REVISION SET 1

CHEMISTRY DK024

SECTION A

1. In which of the following 3. Which of the following is the

compounds have a quaternary functional group of an aldehyde?
carbon atom? A. COOH
A. CH3CH2CH3 B. COCl
B. CH3CH(OH)CH2OH C. CHO
C. (CH3)3CCH2CH3 D. COC
D. C6H5COCH(CH3)2 4. Which compound is correctly
2. The structure of lactic acid is shown paired with its functional group?
below. Compound Functional
OH group

H C COOH A. alcohol -O-

B. Amine -NH2
CH3
C. Ketone -CHO
Which of the following shows the
D. Amide -CN
skeletal structure of lactic acid?
A. O

O
5. Which of the following is most
probably a cyclic alkane?
O A. C4H10
B. OH B. C5H10
C. C6H10
COOH D. C6H6
C. OH

OH

D. OH

OH

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6. What is the name of the following 9. Several reagents were reacted with
alkane? pent-2-ene. Which of the following
H3C CH2 CH3 products is not correct?
CH CH2
Reagent Product
CH3
A. Dilute Pentane-1,2-
A. 2-methylpentane
H2SO4 diol
B. 3-methylpentane
B. H2, Ni Pentane
C. 4-methylpentane
C. Excess 1,2-
D. 2,2-dimethylbutane
Br2 dibromopentane
D. HBr 2-

7. The IUPAC name for the following bromopentane

compound is
H H 10. Which of the following will be
formed when cyclohexene reacts
H H
with cold, alkaline KMnO4?
H H OH
I II
H H COOH
OH

A. Cyclopentene
B. Pent-1-ene OH

C. Pent-2-ene III

D. Pent-3-ene
A. I only
B. I and II only
8. What is the type of reaction when
C. II and III only
cyclohexene reacts with chlorine
D. I, II and III
without any ultraviolet light
present?
11. What is the IUPAC name for the
A. Free radical substitution
following compound?
B. Nucleophilic addition
Cl
C. Electrophilic substitution
D. Electrophilic addition
OH

A. 3-chlorophenol
B. 3-hydroxychlorobenzene
C. 1-hydroxychlorobenzene
D. 3-chloro-1-hydroxybenzene

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12. Why does benzene undergo 15. Which of the following is an
substitution reactions rather than aldehyde?
addition reactions? A. O

A. Benzene is a planar, aromatic C

H H
compound.
B. O
B. All the carbon atoms in benzene
is sp2 hybridised. C
H3C O CH3
C. All the carbon-carbon bonds in
C. O
benzene is strong.
C
D. Benzene has extra stability due H3CH2C C6H5
to the delocalized π electrons. D. O

C
H3CH2C O CH3
13. Which of the following compounds
is an aromatic alcohol?
16. Which of the following alcohols can
A. C6H5COOH
be oxidized to 2-methylpentan-3-
B. C2H5OCH3
one?
C. C6H5CH(OH)CH3
A. CH3CH2CH(OH)CH3
D. CH3-C6H4-OH
B. CH3CH(OH)CH2CH2CH3
C. (CH3)3CCH(OH)CH3
14. Which of the following compounds
D. (CH3)2CHCH(OH)CH2CH3
is expected to have the highest
boiling point?
17. Which of the following reagents can
A. CH3CH2CH2OH
be used to test the present of
B. CH2OHCH2OH
aldehyde?
C. CH3CH2CH(OH)CH3
A. Alkaline iodine
D. (CH3)2CHCH2CH2OH
B. Acidified KMnO4
C. Ammonical silver nitrate
D. Silver diamine complex.

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18. What is/are the name(s) of the
following compound?
1 A B C D
O
2 A B C D
C
H C6H5
3 A B C D
I Cyclohexylmethanal
4 A B C D
II Benzaldehyde
III phenylmethanal 5 A B C D
A. I only 6 A B C D
B. I and II only
7 A B C D
C. II and III only
D. I, II and III 8 A B C D
19. Which of the following alcohol can 9 A B C D
be oxidised to 2-methylpropanoic
10 A B C D
acid?
A. 2-methylpropan-1-ol 11 A B C D

B. 2-methylpropan-2-ol 12 A B C D
C. Butan-2-ol
13 A B C D
D. 2-methylbutan-2-ol
20. What is the name of the following 14 A B C D

compound? 15 A B C D
H3C CH2 O
CH C 16 A B C D

OH OH 17 A B C D
A. 1-carboxylbutanol
18 A B C D
B. 1-carboxylbutan-2-ol
19 A B C D
C. 3-hydroxybutanoic acid
D. 1,3-dihydroxybutanal 20 A B C D

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SECTION B

1. Arrange the following compound in the order of increasing boiling point. Explain your
answer. [5M]
Propane; Methane; Pentane; Heptane

2. Write the mechanism for the reaction between ethane with chlorine in CH2Cl2 under
UV light. [7M]

3. Write the structural formula for each of the following alkenes. [4M]

a. Trans-2-butene b. 2,3-dimethylpent-2-ene
c. 2-methylbuta-1,3-diene d. 2,3-dimethylcyclobutene

4. Suggest a chemical test that can be used to differentiate between compound T and U
below. [5M]
CH3 CH3

T U
5. A hydroxyl compound 2-methyl-2-butanol undergoes dehydration to give major
product J and minor product K.
(a) Draw the structure of 2-methyl-2-butanol. [1M]
(b) Give the structure of J and K. [2M]
(c) State the law applied in determining the major product. [1M]
(d) Name the compound J. [1M]

6. Give the structure of compound M and N. [2M]

(a) CH3

+ HBr M

CH3
(b) OH-, dilute
+ KMnO 4 N
CH3
cold

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7. Give the IUPAC name for the following alcohols. [2M]
(a) (b) H3CH2CH2C CH2 Cl
CH CH2
OH
OH

8. By using iodoform test, shows how alcohol K and L can be distinguishing in laboratory.
Include chemical equations and observation for your answer. [3M]
OH CH3

H3C HC H3CH2C C OH
CH3 CH3
K L

9. Compound A and B are isomer with a molecular formula of C5H12O. The reaction of A
and B with sodium metal forms gas bubbles. When both A and B react with chromic
acid, only A forms a green solution whereas B does not. Compound A turn cloudy
within 5-10 minutes after the addition of Lucas’s reagent.
(a) State the functional group exists in A and B. [2M]
(b) Draw the structure of A and B. [2M]

10. Glycerol is a colourless, odourless, and viscous sweet-tasting liquid that is highly
soluble in water. It is widely used in pharmaceutical formulations. Glycerol is also used
as a sugar substituted. The structural formula of glycerol is
H OH H
H C C C OH
OH H H
glycerol

(a) What is the IUPAC name for glycerol? [1M]

(b) Explain the high solubility of glycerol in water. [2M]
(c) Draw the structural formula of the product formed when glycerol is reacted with
acidified sodium dichromate. [1M]

11. Shows how 1-butanol can be converted into butanoic acid. [2M]

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12. Name the following carbonyl compounds. [6M]
(a) CHO (b) H5C6H2C
O
H

(c) CH3CH(CH3)CH2CHO (d) O

(e) O (e) O
H3C C Cl
CH2 CH
CH3

13. The Tollens’ reagent can be used to differentiate between propanal, propanone and 1-
propanol. Write chemical equations and give the observation for each reaction involved.
[4M]

14. By using chemical equation, show the synthesis of butanal from 1-butanol. [2M]

15. Draw the structure of V, W, X Y and Z as shown in the following scheme. [5M]

V
Z
NaCN, H3O+
HCl (conc), ZnCl2
O
KMnO4, H+ C H2O, H3O+
Y H3CH2C CH3 W

excess I2, NaOH

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