SMJK Chung Ling Pulau Pinang Peperiksaan Percubaan STPM 2019 Semester 3 Chemistry Upper 6
SMJK Chung Ling Pulau Pinang Peperiksaan Percubaan STPM 2019 Semester 3 Chemistry Upper 6
SMJK Chung Ling Pulau Pinang Peperiksaan Percubaan STPM 2019 Semester 3 Chemistry Upper 6
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.
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?
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
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?
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
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]
____________________________________________________________________________________
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]
____________________________________________________________________________________
[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