturation
(ii) Quaternary structure
(b) Aspartame which is used as an artificial sweetener has the following
formula: Aspartame can be prepared through a series of reactions
staring with amino acids.
(i) Give the structural formula of the amino acids that could be used to
prepare aspartame.
(ii)
Describe the types of R group interactions that could exist for these amino acids.
(iii) Describe a simple chemical test by which you could identify one of the functional groups
in Aspartame.
[VJC / III / Q5 a, b ]
6
(a) The diagram below shows part of a protein formed from three amino acids
O H
O H2C
C C N C
H H
H2
C
CH2
H H
N C C N
O CH2SH
(i) Draw the structures of the three amino acids from which this part of the protein is formed.
(ii) Describe with the aid of diagrams if necessary, the secondary and tertiary structures of
protein.
Nitrogen Compounds
(iii) A protein can be denatured by the application of temperature above 40 oC. Explain how
denaturation of proteins occurs.
(b) Describe simple chemical tests (reagents, conditions, observations and equations) to
distinguish between the following pairs of compounds:
CHCH2Cl
CHCH2Cl
Cl
CH2NH2
and
H2N
CH2Cl
[YJC / III / Q4 b, c i ]