CONFTDENTIAL* 2

Section A [15 marksl

Answ,er all questions.

Indicate the correct answer on the Multiple-choice Answer Sheet provided.

Which is not true about an aromatic hydrocarbon, toluene?

A Has planar shape

B Has three zr bonds

C Has one electron donating group

D Has spz and spr hybridised carbon atoms

Which reaction involves a nucleophile as the attacking species?

A CH.:CH, + HBr --------+ CH.,CH,Br

B CH,CHO + HCN ---------+ CH,CHCN

I

OH
z-- t
c (a))
\\/
_' concentrated
--4
H,So.A (O)-
\vZ so.H + H o

D + NaoH,
@N,cr @"" @N:N+oNa
Two organic compounds, P and Q,have structural formulae as shown below.

H CICI H CICI
rtl
cH,-c-c-c-cooH ttt
CH.-C-C-C-COOH
ttl
H CIH HHCI
ttl
P O

Which statement is true about the organic compounds?

A P is a weaker acid than Q.
B Only Q rotates the plane polarised light.
C Only P undergoes dehydrohalogenation reaction.
D The inductive effect of Cl in P is more effective than that in O.

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Which reagent reacts with cyclohexane and 2-hexene?

A Hydrogen chloride
B Bromine in ultraviolet light
C Concentrated sulphuric acid

D Hot acidified potassium manganate(VII)

Which alkene exhibits cis-trans isomerism?

A 2-Methyl-2-hexene B 3-Methyl-3-hexene
C 2-Chloro-2-oentene D 3-Ethyl-3 -methyl- I -pentene

6 Which is the end product for the Friedel-Crafts acylation of benzene u ith ethanoyl chloride
then followed by the Friedel-Crafts alkylation with chloroethane?

A CH,CHT cH.cHr
cocH,

COCI

C cH,cHr D cH,cH,

cocH, co(]

7 The synthesis of 2-phenyl-2-butanol using Grignard reagent is shown in the reaction scheme
below.

CHtMgBr- Y
c6HrcocH,cHr x - 2-phenyl-2-butanol

What are represented by X and 12

X Y

A C6H,C(OH)(MgBr)CHrCHl H,O-
B C6HsC(CH-.)(MgBr)CH,CH., Hro
C C6H,C(CH.,)(OMgBr)CH,CH., H,o-
D C6H5C(CH2CHsXOMgBT)CHrCH, Hro

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8 The structural formula of a herbicide, { is shown below.

OH

cHCHTCHT

CH,

Which is true about ,X?

A Optically inactive
B Decolourises bromine water

C Releases white fumes when reacts with thionyl chloride

D Forms a fruity srnelling compound w'hen reacts with ethanoyl chlonde

9 Which is the fastest compound to react with anhydrous zinc chloride in concentrated
hydrochloric acid'/
A l-Butanol B 2-Butanol
C 2-Methyl-2-propanol D Phenol

l0 Which reaction does not involve during the preparation of phenylethanone?

A The ozonolysis of 2-phenylpropene

B The reaction between l-phenyl-1-ethanol and copper at 400 "C

C The Friedel-Crafts acylation of benzene with ethanoyl chloride

D The reaction between benzaldehyde and methylmagnesium bromide fbllowed by the

reaction with dilute hydrochloric acid

ll CHTCOC1 is a derivative compound of CH.COOH. Which is true about rhe compounds?

A CH.COOH has lower boiling point than CH.,COCI.

B CHTCOOH and CHTCOC1 undergo hydrolysis.

C CHTCOOH and CHTCOCI react with phenol.

D CHTCOOH is less reactive than CH,COCI.

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l2 The structural formulae of cinnamaldehyde and vanillin are shown belorv.

HO o
ttl
t\.-t\u tl
t-*,
fiHo
ocH.,
Cinnamaldehyde Vanillin

Which reagent is used to distinguish between the above cinnamaldehyde and vanillin'l
A Lucas reagent B Tollens'reagent
C lron(lll) chloride D Alkaline iodine solrrtion

13 Which are the products of the hydrolysis of phenyl ethanoate, CH.COOC6H., using excess
aqueous NaOH'l

A Phenol and ethanoic acid

B Phenol and sodium ethanoate

C Sodium phenoxide and ethanoic acid

D Sodium phenoxide and sodium ethanoate

14 Which statement is true about the chemical property of amines?

A Aniline is a weaker base than methanamine.
B Benzylamine undergoes coupling reaction to form an azo dye.
C Primary amines react with primary alkyl halides via Sn I mechanism
D Aromatic amines could be distinguished from aliphatic amines usrng iron(lll) chloride
solution.

l5 Which is not the property of polypropene in the presence of Ziegler-Natla catalyst?

A Opaque B Low density
C Cross-linked D High durability

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Section B [5 marksl
Answ,er all questions.

Write the ansv,ers in the spaces provided.

16 CompoundXis colourless gas and has a molecular formula of C*H*. The compound is obtained
a
by catalytic cracking of long chain hydrocarbons during refining of crude oil. The compound has
two structural isomers, I and Z. f and Z decolourise bromine in tetrachloromethane. Z exhibits
geometrical isomerism but )'does not.
(a) Draw the structural formulae of Y and Z. l2l

ri
I
\
\\
I aJ

-$\
I

(b) Write the IUPAC nomenclatures of Y and Z. l2l I

n\
I

I
a\
I
at
I ,\-
-,
I
sqJ
I

(c') Write the chemical equations for the following reactions: I

aJ
a
ar

(i) I and hot concentrated acidified KMnO., solution I e,)

tll I
o_

(ii) Z and hot concentrated acidified KMnO, solution tll

@ W is another structural isomer of compound X which does not dec'olourise bromine in

tetrachloromethane. Draw a structure of W. tll

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17 The reactions of propanal are shown in the reaction scheme below.

CH,
I

H,C g-CH,
- HO
OH
I

P ttl
H,C-9-C-Cl
concentrated H,SO.
I

KMnO.iH*, A

HH HO
H,C-C-C-OH
tl ttl
H,C-C-C-H
tl
HH
I

H
L)

(a) Draw the structural formulae of O. S and T. t3l

lo;
ts
t\
tF
l*
t\
l+
lgo
rs
r\
t:
lE
tl
ts
(b) Give the reagents P and R. t3l ;\
Reagent P:....

Reagent R: (l) ....

(2) .

(c) What is the function of CN in the fbrmation of O? tll

(c{) Suggest one chemical test to distinguish an aldehyde from a ketone.

tll

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Section C [30 marlcl

Ansv'er two questions only.

You mav ensw'er all the questions, but onlv the.firsl two
enswters w'ill l,e marked. Write the
onsv,ers on the ens\rer sheets providecl. Begin each ansv'er on a ne\4'page of'the ensw'er sheet.

l8 An isomer, R. has a molecular formula C.H,,Br. R undergoes hydrolysis rn aqueous alkaline to

form an alcohol, S. The rate of reaction of hydrolysis is independent to the c'oncentration of OH .
The dehydration of S produces two alkenes, T and IJ.
(a) (i) Draw the structural formulae of R, ,S, T andIJ. l4l
(ii) Write the mechanism for the formation of S. t3l
(iii) Why is the rate of reaction independent to the concentration of OH ? Give your
reason. tll
(b) Identify the major product of the dehydration reaction. Explain your answer. l2l
(c) Write all the chemical equations involved in the reaction. l2l
(d) Suggest a chemical test to difl-erentiate between R and f. t3l

19 (a) Thestructural fbrmulaeofacompound, X.and itsderivativecomporrnds, )'and Zare

shown below.

/=\
\y COOH COOH
(UhcooH
No,
X Z

(i) Arrange the compounds in descending order of acidity. Explarn your answer. t5]
(ii) Z could be prepared from X. State the reaction conditions and write the mechanism
of the reaction. tsl
(b) The structural formulae of propanoyl chloride and chloropropane are shown below.

o
tl
cHrcH,c cl cHrcH.,cH.,cl
-
Propanoyl chloride Chloropropane

(i) Why is the rate of hydrolysis of propanoyl chloride higher than that of chloropropane?
Explain your reasons. [3]
(ii) Write the chemical equations of the reactions in (6)(i). l2l

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20 (a) A tertiary amine, { has a molecular fbrmula of CeHrN.

(i) Deduce the structural formula ofX.
t3l
(ii) Explain the reaction between x and hydrochloric acid. t3l
(b) The structural formula of a tripeptide is shown below.

H,N-C H,-CON H-CH-CON H-CH.{OOH

(i) Explain the reaction between the tripeptide and ethanol.

t3l
(ii)Draw the structural fbrmulae and write the IUPAC nomenclatures of all amino acids
obtained upon completion of hydrolysis of the rripeptide.
l4l
(iii) Draw the structural fbrmulae of another tripeptides from the above amino acids.
[2]

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is over. CONFIDE,NTIAL*