ORGANIC WS 107 - AMINES

16

Amides can be made by reacting amines with acyl chlorides, as in the example below.
CH3CH2COCl + H2NCH2CH2CH3 CH3CH2CONHCH2CH2CH3 + HCl
(a) What type of reaction mechanism is this?
......................................................................................................................................[1]
(b) What compound could CH3CH2COCl be made from, and what reagent would you use?
..........................................................................................................................................
......................................................................................................................................[2]
(c) The amine CH3CH2CH2NH2 can be made from CH3CH2Br in two steps.

CH3CH2Br

(i)

II

CH3CH2CH2NH2

Draw the structural formula of the intermediate in the box provided.

...................................................................................................................................

(ii)

State the reagents and conditions for step I.

...................................................................................................................................

(iii)

State the reagents and conditions for step II.

...................................................................................................................................
[4]

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7
7

10
10
Phenylamine is an important intermediate compound for the production of dyes.
Phenylamine is an important intermediate compound for the production of dyes.

For
Examiner's
For
Use
Examiner's
Use

NH2
NH2
phenylamine

phenylamine
(a) Phenylamine can be synthesised from benzene in two steps. Draw the structural formula
of the intermediate
Y in the scheme
below, and
suggest
conditions
for
(a) Phenylamine
can be synthesised
from benzene
in two
steps.reagents
Draw theand
structural
formula
steps
I
and
II.
of the intermediate Y in the scheme below, and suggest reagents and conditions for
steps I and II.

II

II

NH2

NH2

Y
reagent + conditions for step I .........................................................................................

reagent + conditions for step I .........................................................................................

reagent + conditions for step II ........................................................................................
[4]
reagent + conditions for step II ........................................................................................
[4]

(b) Phenylamine is a weak base.

(b) Phenylamine
a weak base.
(i) Write anisequation
showing phenylamine acting as a base.
(i) Write an equation showing phenylamine acting as a base.

(ii) How would you expect its basicity to compare with that of ammonia?

(ii) How would you expect its basicity to compare with that of ammonia?
..................................................................................................................................
(iii) ..................................................................................................................................
Explain the reasoning for your answer in (ii).

(iii) Explain the reasoning for your answer in (ii).

..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[3]
..................................................................................................................................
[3]

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(c) Dyes can be made from phenylamine by first converting it into benzenediazonium
chloride, and then coupling this with a phenol.
III

N2+Cl

NH2

IV
dye
+ a phenol

(i) State the reagents and condition needed for step III.
..................................................................................................................................
(ii) What reagent is the phenol dissolved in for step IV to be effective?
..................................................................................................................................
(iii) Suggest the structural formula of the dye formed when benzenediazonium
chloride is coupled with 2-methylphenol.

[4]
[Total: 11]

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10

3 6

The antipyretic (fever-reducing) drug antifebrin can be made from benzene and ethanoic
acid by the following route.
NO2
I

For
Examiner's
Use

NH2
II
NHCOCH3
IV

CH3CO2H
(a)

III

CH3COCl

antifebrin

(i) What type of reaction is reaction I?

..................................................................................................................................
(ii) Suggest the reagents and conditions for reaction I.
..................................................................................................................................
(iii) Complete the following scheme showing the mechanism of reaction I, by drawing
appropriate formulae in the three boxes.
NO2

[6]
(b)

(i) What type of reaction is reaction II?

..................................................................................................................................
(ii) Suggest the reagents and conditions for reaction II.
..................................................................................................................................
[2]
11

(c) Suggest the reagents and conditions for reaction III.

.................................................................................................................................... [1]
(d)

(i) Apart from the benzene ring, name the functional group in antifebrin.
..................................................................................................................................
(ii) What reagents and conditions are needed to hydrolyse antifebrin?

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[2]
[Total: 11]

For
Examiner's
Use

4 4

Rodinol is used as a photographic developer. In alkaline solution it is a mild reducing agent,

providing electrons according to the following half equation.
OH

2 OH

H2O

NH3

2e
E = +0.65 V

NH2

rodinol
Rodinol develops a latent photographic image by reducing activated silver bromide grains
to silver metal and bromide ions.
(a) Construct a balanced equation for the reaction between rodinol and AgBr.

.................................................................................................................................... [1]
(b) Suggest, with a reason, how the basicity of rodinol might compare to that of ammonia.
..........................................................................................................................................
..........................................................................................................................................
.................................................................................................................................... [2]
(c) Suggest structural formulae for the compounds E, F and G in the following chart of the
reactions of rodinol.

NaOH
OH
E

HCl

G
NH2
rodinol

F
Br2(aq)

[3]
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For
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For
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(d) Rodinol can be synthesised from phenol by the following route.

OH

OH

OH

II

NO2

NH2

(i) Suggest reagents and conditions for step I.

..................................................................................................................................
(ii) What type of reaction is step II?
..................................................................................................................................
(iii) Place a tick in the box by the most suitable reagent for step II.
(place a tick in one box only)
H 3O+ + heat
OH(aq) + heat
Cr2O72 + H+ + heat
HNO3(aq)
Sn + HCl (aq)
NH3 in ethanol + heat/pressure
[3]
(e) Rodinol is also an important intermediate in the commercial production of the
analgesic drug paracetamol.
OH

NH2

OH

NHCOCH3
paracetamol

(i) Name two functional groups in paracetamol.

..................................................................................................................................
..................................................................................................................................
(ii) Suggest a reagent to convert rodinol into paracetamol.
..................................................................................................................................
[3]
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[Total: 12]
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10

5 5

10 used in skin creams for sprains and other

Benzocaine is an important local anaesthetic
muscular
pains. It can be made by the following route.
5
Benzocaine is an important local anaesthetic used in skin creams for sprains and other

For
Examiners
Use
For
Examiners
Use

muscular pains. It can be made by the following route.

CH3

CH3
CH3

CO2H

CH3

CO2H

CO2H

II
I

CO2H

III
II

CO2CH2CH3
CO2CH2CH3

IV
III

NO2

NO2

NO2

NO2

IV

NH2

NH2

NH2

NH2

benzocaine

benzocaine

(a) Suggest reagents and conditions for each of the above four reactions.

(a) Suggest reagents and conditions for each of the above four reactions.

...................................................................................................................................

...................................................................................................................................

II

II...................................................................................................................................
...................................................................................................................................

III

...................................................................................................................................
III
...................................................................................................................................

IV

..............................................................................................................................
IV
.............................................................................................................................. [6]
[6]

(b) Draw
stepssteps
to show
the the
mechanism
of reaction
I. I.
(b) Draw
to show
mechanism
of reaction

[2]

[2]
(c) Another local anaesthetic is amylocaine, which can be made from compound X.

(c) Another local anaesthetic is amylocaine, which can be made from compound X.
O

O
C

CH2

NH2

NH2
CCH2
CH3
CH
CH32CH3

CH2CH3

O
C O
C
O

CH2

CH2

CH3
CHCH
33
2CH

CH3

CH3
CH3

CH3

CH CH

2
3
amylocaine

amylocaine

X
(i)

(i)

Apart from the benzene ring, name two functional groups in the molecule of
Apartcompound
from theX.benzene ring, name two functional groups in the molecule of

compound X.

...................................................................................................................................

...................................................................................................................................
11
...................................................................................................................................
(ii)...................................................................................................................................
Explain whether compound X would be more or less basic than benzocaine.
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9701/04/M/J/06
...................................................................................................................................
[3]

[Total: 11]

For
Examiners
Use

10

65

4-Amino-1-methylbenzene, F, is a useful starting material for making several dyes. The

following chart shows some of its reactions.
Br
CH3
reaction I

NH2
Br

CH3
reaction II
+ CH3COCl
NH2
F

reaction III
+ HCl

H
(a) (i)

Suggest reagents and conditions for reaction I.

...................................................................................................................................

(ii)

Draw the structural formulae of compounds G and H in the boxes above.

(iii)

Name the functional group you have drawn in compound G.

...................................................................................................................................
[4]

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For
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For
Examiners
Use

11
(b) The dye J can be made from F by the following series of reactions.
reaction IV
H3C

H3C

NH2

N2Cl
reaction V

H3C

H3C
N

OH
CH3

Suggest reagents and conditions for

(i)

reaction IV, ................................................................................................................

(ii)

reaction V.
...................................................................................................................................
[4]

(c) Many dyestuffs used as food colourings, such as Sunset Yellow, contain sodium
sulphonate (SO 3Na+) groups attached to the rings. Suggest, with an explanation, a
reason for this.

SO 3 Na+
HO
N
N

SO 3 Na+
Sunset Yellow
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [2]
[Total: 10]
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The substituted benzene compound

The substituted benzene compound

Y
Y

12
12

Examiners
For
Use
Examiners
Use

can be further substituted.

can be further substituted.

If Y is an electron-withdrawing group, the next substitution will be in position 3.

Y is
is an
an electron-withdrawing
electron-releasing group,
thethe
next
substitution
willwill
be be
mostly
in position
IfIf Y
group,
next
substitution
in position
3. 4.

If Y is an electron-releasing group, the next substitution will be mostly in position 4.

Y
Y

if Y is electron-withdrawing

if Y is electron-releasing

if Y is electron-withdrawing
+X

if Y is electron-releasing
+X

+X

+X

X
The following table lists some electron-withdrawing and electron-releasing substituents.

The following table lists some electron-withdrawing and electron-releasing substituents.

electron-withdrawing groups
electron-releasing groups
electron-withdrawing
groups
NO2

electron-releasing
CH3 groups

NO2
COCH
3

CHBr
CH
23

COCH
CO2H3

CH
NH22Br

CO2H

NH2

Use the above information to draw relevant structural formulae in the boxes in the schemes
below.
Use the above information to draw relevant structural formulae in the boxes in the schemes
below.
CH3

CH3

(i)
(ii)
(i)
(ii)

Br2 + Al Cl 3

Br2 + Al Cl 3
(i)
(ii)
(i)
(ii)

KMnO4 + OH
H+
KMnO4 + OH
H+

KMnO4 + OH
H+
KMnO4 + OH
H+

(i)
(ii)
(i)
(ii)

HNO3 + H2SO4

HNO3 + H2SO4

Sn + HCl
OH
Sn + HCl
OH

[5]
[Total: [5]
5]

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9
9
5
(4-aminophenyl)ethanoic acid (4-APEA) and its derivatives are being investigated as possible
5 (4-aminophenyl)ethanoic
acid (4-APEA)
and
its derivatives are being investigated as possible
drugs to treat chronic inflammation
of the
intestines.
drugs to treat chronic inflammation of the intestines.
The synthesis of 4-APEA from methylbenzene is shown in the following scheme.
The synthesis of 4-APEA from methylbenzene is shown in the following scheme.

For
Examiners
For
Use
Examiners
Use

CH2Cl
CH2Cl

CH3
CH3
I

II
II

HNO3I + H2SO4
HNO3 + H2SO4

NO2
NO2

III

III
CH2CO2H

CH2CN

CH2CO2H

IV

CH2CN

+
HIV
3O

H3O+
NO2

NH2

NH
2
4-APEA

NO2

H
4-APEA
(a) Draw the structures of the compounds G and H in the boxes above.

[2]

(a)(b)Draw
the structures
of the
compounds
G and
H in the
boxes above.
Suggest
reagents and
conditions
for the
following
steps.

[2]

(b) Suggest
reagents
and conditions for the following steps.

step
II
..........................................................................................................................................
step II
..........................................................................................................................................

step III
..........................................................................................................................................
step III

step V
..........................................................................................................................................

..........................................................................................................................................
step V
[3]
..........................................................................................................................................
[Total:[3]
5]
[Total: 5]

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10

96

Phenol and chlorobenzene are less reactive towards certain reagents than similar non-aromatic
compounds.
Thus hexan-1-ol can be converted into hexylamine by the following two reactions,
I
CH3(CH2)5OH
hexan-1-ol

II
CH3(CH2)5Cl
1-chlorohexane

CH3(CH2)5NH2
hexylamine

whereas neither of the following two reactions takes place.

OH

(a) (i)

Cl

NH2

Suggest reagents and conditions for

reaction I, ............................................................................................................... ,
reaction II. ............................................................................................................... .

(ii)

What type of reaction is reaction II? ..........................................................................

(iii)

Suggest a reason why chlorobenzene is much less reactive than 1-chlorohexane.

..................................................................................................................................
..................................................................................................................................
[4]

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For
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11
(b) Phenylamine can be made from benzene by the following two reactions.
NO2

III

(i)

IV

For
Examiners
Use

NH2

Suggest reagents and conditions for

reaction III, .............................................................................................................. ,
reaction IV. .............................................................................................................. .

(ii)

State the type of reaction for

reaction III, .............................................................................................................. ,
reaction IV. .............................................................................................................. .
[5]

(c) Suggest a reagent that could be used to distinguish phenylamine from hexylamine.
reagent and conditions ....................................................................................................
observation with phenylamine ..........................................................................................
observation with hexylamine.............................................................................................
[2]

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12
(d) Phenylamine is used to make azo dyes. In the following boxes draw the structural formula
of the intermediate D and of the azo dye E.

NH2
NaNO2 + HCl

CH3

T < 5C

OH
CH3

in NaOH(aq)

E
[2]
[Total: 13]

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For
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10

10
5

(a) (i)

Briefly explain why the benzene molecule is planar.

..................................................................................................................................
..................................................................................................................................
..................................................................................................................................

(ii)

Briefly explain why all the carbon-carbon bonds in benzene are the same length.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[2]

(b) Benzene can be nitrated by warming it with a mixture of concentrated sulfuric and
nitric acids.
(i)

By means of an equation, illustrate the initial role of the sulfuric acid in this
reaction.
..................................................................................................................................

(ii)

Name the type of reaction and describe the mechanism for the nitration reaction,
including curly arrows showing the movement of electrons and all charges.
type of reaction .........................................................................................................
mechanism

[4]
(c) State the reagents and conditions needed to convert benzene into chlorobenzene.
...................................................................................................................................... [1]

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For
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11
(d) Nitrobenzene undergoes further substitution considerably more slowly than chlorobenzene.
In nitrobenzene the incoming group joins to the benzene ring in the 3-position, whereas
in chlorobenzene the incoming group joins to the benzene ring in the 4-position.
(i)

For
Examiners
Use

Use these ideas to suggest the structures of the intermediate compounds Y and Z
in the following synthesis of 4-chlorophenylamine.

NH2
I

II

III

(ii)

Cl

Suggest the reagents and conditions needed for reaction III in the above
synthesis.
..................................................................................................................................
..................................................................................................................................

(iii)

Suggest the structural formulae of the products A, B, C and D of the following

reactions. If no reaction occurs write no reaction in the relevant box.

NH2
CH3COCl

Br2(aq)

Cl

OH (aq)

NaNO2
+ HCl

D
[8]
[Total: 15]

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10

11
5

(a) Compound G can be synthesised from benzene by the route shown below.

NH2

HNO3 +
H2SO4

step 2

55 C

step 3

H
O
CH3

OH

O
step 5

step 4

J (C6H5N2C )

G
(i)

Name the functional group formed in step 5.

..................................................................................................................................

(ii)

Draw the structures of the intermediates H and J in the boxes above.

(iii)

Suggest reagents and conditions for the following.

step 2 ........................................................................................................................
step 3 ........................................................................................................................
step 4 ........................................................................................................................
step 5 ........................................................................................................................
[7]

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11
(b) In a reaction discovered just over 100 years ago by the German chemist Karl Fries,
compound G is converted into compound K when it is heated with AlCl3.
Compound K is a structural isomer of G.

For
Examiners
Use

O
CH3

O
AC3

K (C8H8O2)

Compound K is a 1,4-disubstituted benzene derivative. It is insoluble in water, but

dissolves in NaOH(aq). It gives a white precipitate with Br2(aq), and a yellow precipitate
with alkaline aqueous iodine.
(i)

What is meant by the term structural isomerism?

..................................................................................................................................
..................................................................................................................................

(ii)

Use the information given above to name two functional groups in compound K.
..................................................................................................................................
..................................................................................................................................

(iii)

Suggest the structural formula of K, and draw it in the box above.

(iv)

Suggest structures for the aromatic products of the following reactions.

K

I2 + NaOH (aq)

NaOH (aq)
Br2 (aq)

[7]
[Total: 14]
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12
4

The following chart shows some reactions of ethylbenzene and compounds produced from it.
C

III

II

ethylbenzene

Br

IV

V
CO2H

NO2

Br

VI

O Na +
VII

NH2

N2C

X
(i)

Draw the structure of compound X in the box provided in the chart above.

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7
(ii)

Suggest reagents and conditions for each of the reactions, writing them in the spaces
below.
reaction I

For
Examiners
Use

......................................................................................................................

reaction II ......................................................................................................................
reaction III ......................................................................................................................
reaction IV ......................................................................................................................
reaction V ......................................................................................................................
reaction VI ......................................................................................................................
reaction VII ......................................................................................................................
[Total: 8]

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10

13
6

The following scheme outlines the production of some compounds from ethene.
H2C

For
Examiners
Use

CH2
I
Br

excess of NH3, heat in

ethanol under pressure

Br

KCN, heat in ethanol

C (C4H4N2)
B

III

II
CO2H

NH2

HO2C

H2N

D
SOC 2

E
(a) (i)

Suggest the reagent and conditions for reaction I.

..................................................................................................................................

(ii)

Describe the mechanism of reaction I by means of a diagram. Include all whole,

partial and induced charges, and represent the movements of electron pairs by
curly arrows.

[3]

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11
(b) Suggest the identities of compounds B, C and E, and draw their structures in the boxes
opposite.
[3]

For
Examiners
Use

(c) Suggest reagents and conditions for

reaction II,
..........................................................................................................................................
reaction III.
...................................................................................................................................... [2]
(d) During reaction II the nitrogen atoms are lost from the organic molecule. Suggest the
identity of the nitrogen-containing ion produced during this reaction.
...................................................................................................................................... [1]
(e) Compounds E and F react together to give a polymer and an inorganic product.
(i)

Draw one repeat unit of this polymer.

(ii)

Identify the inorganic product.

.............................................................................................................................. [2]

(f)

A 0.100 mol dm3 solution of compound D has a pH of 2.60.

(i)

Calculate the [H+] in this solution.

..................................................................................................................................
..................................................................................................................................

(ii)

Hence calculate the value of Ka of compound D.

..................................................................................................................................
..................................................................................................................................
[2]
[Total: 13]

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144

(a) (i)

Write the equation for a reaction in which ethylamine, C2H5NH2, acts as a

Brnsted-Lowry base.
..................................................................................................................................

(ii)

Ammonia, ethylamine and phenylamine, C6H5NH2, are three nitrogen-containing

bases.
Place these three compounds in order of basicity, with the most basic first.
most basic

(iii)

least basic

Explain why you have placed the three compounds in this order.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[4]

(b) (i)

Write an equation for a reaction in which phenol, C6H5OH, acts as a Brnsted-Lowry

acid.
..................................................................................................................................
The pKa values for phenol, 4-nitrophenol and the phenylammonium ion are given in
the table.
compound

pKa

OH
10.0

OH
7.2
O2N
+
NH3

(ii)

4.6

Suggest an explanation for the difference in the pKa values of phenol and nitrophenol.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................

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For
Examiners
Use

9
(iii)

Using the information in the table opposite, predict which of the following pKa values
is the most likely for the 4-nitrophenylammonium ion.

For
Examiners
Use

+
NH3
O2N
Place a tick ( ) in the box beside the value you have chosen.
pKa
1.0
4.5
7.0
10.0
(iv)

Explain your answer to part (iii).

..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[5]

(c) Phenylamine can be converted to 4-nitrophenol by the following steps.

OH

NH2
step 2

step 1

OH
step 3

NO2

B
(i)

Suggest the identity of intermediate B by drawing its structure in the box above.

(ii)

Suggest reagents and conditions for the three steps in the above scheme.
reagent(s)

conditions

step 1
step 2
step 3
[5]
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[Total: 14]
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15 7

Both phenol and phenylamine react similarly with

12 aqueous bromine.
For
Examiners
Use

12
BothState
phenol
phenylamine
similarly
with aqueous
bromine.
(a)
twoand
observations
youreact
would
make when
these reactions
take place.
7

Both phenol and phenylamine react similarly with aqueous bromine.

Use
For
Examiners
Use

(a) ..........................................................................................................................................
State two observations you would make when these reactions take place.
(a) State two observations you would make when these reactions take place.

..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................

..........................................................................................................................................
.....................................................................................................................................
[2]
..........................................................................................................................................

.....................................................................................................................................
[2]
(b) Describe
a simple test-tube reaction you could use to distinguish between phenol and
..................................................................................................................................... [2]
phenylamine.
(b) (b)
Describe
a asimple
youcould
coulduse
use
distinguish
between
phenol
Describe
simpletest-tube
test-tube reaction
reaction you
to to
distinguish
between
phenol
and and
phenylamine.
..........................................................................................................................................
phenylamine.
..........................................................................................................................................
..........................................................................................................................................
......................................................................................................................................[1]
......................................................................................................................................[1]
......................................................................................................................................[1]
(c) The
compound 3-aminobenzoic acid can be prepared by the following series of
reactions.
(c) The compound 3-aminobenzoic acid can be prepared by the following series of
(c) The compound 3-aminobenzoic acid can be prepared by the following series of
reactions.
CH3
CO2H
CO2H
CO2H
reactions.
CH3

CH3

CO2H

reaction IV
reaction IV

reaction IV

CO2H

CO2H

reaction V

CO2H

CO2H

reaction VI

reaction V

reaction V

reaction VI

NO2

NO2

Suggest suitable reagents and conditions for

Suggest suitable reagents and conditions for

CO2H

reaction VI
NH2

NO2

NH2

NH2

reaction
IV,
.......................................................................................................................
Suggest
suitable
reagents and conditions for
reaction
IV,
.......................................................................................................................
reaction
V,
........................................................................................................................
reaction
IV,V,
.......................................................................................................................
reaction
........................................................................................................................
reaction
.................................................................................................................. [4] [4]
reaction
VI.
..................................................................................................................
reaction
V,VI.
........................................................................................................................
[Total:
7]
[Total:
7]
reaction VI. ..................................................................................................................
[4]

[Total: 7]

Every reasonable effort has been made to trace all copyright holders where the publishers (i.e. UCLES) are aware that third-party material has been reproduced.
The publishers would be pleased to hear from anyone whose rights they have unwittingly infringed.

Every reasonable
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trace all copyright
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UCLES) areSyndicate
aware that
third-party
been reproduced.
University ofeffort
Cambridge
International
is part ofholders
the University
Cambridge
Local
(UCLES),
whichmaterial
is itself ahas
department
of
the University
Cambridge.
The publishers
wouldofbe
pleased to hear from anyone whose rights they have unwittingly infringed.
University
of Cambridge
Examinations
part of the
University
Cambridge
Local
Syndicate
(UCLES), which
is itself
a department
of
Every reasonable
effortInternational
has been made
to trace alliscopyright
holders
whereofthe
publishers
(i.e.Examinations
UCLES) are aware
that third-party
material
has been
reproduced.
UCLES 2004
9701/04/O/N04
the
University
of Cambridge.
The
publishers
would be pleased to hear from anyone whose rights they have unwittingly infringed.

University of Cambridge International Examinations is part of the University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of

the
UCLES
2004
University
of Cambridge.

UCLES 2004

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9701/04/O/N04

For
Examiners
Use

16
5

(a) State the reagents and conditions needed to convert benzene into
(i)

chlorobenzene,
...................................................................................................................................

(ii)

bromobenzene,
...................................................................................................................................

(iii)

nitrobenzene.
...................................................................................................................................
[4]

(b) The nitration of benzene is a two-step reaction that can be represented as follows.

NO2 +

B
(i)

Identify the cation A+. ...............................................................................................

(ii)

Draw the structure of the intermediate B in the box.

UCLES 2004

BILAL HAMEED

9701/04/M/J/04

[2]

9
(c) The position of substitution during the electrophilic substitution of arenes is determined
by the nature of the group already attached to the ring.

For
Examiners
Use

Electron-withdrawing groups such as CO2H or NO2 direct the incoming group to the
3-position.
CO2H

CO2H
nitration
NO2

On the other hand, electron-donating groups such as CH3 or NH2 direct the incoming
group to the 2- or 4- positions.
CH3

CH3
bromination

CH3
+

Br

Br
Use this information to suggest a likely structure for the organic product of each of the
following reactions.
(i)
NO2
bromination

(ii)
NH2
chlorination

CO2H
[2]
[Total: 8]

UCLES 2004

BILAL HAMEED

9701/04/M/J/04

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