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SECTION A
A CH3CH2CH(CH3)CH=CH2
B CH3C=CHCH3
CH3
C CH3CHBr
OH
D CH3CH=CHCHO
4 The total number of isomers (including stereoisomers) for a molecule with molecular
formula of C3H4Cl2 is
A 7 B 6
C 5 D 3
A. AlCl3 B. BF3
C. CH2=CH2 D. CH3CH2+
I II
CH3 CHCl2 CHO
Which of the following sets of reagents and conditions is the most suitable to be used in the
conversion of toluene to benzaldehyde as shown above ?
I II
A. excess Cl2, Fe NaOH(aq), reflux
B. excess Cl2, uv, boil KOH(aq), reflux
C. excess Cl2, NaOH(aq), ethanol, reflux
D. excess Cl2, uv, boil Cu, 400
OH
HOOCCCH2COOH
COOH
CH3
A. CH3COOH and NHCH3
14. Lactic acid can be formed from ethanol as shown in the reaction scheme below.
Name the types of reaction that occur in step I and step lll.
A Oxidation Hydrolysis
B Reduction Esterification
C Condensation Oxidation
D Dehydration Condensation
15. Which of the following compound is formed when ethanoy clhloride is reacted with
SECTION B
16. (a) Compound Q has molecular formula of C4H8O. Compound Q does not decolourise aqueous
bromine but it forms an orange precipitate with 2,4-dinitrophenylhydrazine.
Isomer of Q, P, forms a yellow precipitate when treated with iodine in aqueous sodium hydroxide.
P is also resistant to oxidation by acidified potassium dichromate(VI) aqueous solution.
(iii) Write a chemical equation for the reaction of P with iodine in aqueous sodium hydroxide.
[1 mark ]
(iv) State the observation when Q is added to Tollens reagent and the mixture is then warmed in a
hot water bath. Also write chemical equation for the reaction involved.
[2 marks]
.
(b) Compound Q and isomer P react with hydrogen cyanide in the presence of a base at 10-20 C to
form cyanohydrin.
(i) State the type of reaction that takes place. [1 mark ]
.
(ii) By using chemical equations, write the reaction mechanism for the reaction of Q with
hydrogen cyanide. [2 marks]
17. (a) Adrenaline is a hormone that acts as a stimulant .It has the structural formula shown below
(i) State the type of isomerism that can exist in the adrenaline molecule. [1 mark]
(ii) Draw the structural formula of the product formed when adrenaline reacts with
[2 marks ]
NaOH HCl
Structural formula Structural formula
SECTION C
(Answer 2 questions from this section)
18 (a) Compound Z is a dibasic acid that is found in fruits and it has the following composition by mass.
C, 35.8 % ; H, 4.5% ; O, 59.7%
Compound E evolves hydrogen gas when treated with sodium metal and it also reacts with acidified
potassium dichromate(VI) solution to form compound F.
(b) Compound B has been identified as being responsible for the distinctive aroma of raspberries. The
structural formula of compound B is as shown below.
HO CH2CH2COCH3
Compound B
(ii) Draw the structural formula of the organic product formed when compound B reacts with
aqueous bromine. [1 mark ]
(b) Give a chemical test to distinguish between ethylamine, C2H5NH2 and aniline, C6H5NH2
[3 marks]
(c) The structural formula of compound G is shown below. G can be used as a dye. It can be prepared
from an amine and a phenol under suitable conditions.
CH3
H3C N=N OH
CH3
Compound G
(i) Draw the structural formula of the amine and phenol that can be used in the preparation of G.
[2 marks]
(ii) State the reagents and conditions that are used in the preparation of G. Also write chemical
equations for the reactions involved [4 marks]
(iii) State the type of reaction that has taken place in (c)(ii) [1 mark ]
20.
++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++
ANSWERS
SECTION A
Q A Q A Q A
1 6 11
2 7 12
3 8 13
4 9 14
5 10 15
Section B
Q 16
. a) (i) Q = CH3CH2CH2CHO , CH3CH(CH3)CHO [2]
(ii) P = CH3COCH2CH3 [1]
(iii) CH3COCH2CH3 + I2 + OH- CHI3(s) + CH3CH2COO- [1]
(iv) Silver mirror is formed [1]
(ii)
(b) ( i) nucleophilic addition
(ii) dry ether, room temperature
18. (a)(i) C H O
No of moles : 35.8 4.5 59.7 . [1]
12 1 16
= 2.89 4.5 3.73
Simplest ratio 4 6 5
E.f of Z = C4H6O5. [1 ]
M.f of Z = ( C4H6O5.)n
n (C4H6O5) = 134
n=1 [1]
M.f of Z = C4H6O5 [1]
Z = HOOCCH(OH)CH2COOH [1]
E = CH3CH2OCOCH(OH)CH2COOCH2CH3 [1]
F = CH3CH2OCOCOCH2COOCH2CH3 [1]
O2N
O NNH NO2
Br [1]
HO CH2CH2COCH3
Br Total 15
19.(a) (i) CH2=CHCl [1]
(ii) H H H H
C C C C
H Cl H Cl [1]
(iii) PVC has polar CCl bond that can be hydrolysed when reacts with NaOH [1]
Polyethene does not have polar bond since it is a non-polar hydrocarbon. [1]
(b) Reagent : Add aqueous bromine or bromine water at room temperature and shake the mixture.
[1]
Observation : Aniline decolourises bromine and a white precipitate is formed. No observable change shown
by ethylamine [1]
Br
Equation : NH2 + 3 Br2 [1]
Br NH2 + 3HBr
(c) (i) CH Br [1]+[1]
3 NH2 CH3
CHO
3
(ii) Reagent : HNO2 or NaNO2,HCl H
Condition : 0-50C [2]
[1]
CH3 CH3
CH3 N2+Cl- + CH3 N=N
CHO3 O
+ HCl CH
[1] H 3
H
(iii)Electrophilic substitution [1]