SMJK CHUNG LING PULAU PINANG

PEPERIKSAAN PERCUBAAN STPM 2019

SEMESTER 3 CHEMISTRY
UPPER 6

NAME: ________________________________ CLASS: __________________ DURATION: 1 ½ HOURS

Section A (15%): Answer all the questions and write your answers in the boxes provided

1 6 11
2 7 12
3 8 13
4 9 14
5 10 15

1. When 240 cm3 of the gaseous hydrocarbon is completely burnt in oxygen, 720 cm 3 of carbon dioxide and
0.03 mol of water are formed. Which of the following formulae could be molecular formula of the
hydrocarbon? [ Molar volume of gas at room temperature is 24 000 cm 3]
A. C2H4 B. C2H6 C. C3H6 D. C3H8

2. Deuterium is a heavy isotope of hydrogen. Deuteriobenzene is reacted with a mixture of nitric acid and
sulphuric acid under controlled conditions so that only mononitration occurs. Assuming that carbon-
deuterium bonds could be broken similar manner like carbon hydrogen bonds, which of the following
represents the percentage of 3-nitrodeuteriumbenzene?
A. 16% B. 20% C. 33% D. 45%

3. The compound Ibuprophen is an important type of anti-inflammatory drug used to cure arthritis illness.

How many optical isomers are possessed by Ibuprophen?

A. 0 B. 2 C. 4 D. 6

4. Which of the following reagents results in nucleophilic substitution of 4-chloromethylphenol?

A. Br2 (aq) B. HNO3 (aq) C. NO2+ D. NH3

5. The reaction between bromoethane and aqueous sodium hydroxide to form ethanol is classified as
A. Free radical substitution
B. Electrophilic substitution
C. Electrophilic addition
D. Nucleophilic substitution

6. A compound P, C4H9Cl, undergoes hydrolysis to form an alcohol Q which is not oxidised by acidified
potassium manganate (VII) solution. Compound P and Q could be

P Q
A. CH3CH2CH2CH2Cl CH3CH2CH2CH2OH
B. CH3CH2CH2CH2Cl C(CH3)3OH
C. CH3CH2CH(CH3)Cl CH3CH2CH2CH2OH
D. C(CH3)3Cl C(CH3)3OH
7. Which of the following compounds does not give positive iodoform test?
A. CH3CH2OH
B. CH3CH(OH)CH2CH2CH3
C. C6H5CH(OH)CH3
D. CH3CH2CH(OH)CH2CH3

8. Pentaerythritol is an intermediate in the manufacture of paint. What conclusion about pentaerythritol can be
made from this structure?

A. It gives a precipitate with Tollens’ reagent

B. It is chiral
C. It can dehydrated to an alkene by concentrated sulphuric acid
D. It is soluble in water

9. When butan-2-ol is treated with excess of concentrated sulphuric acid at 180◦C, the structure of the main
product could be
A. CH3CH2CH(CH3)-0-CH(CH3)CH2CH3
B. CH3CH2COOCH3
C. CH3CH2COCH3
D. CH3CH=CHCH3

10. Compound X has the following properties.

i) It produce an orange precipitate with 2,4-dinitrophenolhydrazine
ii) It produce a yellow precipitate when warmed with an alkaline iodine solution
Compound X could be
A. C6H5CHO B. C6H5CH(OH)CH3 C. C6H5COCl D. C6H5COCH3

11. When a compound P which does not react with acidified solution of potassium dichromate (VI) , is heated
with aluminium oxide, compound Q is formed. The compound Q can decolourise bromine water. If Q is
treated with hydrogen bromide, 2-bromo-2-mmethylpropane is produced.
Compound P could be
A. Butan-2-one B. Propan-2-ol C. Butan-2-ol D. 2-methylpropan-2-ol

12. How many structural isomers of molecular formula C 4H8O can reduce a solution containing Ag(NH 3)2+ ion
(Tollens’ reagent) to form a silver mirror?
A. 1 B. 2 C. 3 D. 4

13. A monobasic organic acid Z has the following composition by mass: carbon, 40%; hydrogen, 6.7%; oxygen,
53.3%. it was found that 0.9 g of acid Z was completely neutralised by 10 cm 3 of 1.0 mol dm-3 sodium
hydroxide solution. What is the structural formula of Z?

A. C6H5COOH B. CH3CH2COOH C. CH3COCH2OH D. HOCH2CH2COOH

14. A compound U undergoes nucleophilic substitution reaction with aqueous ammonia to form compound W.
Ethylamine is produce when W is reduced by lithium tetrahydridoaluminate(III)
Compound U could be
 A. CH3CHO B. CH3COCl C. CH3CH2OH D. CH3CH2COOH
15. What is the correct order of acid strength (strongest first) for ethanoic acid, chloroethanoic acid and phenol?
A. CH3COOH, CH2ClCOOH, C6H5OH
B. CH2ClCOOH, C6H5OH, CH3COOH
C. CH2ClCOOH, CH3COOH, C6H5OH
D. C6H5OH, CH2ClCOOH, CH3COOH

Section B (15%): Answer all the questions

16. a) i Compound J, C9H10O produces an orange precipitate with 2,4-dinitrophenylhydrazine, What is the
molecular formula of J? Suggest four possible structures for J. [Assuming that aryl group only exist as C 6H5]
[4m]

ii If J gives a yellow precipitate on warming with alkaline iodine solution. What is J? [1m]

b)

The odour of banana is caused by the presence of the following organic compound with the structure above
i Give its IUPAC name. [1m]
____________________________________________________________________________________
ii Name the reagents used to produce this organic substance. [2m]
____________________________________________________________________________________

17. a) Complete the table of reaction products below [4m]

Ethanol Phenol Phenylmethanol

NaOH No reaction C6H5ONa No reaction

Na

HBr

CH3COCl

H2SO4 (dehydration)

b) When phenol is treated with a dilute nitric acid, a mixture of products are obtained.
i) Write the structural formulae of all products obtained. [2m]
 ii) Name the mechanism of the above reaction [1m]
____________________________________________________________________________________

Section C (30%): Answer any 2 questions

18. The ester of an alcohol J is used in perfume industry. The alcohol shows optical isomerism. When treated
with hot concentrated sulphuric acid, the optical isomer of J gives three substances, K, L, and M, which are
isomers to each other. Only small quantity of M is produced. Both K and L reacts with bromine to form 1,2-
dibromo-1-phenylpropane, N, where M with the same reagent gives 2,3-dibromo-1-phenylpropane.
a) (i) Suggest the structures of compounds J, K, L and M [4m]
(ii) Show the types of isomerism in compound K and L. Explain your answer [3m]
b) Describe the reaction mechanism of K N [5m]
c) What would you observe and name the organic product is formed, when K reacts with cold, dilute
alkaline potassium manganate (VII) solution? Write chemical equation involved. [3m]

19. A series of organic reactions is represented below:

Benzene X (C7H8) Y (C7H6Cl2) Z (C7H6O)
(i) (ii) (iii)
a) Name each compound X, Y and Z [3m]
b) Name the reagents and state the experimental conditions for the conversions of (i), (ii) and (iii). Write all
chemical equations involved. [6m]
c) Draw the structures of four compounds isomeric with Y [4m]
d) Compare reactivity between

[2m]

20. a) State the reagents and conditions required to carry out the following conversions
i) butan-2-one to 2-chlorobutane [3m]
ii) propan-1-ol to 2-methylpropanoic acid [7m]
b) Describe a chemical test to distinguish between benzoic acid and phenol [3m]
c) Methyl methanoate and ethanoic acid have the same relative molecular mass, but the boiling point of
methyl methanoate is 32◦C whereas ethanoic acid is 118◦C. Explain this statement. [2m]

Prepared by JS ONG
Checked by JN SIM