Halogenoalkanes Qp. Answers - Multichoice

Halogenoalkanes Question Paper1
1 Which intermediate ion forms in the greatest amount during the addition of HBr to propene?A
A CH3CH+CH3
B CH3CH2CH2+
C CH3CH–CH2Br
D CH3CHBrCH2–
2 Coniine is the major constituent of the poison ‘oil of hemlock’.D
N CH2CH2CH3
H
coniine
Coniine can be synthesised by reacting ammonia with a dibromo compound, X.
NH3 + C8H16Br2 → coniine + 2HBr

X
What is the name of compound X?
A 1,1-dibromo-2-propylcyclopentane
B 1,2-dibromo-2-propylcyclopentane
C 1,4-dibromooctane
D 1,5-dibromooctane
3 2-bromopropane reacts with a hot concentrated solution of sodium hydroxide in ethanol. D
Which substance is the major product of this reaction?
A propan-1-ol
B propan-2-ol
C 2-hydroxypropene
D Propene
4. Which halogenoalkane will undergo an SN1 reaction and produce a yellow precipitate when
AgNO3(aq) is added to it? D
A 1-chlorobutane
B 1-iodobutane
C 2-chloro-2-methylpropane
D 2-iodo-2-methylpropane
5. The presence of a halogen in an organic compound may be detected by warming the
organic compound with aqueous silver nitrate.
Which compound would be the quickest to produce a precipitate? C
A B C D
Cl F F Cl
Cl Cl F Br
Cl F I F
6. The Finkelstein reaction occurs when NaI in propanone reacts with a chloroalkane or
bromoalkane. The halogen is directly replaced by I and the reaction only works for primary
halogenoalkanes.
Which halogenoalkane would produce compound X? D
compound X
A (CH3)2CHCH(CH3)CH2CH2Br
B (CH3)2CHCH(CH3)CH2Br
C (CH3)2CHCH2CH2CH(CH3)Cl
D (CH3)2CHCH2CH(CH3)CH2Cl
7. What is involved in the mechanism of the reaction between NaOH(aq) and 1-bromobutane A
A attack by a nucleophile on a carbon atom with a partial positive charge

B heterolytic bond fission and attack by a nucleophile on a carbocation
C homolytic bond fission and attack by an electrophile on a carbanion
D homolytic bond fission and attack by a nucleophile on a carbocation
•
8. When heated with chlorine, the hydrocarbon 2,2-dimethylbutane undergoes free radical
substitution. In a propagation step the free radical X is formed.
CH3
CH3+ Cl ●  X + HCl
●
CH3CH2 C
CH3
•
How many different forms of X are possible? D
A 1 B 2 C 3 D 4
9. A tertiary bromoalkanereacts with aqueous NaOH. The the reaction pathway below. C
Y
energy
extent of reaction
Which point in the diagram is correctly identified?
A X is C+
–
B X is HO C Br
C Y is C+
–
D Y is HO C Br
10. The hydrolysis of 1-chloropropane to produce propan-1-ol is much slower than the
corresponding hydrolysis of 1-iodopropane.B
Which statement explains this observation?
A Chlorine is more electronegative than iodine.

B The bond strength of the C – I bond is less than that of the C – Cl bond.
C The carbon atom in the C – Cl bond is more δ+ than that in the C – I bond.
D The hydrolysis involves a nucleophilic addition reaction.

11. Halogenoalkanes undergo a range of nucleophilic substitution reactions. Which reaction
proceeds only by an SN1 mechanism? D
A CH3CH2Br + NH3
B CH3CH2CH2I + OH–
C CH3CHBrCH3 + NH3
D (CH3)3CI + OH–
12. In the hydrolysis of bromoethane by aqueous sodium hydroxide, what is the nature of
the attacking group and of the leaving group? D
13. Nine compounds have molecular formula C4H8Br2.

Which compound may be synthesised from an alkene by an addition reaction? B
A 1,1-dibromobutane
B 1,2-dibromobutane
C 1,3-dibromobutane
D.1,3-dibromomethylpropane
14. Bromine reacts with ethene to form 1,2-dibromoethane.
What is the correct description of the organic intermediate in this reaction? D
A It has a negative charge.

B It is a free radical.
C It is a nucleophile.
D It is an electrophile
15. Four drops of 1-chlorobutane, 1-bromobutane and 1-iodobutane were put separately into
3 test-tubes of aqueous silver nitrate. A hydrolysis reaction occurred. (R is the butane chain
C4H9– and X the halogen atom.) H2O(l) + R–X(l) + Ag+(aq) → R–OH(aq) + AgX(s) + H+(aq)
The rate of formation of cloudiness in the tubes was in the order RCl < RBr < RI. Why is this?
A The R–X bond polarity decreases from RCl to RI.
B The solubility of AgX(s) decreases from AgCl to AgI.
C The ionisation energy of the halogen decreases from Cl to I.
D. The bond energy of R–X decreases from RCl to RI
16. Which term describes the action of NaOH(aq) on a bromoalkane? D
A acid-base reaction
B electrophilic substitution
C elimination of HBr
D nucleophilic substitution
17. Which fragment could appear in the chain produced by polymerising 1,1-dichloroethene? C
A – CH2– CH2– CCl 2 – CCl 2– CH2– CH2–

B – CHCl – CHCl – CHCl – CHCl – CHCl – CHCl –
C – CH2– CCl 2 – CH2– CH2– CH2– CCl 2 –
D – CCl 2 – CCl 2 – CH2– CH2– CH2– CCl 2 –
1 A 1 B
0
2 D 1 D
1
3 D 1 D
2
4 D 1 B
3
5 C 1 D
4
6 D 1 D
5
7 A 1 D
6
8 D 1 C
7
9 C

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Halogenoalkanes Question Paper1

Coniine can be synthesised by reacting ammonia with a dibromo compound, X.

NH3 + C8H16Br2 → coniine + 2HBr

What is the name of compound X?

3 2-bromopropane reacts with a hot concentrated solution of sodium hydroxide in ethanol. D

Which substance is the major product of this reaction?

Which compound would be the quickest to produce a precipitate? C

Which halogenoalkane would produce compound X? D

A attack by a nucleophile on a carbon atom with a partial positive charge

Which point in the diagram is correctly identified?

Which statement explains this observation?

A Chlorine is more electronegative than iodine.

D The hydrolysis involves a nucleophilic addition reaction.

13. Nine compounds have molecular formula C4H8Br2.

14. Bromine reacts with ethene to form 1,2-dibromoethane.

What is the correct description of the organic intermediate in this reaction? D

A It has a negative charge.

A The R–X bond polarity decreases from RCl to RI.

B The solubility of AgX(s) decreases from AgCl to AgI.

C The ionisation energy of the halogen decreases from Cl to I.

D. The bond energy of R–X decreases from RCl to RI

16. Which term describes the action of NaOH(aq) on a bromoalkane? D

A – CH2– CH2– CCl 2 – CCl 2– CH2– CH2–

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