REVISION SET 4

CHEMISTRY DK024

SECTION A

1. Which of the following statements is 4. Classify the carbons labelled x, y and z

NOT TRUE for organic compound? as 1o, 2o or 3o carbon atoms.
A. They are covalent molecules. x
H3C CH2
B. The main source is petroleum and CH CH3
z
natural gas. H3C
y
C. They may exist as simple or
x y z
complex molecules.
A. 1o 3o 2o
D. Carbon dioxide is an example of
B. 2o 3o 1o
simplest organic compound.
C. 2o 1o 3o
D. 3o 2o 1o
2. Which of the following molecules is
not an isomer of CH3COCH2CH3?
5. Name the following alkane.
A. CH3CH2OCH2CH3
CH3C(CH3)2CH2CH2CH2C(CH3)2CH3
B. CH3CH2CH2CHO
A. 2,2,5,6-tetramethylheptane
C. CH2=CHCH(OH)CH3
CH2
B. 2,2,6,6-tetramethylheptane
D.
H2C CHCH2OH C. 1,1,2,5,5-pentamethylhexane
D. 2,2,5,6,6-pentamethylhexane

3. Which of the following structure

6. The reaction of cyclohexane with
represents an ester?
chlorine in the presence of light is a
A. OH
A. Electrophilc addition
O
B. Electrophilic substitution
B. O O
C. Free radical substitution
D. Free radical addition

C. CH3CH2COOCOCH3
D. C6H5COC6H5

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7. Name the following alkene. 10. Several reagent were reacted with 2-
H3C CH2 CH3 methyl-2-pentene. Which of the
C C
following products is NOT correct?
H3C CH3
Reagent Product
A. 3,4-dimethyl-3-pentene
A. H2, Ni Hexane
B. 2,3-dimethyl-2-pentene
B. Br2 in CH2Cl2 2,3-dibromo-2-
C. 3,4-dimethyl-1-pentene
methylpentane
D. 2,3-dimethyl-1-pentene
C. HBr 2-bromo-2-
methylpentane
8. The major product of dehydration of 2-
D. H2O, H3O+ 2-methyl-2-
butanol is,
pentanol
A. 1-butene
B. 2-butene
11. Which of the following is a primary
C. 2-methylpropene
alcohol?
D. Propene
A. C6H5OH
B. CH3CH(OH)CH3
9. Which of the following reagents can be
C. CH3CH(OH)CH2CH3
used to carry out the following
D. CH3CH=CHCH2CH2OH
conversion?
H3C C6H5 H C6H5
C C H3C C C H 12. The correct structure for 2-methyl-2-
H3C CH3 CH3 CH3 butanol is
A. LiAlH4 in dry ether, 30oC A. OH CH3 H
H3C C C C H
B. Zn, HCl, 200oC
H H CH3
C. H2 gas, platinum, 200oC
B. OH H
o
D. H2 gas, carbon, 300 C. H3C C C CH3
CH3 H

C. OH H H
H C C C H
CH3 H CH3

D. H OH
H C C CH3
CH2 H
H3C

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13. Toluene is prepared from benzene and 16. Name the type of reaction involve to
bromomethane in the presence of form compound X.
iron(III) bromide. Which of the O OH

following is involved in this reaction?

+ HCN H3C CH3
H3C CH3
CN
A. Br+ X
-
B. Br A. Nucleophilic substitution
+
C. CH3 B. Electrophilic addition
-
D. CH3 C. Nucleophilic addition
D. Electrophilic substitution
14. Which of the following compound
below is aromatic? 17. Compound K reacts with the test below
A. Test Observation
Triiodomethane Yellow
B.
precipitate
2,4-DNPH Orange
C. precipitate
Which of the following compound
D. below best represent the structure of
compound K?
A. CH3CH2CHO
B. CH3CH2OH
15. Which of the following molecular
C. CH3CH2COCH3
formula represent carbonyl compound?
D. CH3CH2COCH2CH3
A. C4H10O
B. C4H8O
18. Suggest a suitable test that CANNOT
C. C4H8O2
be used to distinguish between
D. C4H8
propanal and propanone.
A. HCl (conc), ZnCl2
B. Alkaline iodine solution
C. Silver diamine complex solution
D. Fehling’s test

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19. The ester below can be prepared 1 A B C D
between
2 A B C D

3 A B C D
O O
CH2 C
4 A B C D
CH3

A. O 5 A B C D
CH2 and
H3C Cl
OH 6 A B C D
B. O
OH and 7 A B C D
H3C OH

C. O 8 A B C D
OH and
H3C Cl
9 A B C D
D. O
CH2 and 10 A B C D
OH H5C2 OH

11 A B C D

12 A B C D
20. What is the name of the following
compound? 13 A B C D
H
14 A B C D
H3C C CH2
OH C O
15 A B C D
HO

A. 1-carboxylbutanol 16 A B C D
B. 1-carboxylbutan-2-ol
17 A B C D
C. 3-hydroxybutanoic acid
18 A B C D
D. 1,3-dihydroxybutanal
19 A B C D

20 A B C D

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SECTION B

1. Petrol is a complex mix of light hydrocarbons which are mostly branched-chain alkanes.
Petrol with octane number 95 contains 95% 2,2,4-trimethylpentane. This compound can be
obtained by breaking up large hydrocarbon molecule such as dodecane, C12H26 using a
catalyst such as zeolite.

+
2,2,4-trimethylpentane A
dodecane

(a) Name the process where a large hydrocarbon molecule is broken into smaller hydrocarbon
molecules. [1M]
(b) Draw the structure of hydrocarbon A. [1M]
(c) Name hydrocarbon A. [1M]
(d) Write an equation for the complete combustion of 2,2,4-trimethylpentane. [2M]

2. Cyclohexane and chlorine react to form dichloromethane under sunlight.

(a) Name the type of reaction involve in this reaction. [1M]
(b) Write equations to show the propagation steps in the formation of dichloromethane. [2M]

3. The skeletal formula of an unsaturated hydrocarbon Q is shown below.

Q
(a) Draw the condensed structural formula of the compound. [1M]
(b) Name compound Q according to the IUPAC nomenclature. [1M]
(c) Draw the structural formula of product formed when Q reacts with:
i. Bromine in CCl4 [1M]
ii. HCl [1M]
(d) Compound Q can be hydrated by adding concentrated sulphuric acid, followed by
hydrolysis.
i. Draw the structure of product formed. [1M]
ii. State the rule used to determine the structural formula of the product. [1M]

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4. Draw the expanded structural formula for the following alkenes. [4M]
(a) cis-2-butene
(b) 1,4-dimethylcyclopentene
(c) 4-chloro-1-methylcyclobutene
(d) 3-isopropyl-2-hexene

5. Draw the structural formula of A – E. [5M]

Br2, CH2Cl2
A

H HCl
B
C CH3
C H2O, H3O+
C
CH3
H2, Ni
D
-
KMnO4, OH , dilute
E
cold

6. Write the observations for each of the following reaction. [2M]

(a) 5 drops of bromine in inert solvent was added to butane and the mixture was then exposed
to sunlight.
(b) 3ml of cold, dilute and alkaline potassium manganate (VII) solution was added to 3-
hexene.

7. When a person consumes alcohol, the alcohol gets into the blood by absorption through the
stomach wall. Some self-test breath analyser kits estimate the amount of alcohol in blood.
When ethanol reacts with acidified potassium dichromate (VI) in the breath analyser, ethanol
is oxidised to ethanoic acid and dichromate (VI) ion is reduced to chromium (III) ion.
(a) Draw the structure of ethanoic acid formed. [1M]
(b) If alcohol is present, what is the change in the colour of the dichromate (VI) solution. [1M]
(c) What is the product formed if the oxidation of ethanol is incomplete. [1M]

8. Compound A, C4H10O reacts with sodium to produce a combustible gas. When A is heated
with acidified KMnO4, carbonyl compound B is formed. Both A and B form a yellow
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 precipitate when reacted with an alkaline solution of iodine. Suggest a possible identity of A
and B. Explain your reasoning and give equation where appropiate. [6M]

9. Arrange the following compound in order of increasing boiling point. Include explanation in
your answer. [5M]

1,3-hexanediol; octane; 1-heptanol

10. Name the following aldehydes and ketones using the IUPAC nomenclature. [6M]

(a) O (b) H
H3C C CH2CHO
OH

CH3

(c) CHO (d) O

CH3
CH3 C
H3C CH2CH2CH(Cl)CH3

(e) O (f) O

C C Cl
H3C H

11. An organic compound X, C5H12O, forms a yellow precipitate when tested with 2,4-
dinitrophenylhydrazine. X reduces Tollen’s reagent but X does not form any precipitate with
alkaline iodine solution.
(a) What functional group is present in X. [1M]
(b) What does the negative test with alkaline iodine indicate? [1M]
(c) Draw the structural formula of X if structure X have quaternary carbon. Give the IUPAC
name for X. [2M]
(d) Write separate equations for the reaction between X and
i. 2,4-dinitrophenylhydrazine [2M]
ii. Tollen’s reagent [2M]

12. Suggest a chemical test to distinguish between CH3COCH3 and CH3CH2COCH2CH3. [5M]

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