Topic 10,20 – Organic Chemistry (Paper 1 Review)

1. What product results from the reaction of CH2==CH2 with Br2?

A. CHBrCHBr
B. CH2CHBr
C. CH3CH2Br
D. CH2BrCH2Br
2. What is the final product formed when CH3CH2OH is refluxed with acidified potassium dichromate(VI)?
A. CH3CHO
B. CH2==CH2
C. CH3COOH
D. HCOOCH3
3. Which of the substances below is least soluble in water?
A. CH2OHCHOHCH2OH
O
B.
CH 3 CCH 3
C.
O
D.
CH 3 COCH 3
4. Which formulas represent butane or its isomer?
I. CH3(CH2)2CH3
II. CH3CH(CH3)CH3
III. (CH3)3CH
A. I and II only
B. I and III only
C. II and III only
D. I, II and III

5. Which compound can exist as optical isomers?

A. CH3CHBrCH3
B. CH2BrCHBrCH3
C. CH2BrCHBrCH2Br
D. CHBr2CHBrCHBr2

6. Which statement about the reactions of halogenoalkanes with aqueous sodium hydroxide is correct?
A. Primary halogenoalkanes react mainly by an SN1 mechanism.
B. Chloroalkanes react faster than iodoalkanes.
C. Tertiary halogenoalkanes react faster than primary halogenoalkanes.
D. The rate of an SN1 reaction depends on the concentration of aqueous sodium hydroxide.

7. Which statement about neighbouring members of all homologous series is correct?

A. They have the same empirical formula.
B. They differ by a CH2 group.
C. They possess different functional groups.
D. They differ in their degree of unsaturation.

8. Which type of compound must contain a minimum of three carbon atoms?

A. An aldehyde
B. A carboxylic acid
C. An ester
D. A ketone

9. Which compound can exist as optical isomers?

A. H2NCH2COOH
B. CH2ClCH2Cl
C. CH3CHBrI
D. HCOOCH3

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10. Which product is formed by the reaction between CH2CH2 and HBr?
A. CH3CH2Br
B. CH2CHBr
C. BrCHCHBr
D. CH3CHBr2
11. Which reaction(s) involve(s) the formation of a positive ion?
–
I. CH3CH2CH2Br + OH
–
II. (CH3)3CBr + OH
A. I only
B. II only
C. Both I and II
D. Neither I nor II
12. Which compound has the lowest boiling point?
A. CH3CH2CH(CH3)CH3
B. (CH3)4C
C. CH3CH2CH2CH2CH3
D. CH3CH2OCH2CH3
13. Which species will show optical activity?
A. 1-chloropentane
B. 3-chloropentane
C. 1-chloro-2-methylpentane
D. 2-chloro-2-methylpentane
14. What type of reaction does the equation below represent?
CH2=CH2 + Br2 → BrCH2CH2Br
A. substitution
B. condensation
C. reduction
D. addition

15. Consider the following compounds.

I. CH3CH2CH(OH)CH3
II. CH3CH(CH3)CH2OH
III. (CH3)3COH

The compounds are treated separately with acidified potassium dichromate(VI) solution. Which will produce a
colour change from orange to green?
A. I and II only
B. I and III only
C. II and III only
D. I, II and III

16. Which compound reacts most rapidly by a SN1 mechanism?

A. (CH3)3CCl
B. CH3CH2CH2CH2Br
C. (CH3)3CBr
D. CH3CH2CH2CH2Cl

17. Which compound is a member of the same homologous series as 1-chloropropane?

A. 1-chloropropene
B. 1-chlorobutane
C. 1-bromopropane
D. 1,1-dichloropropane

18. What is the organic product of the reaction between ethanol and ethanoic acid?
A. CH3CHO
B. CH3COOCH3
C. CH3CH2COOCH3
D. CH3COOCH2CH3
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19. Which statement is correct about the reaction between methane and chlorine?
–
A. It involves heterolytic fission and Cl ions.
B. It involves heterolytic fission and Cl radicals.
–
C. It involves homolytic fission and Cl ions.
D. It involves homolytic fission and Cl radicals.

20. Which formula is that of a secondary halogenoalkane?

A. CH3CH2CH2CH2Br
B. CH3CHBrCH2CH3
C. (CH3)2CHCH2Br
D. (CH3)3CBr

21. Which compound is converted to butanal by acidified potassium dichromate(VI) solution?

A. butan-1-ol
B. butan-2-ol
C. butanone
D. butanoic acid

22. Which compound can exist as optical isomers?

A. CH3CHBrCH3
B. CH2ClCH(OH)CH2Cl
C. CH3CHBrCOOH
D. CH3CCl2CH2OH

23. Which type of compound can be made in one step from a secondary alcohol?
A. an aldehyde
B. an alkane
C. a carboxylic acid
D. a ketone

24. Which reaction type is typical for halogenoalkanes?

A. nucleophilic substitution
B. electrophilic substitution
C. electrophilic addition
D. nucleophilic addition

25. Which substance is not readily oxidized by acidified potassium dichromate(VI) solution?
A. propan-1-ol
B. propan-2-ol
C. propanal
D. propanone

26. Propane, C3H8, undergoes incomplete combustion in a limited amount of air. Which products are most likely to be
formed during this reaction?
A. Carbon monoxide and water
B. Carbon monoxide and hydrogen
C. Carbon dioxide and hydrogen
D. Carbon dioxide and water

27. Which are characteristics typical of a free radical?

I. It has a lone pair of electrons.
II. It can be formed by the homolytic fission of a covalent bond.
III. It is uncharged.
A. I and II only C. I, II and III
B. I and III only D. II and III only

28. Which of the following products could be formed from the oxidation of ethanol?
I. ethanal
II. ethanoic acid
III. ethane
A. I and II only C. II and III only
B. I and III only D. I, II and III
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29. What is the reaction type when (CH3)3CBr reacts with aqueous sodium hydroxide to form (CH 3)3COH and NaBr?
A. Addition
B. Elimination
C. SN1
D. SN2

30. Which species is a free radical?

A. •CH3
+
B. CH3
–
C. CH3
D. :CH3
31. Nylon is a condensation polymer made up of hexanedioic acid and 1,6-diaminohexane.
Which type of linkage is present in nylon?
A. Amide
B. Ester
C. Amine
D. Carboxyl

32. How many chiral carbon atoms are present in a molecule of glucose?

A. 1
B. 2
C. 3
D. 4

33. An organic compound X reacts with excess acidified potassium dichromate(VI) to form compound Y, which reacts
with sodium carbonate to produce CO2(g).
What is a possible formula for compound X?
A. CH3CH2COOH
B. CH3CH2CH2OH
C. CH3CH(OH)CH3
D. (CH3)3COH
34. Which products can be potentially obtained from crude oil and are economically important?
I. Plastics
II. Margarine
III. Motor fuel
A. I and II only
B. I and III only
C. II and III only
D. I, II and III
35. What is the product of the following reaction?
CH3CH2CH2CN + H2 
Ni

A. CH3CH2CH2NH2
B. CH3CH2CH2CH3
C. CH3CH2CH2CH2CH3
D. CH3CH2CH2CH2NH2
36. What is the correct IUPAC name for the following compound?
CH 3 CHCH 2 CH 2 CN

CH 3
A. 4-methylbutanenitrile
B. 4-methylpentanenitrile
C. 2-methylbutanenitrile
D. 2-methylpentanenitrile
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ANSWERS

1. D
2. C
3. D
4. D
5. B
6. C
7. B
8. D
9. C
10. A
11. B
12. B
13. C
14. D
15. A
16. C
17. B
18. D
19. D
20. B
21. A
22. C
23. D
24. A
25. D
26. A
27. D
28. A
29. C
30. A
31. A
32. D
33. B
34. D
35. D
36. B