Chemistry of Carbon Compounds

1 Which of following compounds is the major product of the reaction between

excess methane and chlorine?
A. Chloromethane
B. Dichloromethane
C. Trichloromethane
D. Tetrachloromethane □

2 Which of the following compounds are the products formed from the reaction
between methane and chlorine in the presence of light?
(1) Chloromethane
(2) Chloroform
(3) Hydrogen chloride
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3) □

3 Which of the following conditions are required for alkanes to undergo

substitution reactions with bromine?
(1) Sunlight
(2) High temperature
(3) High pressure
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3) □

4 Which of the following statements concerning the substitution reaction between

propane and chlorine are correct?
(1) It does not take place in the dark.
(2) It involves breakage of CH bonds and ClCl bonds.
(3) Hydrogen chloride is one of the products of the reaction.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

5 Which of the following statements concerning the substitution reaction between

methane and chlorine are correct?
(1) The product of the reaction is a mixture of chloroalkanes.
(2) The major product is tetrachloromethane if excess chlorine is used.
(3) Free radicals are produced during the reaction.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

6 Which of the following compound is the major product formed in an addition

reaction between hydrogen chloride and propene?
 Chemistry of Carbon Compounds

A. 1-chloropropane
B. 2-chloropropane
C. 1,2-dichloropropane
D. 2,2-dichloropropane
□

7 Which of the following statements are correct?

(1) Iron is used as a metal catalyst for speeding up hydrogenation.
(2) Bromine can be decolorized in darkness by pent-1-ene.
(3) 2-bromopropane is the major product formed in an addition reaction
between hydrogen bromide and propene.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3) □

8 Consider the following reaction:

+ HBr

Which of the following compounds is/are the possible major product(s) formed in the
above reaction?
(1)

(2)

(3)

A. (1) only
B. (2) only
C. (1) and (3) only
D. (2) and (3) only
□

9 Which of the following combinations about addition reactions is correct?

Addition reaction The major product
A. CH3CH=CH2 + HBr CH3CH2CH2Br
B. (CH3)2C=CH2 + HBr (CH3)3CBr
C. BrCH=CH2 + HBr BrCH2CH2Br
D. (CH3)3CCH=CH2 + HBr (CH3)3CCH2CH2Br
□
10 Which of the following statements concerning but-1-ene are correct?
(1) It reacts with hydrogen chloride to give 1-chlorobutane as the major
product.
 Chemistry of Carbon Compounds

(2) It can decolorize acidified potassium permanganate solution.

(3) It undergoes hydrogenation in the presence of platinum as metal catalyst
with heating.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

11 Which of the following compounds is the major product formed from the
reaction between 2,5-dimethylhex-2,4-diene and hydrogen bromide?
A. 3,5-dibromo-2,5-dimethylhexane
B. 2,4-dibromo-2,5-dimethylhexane
C. 3,4-dibromo-2,5-dimethylhexane
D. 2,5-dibromo-2,5-dimethylhexane
□

12 Which of the following statements concerning halogenation and

hydrohalogenation is/are correct?
(1) Both of them follow Markovnikov’s rule.
(2) Both of them involve unsaturated hydrocarbons.
(3) Both of them are substitution reactions.
A. (1) only
B. (2) only
C. (1) and (3) only
D. (2) and (3) only
□

13 Which of the following can be classified as addition reactions?

(1) Reaction between ethene and hydrogen
(2) Reaction between ethene and hydrogen chloride
(3) Reaction between methane and chlorine
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3) □

14 Which of the following statements concerning propene are correct?

(1) It reacts with hydrogen in the presence of platinum and heating to give propane.
(2) It reacts with hydrogen chloride to give 1-chloropropane as the major product.
(3) It decolorizes bromine solution in the dark.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□
15 Which of the following statements about propene is correct?
A. It can decolorize acidified potassium dichromate solution.
B. It can be prepared by heating propan-1-ol with dilute sulphuric acid.
C. It reacts with hydrogen in the presence of nickel to give propane.
D. It reacts with hydrogen chloride to give 1-chloropropane as the major
 Chemistry of Carbon Compounds

product. □

16 Which of the following compounds is the major product for the reaction between
2-methylpropene and hydrogen chloride?
A. 1-chloro-2-methylpropane
B. 1,2-dichloro-2-methylpropane
C. 2-chloro-2-methylpropane
D. 2-methylpropane □

17 Which of the following statements about hydrogenation of alkenes is

INCORRECT?
A. It requires metal catalysts such as platinum and nickel.
B. It requires heating.
C. It is an endothermic reaction because energy is required to break the C=C
bonds.
D. It involves formation of CH bonds. □

18 Which of the following compounds is/are the product(s) formed from the
reaction between pent-1,4-diene and excess bromine in water?
(1) 1,2-dibromopentane
(2) 1,2,4,5-tetrabromopentane
(3) 4,5-dibromopentane
A. (1) only
B. (2) only
C. (1) and (3) only
D. (2) and (3) only □

19 Which of the following compounds is the major product formed from the
reaction between but-1,3-diene and hydrogen iodide?
A. 1,4-diiodobutane
B 2,4-diiodobutane
C. 1,3-diiodobutane
D. 2,3-diiodobutane □

20 Which of the following reactions are addition reactions?

(1) CH2=CHCH=CH2 + HI
(2) CH3CH2CH2CH3 + Cl2
(3) CH2=CHCH2CH3 + H2
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

21 Which of the following statements concerning the substitution reaction between

bromoethane and hydroxide ions are correct?
(1) Ethanol is one of the products.
(2) An organic solvent is required for the reaction.
(3) The reaction involves the breakage of the CBr bond.
A. (1) and (2) only
B. (1) and (3) only
 Chemistry of Carbon Compounds

C. (2) and (3) only

D. (1), (2) and (3) □

22 Which of the following compounds could undergo substitution reactions?

(1) CH3CH=CHCH3
(2) CH3CH2CH2CH3
(3) CH3CH2CH2CH2Br
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3) □

23 Which of the following reactions are substitution reactions?

(1) CH3CH2CH2CH2I + OH
(2) CH3CH2CH2CH3 + Cl2
(3) CH3CH=CHCH3 + H2
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3) □

24 Which of the following statements about the reaction between 2-iodobutane and
NaOH(aq) are correct?
(1) The products of the reaction are butan-2-ol and sodium iodide.
(2) The reaction will be faster if 2-chlorobutane replaces 2-iodobutane.
(3) The reaction involves the breakage of the CI bond.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

25 Sodium hydroxide solution was added to a sample of chloromethane in a test

tube. Then, a small amount of acidified silver nitrate solution was added to the
reaction mixture. What could be observed?
A. Gas bubbles were formed.
B. The solution turned silvery.
C. White precipitate was formed.
D. No observable change.
□
 Chemistry of Carbon Compounds

26 Which of the following reagents are used to convert propan-2-ol to 2-

bromopropane?
(1) H2SO4(l) + KBr(s)
(2) Br2(l) + CCl4(l)
(3) PBr3(l)
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

27 Which of the following statements concerning propan-1-ol are correct?

(1) It can be oxidized to give propanal.
(2) It can be oxidized to give propanoic acid.
(3) It can be dehydrated to give propene.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

28 Consider the following reaction:

Which of the following compounds is the major product of the above reaction?
A.

B.

C.

D.

□
 Chemistry of Carbon Compounds

29 Consider the following reactions:

Reaction 1:

Reaction 2:

Which of the following compounds is the major product of reaction 2?

A. 1-chlorobutane
B. 2-chlorobutane
C. 1,2-dichlorobutane
D. 2,2-dichlorobutane □

30 Which of the following reactions are substitution reactions?

(1) The reaction between hydrogen chloride and propan-1-ol.
(2) The reaction between hydrogen bromide and ethene.
(3) The reaction between bromine and methane.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3) □

31 Which of the following statements concerning alcohols is INCORRECT?

A. 2-methylpropan-2-ol is a tertiary alcohol.
B. All the alcohols can be oxidized to carboxylic acids.
C. An alcohol can be dehydrated to an alkene by treating with concentrated
sulphuric acid at 180C.
D. Phosphorus trihalides can convert an alcohol to a haloalkane. □

32 Which of the following reactions are correct?

(1) 3CH3CH(OH)CH2CH2CH3 + PBr3  3CH3CHBrCH2CH2CH3
(2) CH2(OH)CH2(OH) + 4[O]  (COOH)2 + 2H2O
(3) CH3CH2Br + NaOH  CH3CH2OH + NaBr
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3) □

33 Which of the following compounds is/are the possible product(s) formed from
the oxidation of butan-2-ol?
(1) Butanone
(2) Butanoic acid
(3) Butanal
A. (1) only
B. (2) only
C. (1) and (3) only
D. (2) and (3) only
□

34 Which of the following compounds could be collected from the oxidation of

 Chemistry of Carbon Compounds

pentan-1-ol?
(1) Pentanoic acid
(2) Pentanal
(3) Pentanone
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3) □

35 Which of following statements concerning phosphorus tribromide are correct?

(1) It can convert butan-2-ol to 2-bromobutane.
(2) It can convert but-2-ene to 2,3-dibromobutane.
(3) It is formed from the reaction between phosphorus and bromine.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3) □

36 Which of the following compounds is/are the possible product(s) formed from
the oxidation of methanol?
(1) Methanal
(2) Methyl methanoate
(3) Methanoic acid
A. (1) only
B. (2) only
C. (1) and (3) only
D. (2) and (3) only
□

37 Which of the following reactions can produce a haloalkane?

(1) The reaction between butan-1-ol and phosphorus trichloride.
(2) The reaction between but-1-ene and hydrogen bromide.
(3) The reaction between propene and chlorine solution.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

38 Which of the following compounds is the product formed from the reaction
between ethanol and solid potassium bromide in the presence of concentrated
sulphuric acid?
A. CH3CH2Br
B. BrCH2CH2Br
C. CH3CH3
D. BrCH=CHBr
□

39 Which of following statements concerning the compound below is/are correct?

 Chemistry of Carbon Compounds

(1) It is a primary alcohol.

(2) It reacts with acidified potassium dichromate solution to give a ketone.
(3) It reacts with hydrogen chloride to give 2,2-dichlorobutan-1-ol as the major
product.
A. (1) only
B. (2) only
C. (1) and (3) only
D. (2) and (3) only
□

40 Which of the following compounds are NOT secondary alcohols?

(1)

(2)

(3)

A. (1) and (2) only

B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

41 Which of the following statements concerning the reaction between butan-1-ol

and hydrogen bromide are correct?
(1) The product of the reaction is bromobutane.
(2) The reaction involved is a substitution reaction.
(3) Hydrogen bromide should be made by heating bromine with red
phosphorus.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

42 Compound X is an alcohol with the condensed formula of CH3CH(OH)C2H5.

Which of the following statements concerning compound X is/are correct?
 Chemistry of Carbon Compounds

(1) It is a secondary alcohol.

(2) It undergoes dehydration in the presence of dilute sulphuric acid at 180C to
give an alkene and water.
(3) It can be oxidized to butanoic acid.
A. (1) only
B. (2) only
C. (1) and (3) only
D. (2) and (3) only
□

43 Consider the following reaction:

3CH3CH2CH2OH + PI3  3CH3CH2CH2I + Compound X
What is compound X?
A. P2O5
B. P4O10
C. H3PO3
D. H3PO4
□

44 Which of following reagents can convert primary alcohols to carboxylic acids?

(1) Acidified potassium dichromate solution
(2) Acidified potassium permanganate solution
(3) Acidified potassium nitrate solution
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

45 Which of the following statements concerning propanone are correct?

(1) It has a lower boiling point than propanoic acid.
(2) It can be reduced to give propan-2-ol.
(3) It can be oxidized to give propanoic acid.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□
 Chemistry of Carbon Compounds

46 Consider the following reaction:

Which of the following compounds is the major product of the above reaction?
A.

B.

C.

D.

47 Which of the following compounds can change acidified potassium dichromate

solution from orange to green in an appropriate condition?
(1) Butanal
(2) Pentan-2-one
(3) Hexan-1-ol
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

48 Which of the following statements concerning LiAlH4 are correct?

(1) It should be stored in paraffin oil.
(2) It should be used in dry ether.
(3) It is soluble in common organic solvents.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□
 Chemistry of Carbon Compounds

49 Which of the following statements concerning the compound below are correct?

(1) It has no reaction towards acidified potassium dichromate solution.

(2) It can react with lithium aluminium hydride in dry ether, followed by dilute
hydrochloric acid to give

(3) It is optically inactive.

A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

50 Which of the following statements concerning primary alcohols is/are correct?

(1) They can be dehydrated to alkenes by treating with concentrated sulphuric acid
at 180C.
(2) They can be formed by reducing ketones with LiAlH4 in dry ether and dilute
acids.
(3) They can be formed by reacting haloalkanes with sodium hydroxide solution.
A. (1) only
B. (2) only
C. (1) and (3) only
D. (2) and (3) only
□

51 Which of the following compounds is the product formed from the reaction
between butanal and acidified potassium dichromate solution?
A. But-1-ene
B. Butan-1-ol
C. Butane
D. Butanoic acid
□

52 Which of the following compounds is the product formed from the reaction
between butane-2,3-dione and LiAlH4 in dry ether followed by a dilute acid?
A. 3-oxobutan-2-ol
B. 3-hydroxybutan-2-one
C. 2-hydroxybutan-3-one
D. Butane-2,3-diol
□
 Chemistry of Carbon Compounds

53 Which of the following compounds is the product formed from the reaction
between 2-bromopent-3-one and LiAlH4 in dry ether followed by a dilute acid?
A. Pent-2,3-diol
B. 2-bromopentan-3-ol
C. 2-hydroxypentan-3-one
D. 2-bromopentan-3,3-diol
□

54 Consider the following reaction:

Which of the following compounds is the major product of the above reaction?
A.

B.

C.

D.

55 Consider the following reactions:

What is compound B?
A.

B.

C.
D.
□

56 Which of the following reagents can be used to convert propanal to propanoic

 Chemistry of Carbon Compounds

acid?
A. Concentrated sulphuric acid
B. Acidified potassium dichromate solution
C. Lithium aluminium hydride in dry ether
D. Thionyl chloride
□

57 Which of the following reagents can be used to oxidize propan-1-ol to propanoic

acid?
(1) Acidified potassium dichromate solution
(2) Acidified potassium permanganate solution
(3) Lithium aluminium hydride in dry ether
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

58 Which of the following compounds can be oxidized by acidified potassium

dichromate solution?
A. HCOOH
B. CH3CH2OH
C. CH3COCH2CH3
D. (CH3)3COH
□

59 Consider the following reactions:

Which of the following combinations is correct?

Compound X Reagent Y
A. CH3CH2CHO Concentrated H2SO4
B. CH3CH2CHO Acidified K2Cr2O7
C. CH3CH2CH2OH Concentrated H2SO4
D. CH3CH2CH2OH Acidified K2Cr2O7
□

60 Which of the following reactions can produce a primary alcohol?

(1) CH3CH2CH2Cl + OH
(2) CH3CH2CH2COOH + LiAlH4 in dry ether + H+
(3) CH3COCH3 + LiAlH4 in dry ether + H+
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

61 Which of the following are the functions of concentrated sulphuric acid in the
esterification of a carboxylic acid?
(1) It acts as a catalyst.
 Chemistry of Carbon Compounds

(2) It removes water produced from the reaction.

(3) It precipitates the ester formed.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

62 Which of the following chemicals are required for converting carboxylic acids to
amides?
(1) SOCl2
(2) HNO3
(3) NH3
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

63 Which of the following compounds is the product formed from the reaction
between butanoic acid and LiAlH4 in dry ether followed by a dilute acid?
A. Butanal
B. Butan-1-ol
C. Butane
D. Butene
□

64 Which of the following statements concerning esters are correct?

(1) An ester is a colourless volatile liquid with a characteristic sweet fruity
smell.
(2) Methyl ethanoate can be hydrolysed to ethanoic acid and methanol by
heating under reflux with dilute hydrochloric acid.
(3) Methyl propanoate can be formed by heating a mixture of propanoic acid
and methanol with concentrated sulphuric acid.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□
 Chemistry of Carbon Compounds

65 Which of the following statements concerning butan-1-ol are correct?

(1) It can be converted to but-1-ene in the presence of concentrated sulphuric
acid at 180C.
(2) It can be oxidized to butanoic acid by heating under reflux with acidified
potassium dichromate solution.
(3) It is one of the products formed from the acid hydrolysis of butyl
methanoate.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

66 Which of the following statements concerning acid hydrolysis of ethyl butanoate

are correct?
(1) The products of acid hydrolysis are butanoic acid and ethanol.
(2) The acid hydrolysis does not go to completion.
(3) The acid hydrolysis can be catalysed by dilute hydrochloric acid.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

67 Which of the following statements concerning hydrolysis of an ester are correct?

(1) It can be carried out either in acidic or alkaline medium.
(2) It can be catalysed by either strong acids or alkalis.
(3) It can produce an alcohol as one of the products.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

68 Which of the following statements concerning an amide is/are correct?

(1) Alkaline hydrolysis of an amide gives ammonia.
(2) An amide can be reduced to carboxylic acid by LiAlH4 in dry ether.
(3) An amide can be formed by treating a carboxylic acid with SOCl2 and then
NH3.
A. (1) only
B. (2) only
C. (1) and (3) only
D. (2) and (3) only
□
 Chemistry of Carbon Compounds

69 Consider the following reaction:

Which of the following compounds are the products of the above reaction?
A.

B.

C.

D.

70 Which of the following compounds are the products formed from the alkaline
hydrolysis of propanamide with sodium hydroxide solution?
A. Propanone and ammonia
B. Propanoic acid and ammonium ion
C. Propan-1-ol and ammonium ion
D. Sodium propanoate and ammonia □

71 Which of the following compounds is the product formed from the reaction
between CH3CH2CONH2 and NaOH(aq)?
A. CH3CH2COOH
B. CH3CH2COONa+
C. CH3CH2CH2NH2
D. CH3CH2CHO □

72 Which of the following reactions would give propanoic acid?

(1) The reaction between propan-2-ol and acidified potassium permanganate
solution.
(2) The reaction between methyl propanoate and water in the presence of dilute
sulphuric acid.
(3) The reaction between propanamide and water in the presence of dilute
hydrochloric acid.
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3)
□

73 Which of the following reactions would give butanoate ion?

 Chemistry of Carbon Compounds

(1) Adding sodium metal to butanoic acid.

(2) Heating ethyl butanoate with dilute acid under reflux.
(3) Heating butanamide with dilute sodium hydroxide solution under reflux.
A. (1) only
B. (2) only
C. (1) and (3) only
D. (2) and (3) only □

74 Which of the following compounds are the products formed by heating a mixture
of propanamide and dilute hydrochloric acid under reflux?
(1) Propanoic acid
(2) Ammonia
(3) Ammonium ion
A. (1) and (2) only
B. (1) and (3) only
C. (2) and (3) only
D. (1), (2) and (3) □

A. Both statements are true and the 2nd statement is a correct explanation of the
1st statement.
B. Both statements are true and the 2nd statement is NOT a correct explanation of
the 1st statement.
C. The 1st statement is false but the 2nd statement is true.
D. Both statements are false.
75
The hydrogenation of alkenes can be Either platinum or nickel is a metal catalyst
catalysed by either platinum or nickel. used to speed up the hydrogenation.
□
76
The major product of the reaction between Markovnikov’s rule states that the
2-methylbut-2-ene and hydrogen chloride hydrogen atom in hydrogen chloride is
is 2-chloro-2-methylbutane. added to the carbon atom of the carbon-
carbon double bond that already carries the
larger number of hydrogen atoms.

□
77
An alcohol can be oxidized to give an In dehydration, hydrogen and oxygen in the
alkene. ratio of 2:1 are eliminated from a
compound.
□
78
Ethanol can be oxidized by potassium Ethanol can be oxidized to ethanoic acid.
dichromate solution.
□
79
Carboxylic acids can be reduced to LiAlH4 is a mild reducing agent.
alcohols by mixing with LiAlH4 in dilute
acid.
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1 A When methane is in excess, chloromethane is the major product.
2 D The product formed from the above reaction is a mixture of chloroalkanes, including
chloromethane, dichloromethane, trichloromethane and tetrachloromethane. Chloroform
is the trivial name of trichloromethane.
 Chemistry of Carbon Compounds

3 A
4 D The reaction only takes place in the presence of sunlight which supplies energy to
break the ClCl bonds in chlorine molecules.
5 D
6 B According to Markovnikov’s rule, the hydrogen atom in hydrogen chloride is added
to the carbon atom of the carbon-carbon double bond that already carries the larger
number of hydrogen atoms. Then the chlorine atom is added to the carbon atom carrying
fewer hydrogen atoms.
7 C (1) is incorrect. A finely divided metal catalyst such as Pt, Pd or Ni is often used to
speed up the hydrogenation.
8 C According to Markovnikov’s rule, the hydrogen atom in hydrogen bromide is added
to the carbon atom of the carbon-carbon double bond that already carries the larger
number of hydrogen atoms. Then the bromine atom is added to the carbon atom carrying
fewer hydrogen atoms.
9 B According to Markovnikov’s rule, the hydrogen atom in HBr is added to the carbon
atom of the carbon-carbon double bond that already carries the larger number of
hydrogen atoms. The major products of the reactions for A, C and D should be
CH3CHBrCH3, Br2CHCH3 and (CH3)3CCHBrCH3 respectively.
10 C According to Markovnikov’s rule, the hydrogen atom in hydrogen chloride is added
to the carbon atom of the carbon-carbon double bond that already carries the larger
number of hydrogen atoms. Then the chlorine atom is added to the carbon atom carrying
fewer hydrogen atoms. Therefore, the major product is 2-chlorobutane.
11 D According to Markovnikov’s rule, the hydrogen atom in hydrogen bromide is added
to the carbon atom of the carbon-carbon double bond that already carries the larger
number of hydrogen atoms. Then the bromine atom is added to the carbon atom carrying
fewer hydrogen atoms. Therefore, the major product is 2,5-dibromo-2,5-
dimethylhexane.
12 B Both of them are addition reactions.
13 A (3) is a substitution reaction.
14 B According to Markovnikov’s rule, the major product of the reaction between propene
and hydrogen chloride is 2-chloropropane.
15 C A is incorrect. Propene can decolorize acidified potassium permanganate solution but
not acidified potassium dichromate solution. B is incorrect. Propene can be prepared by
treating propan-1-ol with concentrated sulphuric acid at 180C. D is incorrect.
According to Markovnikov’s rule, propene reacts with hydrogen chloride to give 2-
chloropropane as the major product.
16 C According to Markovnikov’s rule, the major product of the reaction is 2-chloro-2-
methylpropane.
17 C Hydrogenation of alkenes is exothermic. This is because the energy released during
the formation of new CH bonds is more than the energy needed for partially breaking
the original C=C bonds.
18 B
19 D According to Markovnikov’s rule, the major product of the reaction is 2,3-
diiodobutane.
20 B (2) is a substitution reaction between butane and chlorine.
21 B For (2), OH ions are in aqueous solution e.g. sodium hydroxide solution.
22 C CH3CH2CH2CH3 undergoes substitution reaction with bromine in sunlight to give
CH3CH2CH2CH2Br. CH3CH2CH2CH2Br undergoes substitution reaction with hydroxide
ions to give CH3CH2CH2CH2OH.
23 A (3) is an addition reaction between but-2-ene and hydrogen.
24 B Since the strength of CCl bond is stronger than that of CI bond, the reaction
between 2-chlorobutane and NaOH(aq) should be slower.
25 C The chlorine atoms in chloromethane are substituted by hydroxide ions, so the
reaction mixture contains chloride ions which react with silver ions to form silver
chloride, a white precipitate.
 Chemistry of Carbon Compounds

26 B (2) is the reagent used to convert alkene to dihaloalkane.

27 D Propan-1-ol is a primary alcohol which is first oxidized to propanal (aldehyde) and is
then further oxidized to propanoic acid (carboxylic acid).
28 D Primary alcohols are first oxidized to aldehydes and are then further oxidized to
carboxylic acids. Secondary alcohols are oxidized to ketones which are resistant to be
further oxidized. Tertiary alcohols are resistant to oxidation.
29 B Butan-1-ol is dehydrated to but-1-ene by treating with concentrated sulphuric acid at
180C. Therefore, compound X is but-1-ene. Then, but-1-ene undergoes
hydrohalogenation to give two products, 1-chlorobutane and
2-chlorobutane. According to Markovnikov’s rule, 2-chlorobutane is the major product.
30 B (2) is an addition reaction.
31 B Only primary alcohols can be oxidized to carboxylic acids. Secondary alcohols are
oxidized to ketones and tertiary alcohols do not undergo oxidation under the same
conditions.
32 D
33 A Butan-2-ol is a secondary alcohol, so it can be oxidized to butanone (ketone) only.
Butanone is resistant to further oxidation, so it is left as the end product.
34 A Pentan-1-ol is a primary alcohol, so it is first oxidized to pentanal and is then further
oxidized to pentanoic acid. The intermediate product – pentanal could be collected by
special experimental set-up.
35 B
36 C Since methanol is a primary alcohol, it is first oxidized to methanal and is then
further oxidized to methanoic acid.
37 D
38 A Firstly, KBr reacts with concentrated H2SO4 to give HBr and KHSO4. Then, HBr
formed reacts with CH3CH2OH to give CH3CH2Br.
39 A According to Markovnikov’s rule, the hydrogen atom of hydrogen chloride should be
added to the carbon atom of the carbon-carbon double bond that already carries the
larger number of hydrogen atoms. Besides, the OH group is substituted by Cl.
Therefore, the major product should be 1,2,2-trichlorobutane. The compound reacts with
acidified potassium dichromate solution to give a carboxylic acid.
40 B (1) is a primary alcohol, (2) is a secondary alcohol and (3) is a tertiary alcohol.
41 A Hydrogen bromide should be made by heating solid potassium bromide with
concentrated sulphuric acid.
42 A (2) is incorrect because concentrated sulphuric acid should be used instead of the
dilute one for the dehydration of an alcohol. (3) is incorrect. Since compound X is a
secondary alcohol, it is only oxidized to a ketone which is resistant to further oxidation.
43 C
44 A (1) and (2) are common oxidizing agents.
45 A (3) is incorrect because ketones are resistant to oxidation.
46 B Lithium aluminium hydride in dry ether has no reaction with alkenes. It is used to
reduce aldehydes to alcohols.
47 B Pentan-2-one is a ketone which is resistant to oxidation, therefore it does not react
with acidified potassium dichromate solution.
48 A LiAlH4 is insoluble in common organic solvents, it is used as a solid reducing
reagent.
49 B (2) is incorrect. The ketone group should also be reduced to a secondary alcohol,

50 C For (2), ketones are reduced to secondary alcohols. For (3), the reactions between
haloalkanes and sodium hydroxide solution could give primary alcohols, secondary
alcohols and tertiary alcohols.
 Chemistry of Carbon Compounds

51 D
52 D The ketone is reduced to a diol.
53 B The ketone is reduced to an alcohol.
54 C There are two types of reactions. One is a substitution of the bromine atom by a
hydroxide ion and the other is a neutralization between COOH group and sodium
hydroxide.
55 C Lithium aluminium hydride in dry ether is used to reduce propanoic acid to propan-1-
ol. Therefore, compound A is propan-1-ol. Then propan-1-ol is heated with a mixture of
phosphorus and bromine to give 1-bromopropane.
56 B Propanal does not react with concentrated sulphuric acid and thionyl chloride.
Lithium aluminium hydride in dry ether is used to reduce propanal to propan-1-ol.
57 A Lithium aluminum hydride in dry ether is used to reduce carboxylic acids, aldehydes
and ketones to alcohols.
58 B CH3COCH2CH3 is a ketone and (CH3)3COH is a tertiary alcohol. Both of them are
resistant to oxidation. Only primary and secondary alcohols can be oxidized by acidified
potassium dichromate solution.
59 D CH3CH2CH2Cl undergoes substitution with hydroxide ions to give CH3CH2CH2OH.
Then, CH3CH2CH2OH is oxidized by acidified K2Cr2O7 to give CH3CH2COOH.
60 A (3) only produces a secondary alcohol.
61 A
62 B
63 B Butanoic acid is reduced to butan-1-ol.
64 D
65 D Since butan-1-ol is a primary alcohol, it can be oxidized to butanoic acid. The
products formed from the acid hydrolysis of butyl methanoate are methanoic acid and
butan-1-ol.
66 D The acid hydrolysis does not go to completion because it is a reversible reaction.
67 D There are acid hydrolysis and alkaline hydrolysis of an ester respectively.
68 C An amide is hydrolysed to give a carboxylate ion and ammonia by heating under
reflux with sodium hydroxide solution.
69 A There are two types of reactions. One is a substitution of the chlorine atom by a
hydroxide ion and the other is an alkaline hydrolysis of an amide to give a carboxylate
ion and ammonia.
70 D
71 B CH3CH2CONH2 undergoes alkaline hydrolysis to give carboxylate ion,
CH3CH2COO.
72 C Propan-2-ol reacts with an oxidizing agent to give a ketone. However, ketones are
resistant to further oxidation.
73 C Heating ethyl butanoate with dilute acid under reflux will give butanoic acid and
ethanol.
74 B
75 A
76 A The reaction may give 2 products, 2-chloro-2-methylbutane and 2-chloro-3-
methylbutane. However, according to Markovnikov’s rule, 2-chloro-2-methylbutane is
the major product.
77 C An alcohol is converted to an alkene by dehydration, not oxidation.
 Chemistry of Carbon Compounds

78 C Ethanol can be oxidized by acidified potassium dichromate solution. Ethanol is a

primary alcohol, so it can be oxidized to ethanoic acid.
79 D Carboxylic acids can be reduced to alcohols by mixing with LiAlH4 in dry ether first,
the reaction mixture is then treated with a dilute acid. LiAlH4 must be used in dry ether
solvent because it reacts violently with water. Besides, LiAlH4 is a strong reducing
agent.