REVISION SET 3

CHEMISTRY DK024

SECTION A

1. The molecule of 2-methylpropane has 4. Based on the chemical equation below,

the structure below. Br
CH2Cl2
H + Br2
H H
C Br
H H A
H C
Cx C H
H H
What is the type of reaction involve in
C
H H the synthesis of compound A?
H

The carbon atom labelled x is a A. Elimination

A. Primary carbon atom B. Substitution

B. Secondary carbon atom C. Addition

C. Tertiary carbon atom D. Rearrangement

D. Quaternary carbon atom

5. Which of the following compound has

2. The skeletal formula of an organic the highest boiling point?

compound is as shown. What is the A. (CH3)2CHCH3

name of the homologous series to B. CH3(CH2)2CH3

which the compound belongs? C. CH3(CH2)3CH3

Cl Cl D. (CH3)2CHCH2CH3

6. Two alkyl groups bonded to carbon

A. Ether
marked * in the molecule shown below
B. Nitrile
are
C. Acyl halide
I
D. Haloalkane CH(CH3) 2
H3C C* CH3
3. How many possible isomers are there CH(CH3)CH2CH3
II
for a compound with a molecular
formula of C5H12. I II

A. 3 A. propyl butyl

B. 4 B. isopropyl sec-butyl

C. 5 C. isopropyl tert-butyl

D. 6 D. propyl isobutyl

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7. Which of the following is the structural 11. The following reaction is known as
formula for cis-3-hexene? CH3
AlCl3

A. H CH2CH3 + CH 3Cl
C C
H3CH2C H A. Friedel-crafts acylation
B. H CH2CH2CH3
B. Nucleophilic substitution
C C
H3C H
C. Friedel-crafts alkylation
H H D. Coupling reaction
C.
C C
H3CH2C CH2CH3
12. Which of the following compound is
D. H H
C C (chloromethyl)benzene?
H3C CH2CH2CH3 A. CH2Cl

8. The major product of

B. CH3
hydrobromination reaction of 3-
methyl-1-pentene is,
A. 1-bromo-3-methylpentane Cl

B. 2-bromo-3-methylpentane C. CH3
Cl
C. 3-bromo-3methylpentane
D. 4-bromo-2-methylpentane

D.
9. Which of the following molecule is H3C Cl

NOT possibly an alkene?

A. C2H2
B. C4H8 13. What is the name of the process where
C. C4H6 ethanol is prepared from glucose?
D. C6H8 A. Oxidation
B. Hydrolysis
10. What is the type of reaction when C. Reduction
cyclohexene reacts with chlorine D. Fermentation
without any UV light present?
A. Free radical substitution
B. Nucleophilic substitution
C. Electrophilic substitution
D. Electrophilic addition
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14. The reagent that can be used to 17. Which of the following compounds
differentiate 1-propanol and 2- will forms a yellow precipitate when
propanol is, reacted with Brady’s reagent.
A. Cl2 (excess), NaOH A. CH3COCH2CH3
B. 2,4-dinitrophenylhydrazine B. CH3COOCH3
C. HCl (conc), ZnCl2 C. CH3CONH2
D. Silver diamine complex solution D. CH3COCl

15. An organic compound, W, forms a 18. Which of the following compounds

yellow precipitate with alkaline iodine undergoes nucleophilic addition with
solution, but does not react with HCN?
[Ag(NH3)2]+ soluiton. Compound W A. CH2=CH2
may be, B. CH3CH2COOH
A. CH3CHO C. CH3CH2Cl
B. CH3CH2CH2COCH3 D. CH3CH2COCH3
C. CH3CH3COCH2CH3
D. CH3CH2CHO 19. The IUPAC name for the following
carboxylic acid is
16. Which of the following statement is O

TRUE for compound Y below

OH
O
A. 3-methylbutanoic acid
B. 2-methylbutanoic acid
C. 3,3-dimethylpropanoic acid
A. It is a saturated compound.
D. 4-methylbutanoic acid.
B. It is an aromatic compound.
C. Its molecular formula is C6H5O
20. Which of the following alcohol can be
D. It gives yellow precipitate when
oxidised to 2,3-dimethylpentanoic
reacted with Brady’s reagent.
acid?
A. 3,3-dimethyl-2-pentanol
B. 2,3-dimethyl-1-pentanol
C. 3,3-dimethyl-1-pentanol
D. 2,3-dimethyl-2-pentanol

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SECTION B
1. Write the IUPAC nomenclature for the following alkane. [1M]
Cl Br
H3C C C CH3
Br Cl

2. Combustion of alkanes in air gives non-poisonous and non-polluting products,

depending on the condition in which the combustion takes place. Write the chemical
equations when hexane reacts in
a. Excess oxygen [1M]
b. Limited oxygen [1M]

3. Arrange the following alkanes in order of increasing boiling point. Explain your
answer. [5M]
2,2-dimethylheptane, 4-ethylheptane, 2,2,4,4-tetramethylpentane and nonane

4. Name the following alkene according to IUPAC nomenclature. [3M]

a. CH2CH3
H3C CH2 C CH2 CH3
H

b. H CH2CH3
C C
H3C H

c.

5. Compound C reacts with reagent D to give unsaturated compounds, E and F.

CH3
OH D
E + F

compound C

a. Draw the structure of E and F. [2M]

b. Label the major product. [1M]
c. State reagent D. [1M]
d. State the rule used to determine the major product from the reaction above. [1M]

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6. Suggest a test to distinguish between methylcyclohexane and 1-methylcyclohexene.
Include the name of test, equations and observations in your answer. [5M]

7. Based on the chemical equation below,

H3C H
C C + HCl F
H3C CH2CH3

a. Give the structure of F. [1M]

b. State the type of reaction. [1M]
c. Name compound F. [1M]
d. State the rule used to determine the structure of F. [1M]

8. Based on the structure of W, X, Y and Z below:

CH3CH(CH3)CH2OH CH3C(CH3)(OH)CH 3 CH3CH(OH)CH3 CH3CH2CH2CH2OH
W X Y Z

a. Choose a compound that turns cloudy immediately when reacted with Lucas
reagent. Give a reason and write the chemical equations involved. [3M]
b. Which compound gives a yellow precipitate upon reaction with alkaline iodine
solution? Write the chemical equation involved. [2M]

9. Deduce the structure and name of compound K, L and M based on the following
observations.
a. Alcohol K, C4H9OH does not show any changes when Lucas reagent is added but
it react with KMnO4, H+ to form 2-methylpropanoic acid. [2M]
b. Alcohol L, C4H10O gives positive result with iodine in base. [2M]
c. Alcohol M, C5H12O immediately turn cloudy when Lucas reagents is added, but
does not show any changes with acidified potassium dichromate (IV). [2M]

10. Predict which of the compound in each of the following pairs is more soluble in water.
a. Propane and 1-propanol. [1M]
b. 1-propanol and 1,2-propanediol [1M]
c. 2-propanol and 2-pentanol [1M]

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11. Draw the structure of the following carbonyl compound. [4M]
a. 2-ethyl-4-methylpentanal
b. Phenylethanal
c. Phenylethanone
d. 1-cyclopropyl-1-propanone

12. Compound A, B and C are isomers with a molecular formula of C4H8O. When
compound A, B and C react with 2,4-dinitrophenylhydrazine, an orange precipitate is
formed. Compound B and C give positive result with silver nitrate in aqeous ammonia.
Deduce the structural formula for A, B and C. Explain your answer. [6M]

13. Based on the reaction scheme below:

I2 (excess), NaOH (aq)

OH
KMnO4, H+ H2O, H3O+
H3C C CH3 A C

H
KCN, H3O+

D
a. Draw the structure of A, B, C and D. [4M]
b. Give the name for carbonyl compound A. [1M]
c. Suggest a test that can confirm the formation of compound A. [1M]

14. Write a balanced chemical equation for each of the following reactions.
a. Benzaldehyde is reacted with acidified KMnO4. [1M]
b. Propanone is reacted with iodine in a basic solution. [1M]
c. Ethanal is reacted with 2,4-dinitrophenylhydrazine. [1M]

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