REVISION SET 2

CHEMISTRY DK024

SECTION A
4. Identify all functional groups present in
1. Which of the following molecules is
the molecule below.
NOT an organic compound?
OH
A. NH2

N CONH2
N

NH COOH
N

B. H A. Amino, ester, hydroxyl

H C H B. Hydroxy, carboxyl, amide
H C. Hydroxyl, carboxyl, amide
C. O C O D. Hydroxyl, carbonyl, amino
D. O
C
H2N NH2 5. Which of the following solvent can be
used to dissolve an alkane?

2. What is the type of reaction involved in A. H2O

the synthesis of compoud G below? B. CCl4

C. Ethanol
H2, Pt
H2C CH2 H3C CH3 D. Propanoic acid
G

A. Elimination 6. Which of the following is a

B. Addition propagation step in the reaction
C. Substitution between methane and bromine liquid?
D. Oxidation A. Cl2 2 Cl

B.
3. How many structural isomers present
CH3 + Cl CH3Cl

in a hydrocarbon with a molecular C. Cl + CH4 CH3 + HCl

formula of C4H8?
D. CH
A. 4 3 +HCl CH4 + Cl

B. 5
C. 6
D. 7

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7. Name the alkene below according to 11. Bromination of benzene is carried out
IUPAC nomenclature. using iron as a catalyst. The function of
H3CH2C CH3 iron in this reaction is to produce
A. Bromine free radicals
H3C CH2CH3
B. Bromide ions
A. Trans-3,4-dimethyl-2-hexene
C. Nucleophiles
B. Cis-3,4-dimethyl-3-hexene
D. Electrophiles
C. Cis-3,4-dimethyl-2-hexene
D. Trans-3,4-dimethyl-3-hexene
12. When benzene is treated with a
nitrating mixture, nitrobenzene is
8. According to Saytzeff’s rule, the most
formed.
stable alkene is NO2
conc. H2SO4
A. H2C CH CH3 + conc. HNO3

B. (H3C)2C C(CH2CH3)2
Which of the following statements is
C. H3CHC CHCH3
CORRECT concerning nitration?
D. H2C CH2
A. Nitration of benzene proceeds by
electrophilic addition.
9. An organic compound P undergo B. Nitration of benzene proceeds by a
hydrogenation reaction. P also reacts free radical mechanism.
witrh HCl to form 2-chlorobutane. C. The electrophile that attacks the
Determine the structure of P. benzene ring is the NO2+ ion.
A. CH3C(CH3)=CH2 D. The electrophile that attacks the
B. CH3CH2CH=CH2 benzene is NO2 molecule.
C. CH3CH=CH2
D. CH3CH2CH(OH)CH3 13. Which of the following statment is
correct about 2-methyl-2-propanol.

10. Which of the following reagents can be A. Is a secondary alcohol.

used to distinguish between alkane and B. Can be oxidised to ketone.

alkene? C. Reacts rapidly with Lucas reagent

A. Hydrogen at room temperature.

B. Chlorine water D. Produce yellow precipitate when

C. Br2 in CH2Cl2 reacted with alkaline iodine

D. Potassium manganate (VII) in solution.

NaOH (aq).

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14. Which of the following compound is an 17. An organic compound, X, has the
aromatic alcohol? following properties.
A. CH3CH(OH)CH2CH3 (i) It decolourise acidified KMnO4
B. upon heating.
OH
(ii) It forms a yellow precipitate
CH3
with an alkaline iodine
C.
solution.
OH
The structure of X is likely to be
D.
H3C OH
A. CH3COCH3
CH3 B. C(CH3)3(OH)
C. C6H5CH(OH)CH3
D. C6H5CHO
15. Compound 2-propanol can be oxidised
to propanone by using hot acidified
18. Name the carbonyl compound below
KmnO4 solution. Which of the
according to IUPAC nomenclature.
following reagents can be used to
confirm that oxidation has occured in O

this reaction?
A. 2,4-dinitrophenylhydrazine A. 3,3-dimethyl-4-phenyl-2-butanone
B. Tollens’ reagent B. 4-phenyl-3,3-dimethyl-2-butanone
C. Fehling’s solution C. 3-benzyl-3,3-methyl-2-butanone
D. Hydrogen cyanide D. 1-phenyl-3,3-dimethyl-2-butanone

16. Which of the following reagents can be 19. Compound X has the molecular
used to differentiate between propanal formula of C3H6O2. Compound X can
and propanone? undergo esterification but cannot be
A. 2,4-dinitrophenylhydrazine oxidised. Compound X may be,
B. Hydrogen cyanide A. CH3CO2CH3
C. Lithium tetrahydridoaluminate (III) B. CH3CH(OH)CHO
D. Tollens’ reagent C. CH2=CHCH2OH
D. CH3CH2CO2H

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20. Which of the following compound is a 1 A B C D
carboxylic acid?
2 A B C D
A. HCOOCH3
3 A B C D
B. HOOCCH2CH3
C. CH3COCOCH2CH3 4 A B C D
D. C6H5COCH3 5 A B C D

6 A B C D

7 A B C D

8 A B C D

9 A B C D

10 A B C D

11 A B C D

12 A B C D

13 A B C D

14 A B C D

15 A B C D

16 A B C D

17 A B C D

18 A B C D

19 A B C D

20 A B C D

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SECTION B

1. Give the IUPAC nomenclature for the following alkanes. [2M]

(a) CH2 (b) CH3 Cl
H2C CH(CH2CH3)
H3C C C CH3
H2C CH(CH2CH3)
CH2 Cl CH3

2. Compound B is a saturated hydrocarbon with a molecular formula C2H6. Compound B

gives only a single monobrominated product C, upon reaction with bromine liquid in the
presence of ultraviolet (UV) light.
a. Write the structural formulae of compound B and C. [2M]
b. Write the mechanism for the formation of compound C. [6M]

3. Define
a. Markovnikov’s rule [1M]
b. Saytzeff’s rule [1M]

4. Dehydration of 2-methyl-2-butanol gives a number of isomeric alkenes.

a. Draw the structural formula of 2-methyl-2-butanol. [1M]
b. Give the suitable reagent and condition that can be used for the dehydration of 2-
methyl-2-butanol. [1M]
c. Draw the structures of all isomeric alkenes formed. [2M]
d. Based on your answer in questions 4(c), indicate the major product of the dehydration
reaction. [1M]

5. Reaction of alkene Z are shown in the scheme below.

CH2CH3 Cl2, CH2Cl2
HBr
A H2C C B

CH2CH2CH3

H2O, H3O+

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 a. Draw the structural formulae of A, B and C. [3M]
b. State the observation and write the chemical equation when Z reacts with cold alkaline
KMnO4 solution. Give the name of this test. [3M]

6. Draw the condensed structure of the following alkenes. [3M]

a. 2-ethylhex-1-ene b. 4-methylcyclohexene

c. cis-2-pentene

7. Consider the following reaction scheme.

OH

alkene H3CH2C C CH2CH3

CH3
F

a. Give the IUPAC name for F. [1M]

b. Suggest one possible alkene to produce F and give suitable reagent for the conversion
of the corresponding alkene to alcohol F. [2M]
c. Name a chemical test to differentiate between 1-pentanol, 2-pentanol and F. State all
the observation. [4M]

8. Shows how propanone can be converted from propene. Include chemical equations,
reagents and condition in your answer. [5M]

9. Based on the reaction scheme below

OH O CH3

KMnO4, H+
A C


Na

a. Draw the structure of compound A and B. [2M]

b. State the reagent and condition in reaction C. [1M]
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10. Compound H and J below are examples of carbonyl compounds.
O O

CH3 H

H J
a. Give the IUPAC name for compound H and J. [2M]
b. Explain why H reacts with an alkaline solution of iodine whereas J does not. Write
the chemical equation for the reaction. [2M]

11. Indicate the reagents needed for the following conversions:

a. 2-butanol to butanone. [1M]
b. Butanone to 2-hydroxy-2-cyanobutane. [1M]

12. Based on the reaction scheme below, suggest reagent A to C. [3M]

O
A B
CH3CH2CH(OH)CH3 CH3CH2C(CN)(OH)CH3
C
H3CH2C CH3

-
CH3CH2COO + CHI 3

13. Suggest a test that can be used to distingush propanal and propanone. Include the name of
the test, equations and observations in your answer. [5M]

14. Aromatic compound X (C8H8O) is an oxidation product of compound Y (C8H10O). Both

X and Y yields iodoform when reacted with alkaline iodine solution. Give reasons and
determine the structural formulae of both X and Y. [5M]

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