VELAMMAL BHODI- KUMBAKONAM

CLASS :12 CHEMISTRY cbse board wrap up

UNIT:1 Haloalkanes & Haloarenes

One mark:
1.Which of the following reactions is a halogenated exchange reaction :

2.The synthesis of alkyl fluoride is best obtained from :

(a) Free radicals (b) Swartz reaction
(c) Sandmeyer reaction (d) Finkelstein reaction
3. In the reaction R OH + HCl ZnCl2 RCl + H2O, what is the correct order of
reactivity of alcohol ?
(a) 1 < 2 < 3 (b) 1 > 3 > 2 (c) 1 > 2 > 3 (d) 3 > 1 > 2
4.The species that attacks benzene in following is :

5.The conversion of an alkyl halide into an alkene by alcoholic KOH is classified as

(a) a substitution reaction (b) an addition reaction
(c) a dehydrohalogenation reaction (d) a dehydration reaction
6.Racemisation occurs in
(a) SN 1 reaction (b) SN 2 reaction
(c) Neither SN 1 nor SN 2 reaction (d) SN 2 reaction as well as SN 1 reaction
7.Which of the following belongs to the class of Vinyl halides ?

8.Retention of configuration is observed in

(a) SN 1 reaction (b) SN 2 reaction
(c) Neither SN 1 nor SN 2 reaction (d) SN 2 reaction as well as SN 1 reaction
9.Auto oxidation of chloroform in air and sunlight produces a poisonous gas
known as
(a) Tear gas (b) Mustard gas
(c) Phosgene gas (d) Chlorine gas
10.Inversion of configuration occurs in
(a) SN 2 reaction (b) SN 1 reaction
(c) Neither SN 2 nor SN 1 reaction (d) SN 1 as well as SN 2 reaction
11.Which of the following is not true about enantiomers ?
(a) They have the same density. (b) They have the same melting or boiling point.
(c) They have the same specific rotation. (d) They have the same chemical reactivity.
12.Which of the following has the highest melting point ?
(a) o-Dichlorobenzene (b) m-Dichlorobenzene
(c) p-Dichlorobenzene (d) All have the same melting point
13.Which of the following belongs to the class of alkyl halides ?

14. Reaction of 1-phenyl-2-chloropropane with alcoholic KOH gives mainly :

(a) 1-phenylpropene (b) 3-phenylpropene
(c) 1-phenylpropan-3-ol (d) 1-phenylypropan-2-ol
15.Which of the following molecules has a chiral centre correctly labelled with an asterisk (*)
?
(a) CH3C*HBrCH3 (b) CH3C*HClCH2Br
(c) HOCH2C*H(OH)CH2OH (d) CH3C*Br2CH3
15.A primary alkyl halide would prefer to undergo ___________.
(A) SN2 reaction (B) SN1 reaction
(C) Electrophilic substitution reaction (D) Racemisation
16.The compound which undergoes SN1 reaction most rapidly is :
17. Which of the following alkyl halides will undergo SN1 reaction most readily ?
A) (CH3)3 - I (b)(CH3)3 - Br (C) (CH3 )3- Cl (D) (CH3 )3- F
18.Which of the following is most reactive towards nucleophilic substitution reaction ?

19.

20.Which of the following is a benzylic halide ?

21. Butanenitrile may be prepared by heating :

(A) propyl chloride with KCN (B) butyl chloride with KCN
(C) propyl alcohol with KCN (D) butyl alcohol with KCN
22.
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24.

25.

26.
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Assertion and reason

1.Assertion (A) : Nucleophilic substitution reaction of an optically active halide gives a
mixture of enantiomers.
Reason (R) : SN 2 reactions of optically active halides are accompanied by inversion of
configuration.
2.Assertion (A) : . Nucleophilic substitution of iodoethane is easier than chloroethane
Reason (R) : Bond enthalpy of C-I bond is less than that of C-Cl bond.
3.Assertion (A) : Elevation in boiling point is a colligative property.
Reason (R) : in boiling point. The lowering of vapour pressure of solution causes elevation
4.Assertion (A) : reaction. Chlorobenzene is resistant to electrophilic substitution 1
Reason (R) :C-Cl bond in chlorobenzene acquires partial double bond characters due to
resonance.
5.Assertion (A) : Chlorobenzene is resistant to nucleophilic substitution reaction at room
temperature.
Reason (R) : C–Cl bond gets weaker due to resonance.
6.

7.

Two marks
1. (i) Write the structure of 1-chloro-4-ethylcyclohexane.
(ii) Why is sulphuric acid not used during the reactions of alcohols with KI ?
2. (i) Arrange the following in increasing order of their boiling points :
1-chloropropane, 2-chloropropane, 1-chlorobutane
(ii) What is an ambident nucleophile ? Give one example.
3.What happens when :
(a) Isopropyl chloride is treated with Na in dry ether ?
(b) Ethyl chloride is treated with AgCN ?
4.What happens when :
(a) 1-chlorobutane is treated with alcoholic KOH ?
(b) Chlorobenzene is treated with sodium in dry ether ?
5.

6. An alkyl halide (A) of molecular formula C6H13Cl on treatment with alcoholic KOH
gives two isomeric alkenes (B) and (C) of molecular formula C6H12. Both alkenes on
hydrogenation give 2,3-dimethylbutane. Write the structures of (A), (B) and (C).
7. Why is boiling point of o-dichlorobenzene higher than p-dichlorobenzene but melting
point of para isomer is higher than ortho isomer ?
8.Write equations for the following :
(a) Oxidation of chloroform by air and light
(b) Reaction of chlorobenzene with CH3Cl / anhyd. AlCl3
9.Why haloarenes are not reactive towards nucleophilic substitution reaction ? Give two
reasons.
10.(a) Out of (CH3)3C Br and (CH3)3C I, which one is more reactive towards SN1 and why ?
(b) Write the product formed when p-nitrochlorobenzene is heated with aqueous NaOH at
443 K followed by acidification.
11.(a) Draw the structures of major monohalo products in each of the following reactions :
12.Give reasons for the following :
i) Grignard reagent should be prepared under anhydrous conditions.
(ii) Alkyl halides give alcohol with aqueous KOH whereas in the presence of alcoholic KOH,
alkenes are formed.
13.(a) In the following pair of compounds, which compound undergoes SN2 reaction faster
and why ?

14.

15(a) Which one of the following pairs of substances undergoes SN1 reaction faster and why
?
CH3- CH2- CH2- Cl OR CH2 = CH- CH2-Cl
(b) Write the major product in the following :

15. a)Which halogen compound in the following pair will react faster in SN2 reactions and
why ?
CH3- CH2- I OR CH3- CH2- Br
(b) Why is chloroform stored in closed dark coloured bottles ?
17.(a) Which halogen compound in the following pair will react faster in SN1 reaction and
why ?

16. a) Why is the dipole moment of chlorobenzene lower than that of cyclohexyl chloride ?
(b) Which halogen compound in the following pair will react faster in SN2 reaction and why
?
(c) Why does the presence of nitro groups at ortho- and para- positions in haloarenes increase
their reactivity towards nucleophilic substitution reaction ?
18.

19.

20.
3marks
1.(i) Why do tertiary alkyl halides undergo SN1 reaction at a faster rate ?
(ii) Define Enantiomers.
(iii) Why is chloroform stored in dark coloured air tight bottles ?
2.(i) Write the major alkene that would be formed by dehydrohalogenation of 2-
Bromopentane.
(ii) Which would undergo SN2 reaction at a faster rate and
why ?

(iii) Why is chlorobenzene less reactive towards nucleophilic substitution reaction ?

3.(a) Out of Chlorcyclohexane and CH2 Cl, which one is more reactive towards SN 2
reaction and why ?
(b) Out of chlorobenzene and p-nitrochlorobenzene which is more reactive towards
nucleophilic substitution reaction and why ?
(c) Out of 2-Bromopentane and 1-Bromopentane which one is optically active and why ?
(d) Define ambident nucleophile with an example.
4.(a) p-nitrochlorobenzene undergoes nucleophilic substitution reaction faster than
chlorobenzene.
(b) Why is ( )-Butan-2-ol optically inactive, though it contains a chiral carbon atom ?
(c) Why is chloroform kept in airtight dark coloured bottle ?
(d) Write the major product formed when 2-Bromobutane is heated with alcoholic KOH.
5.Write main product formed when :
(a) Methyl chloride is treated with NaI/Acetone.
(b) 2,4,6-trinitrochlorobenzene is subjected to hydrolysis.
(c) n-Butyl chloride is treated with alcoholic KOH.
6.Write main product formed when :
(a) Methyl chloride is treated with KCN.
(c) Methyl chloride is treated with sodium in the presence of dry ether.
7.
8.Answer any 3 of the following :
(a) Which isomer of C5H10 gives a single monochloro compound C5H9Cl
in bright sunlight ?
(b) Arrange the following compounds in increasing order of reactivity
towards SN 2 reaction :
2-Bromopentane, 1-Bromopentane, 2-Bromo-2-methylbutane
(c) Why p-dichlorobenzene has higher melting point than those of ortho
and meta-isomers ?
(d) Identify A and B in the following :

9.Account for the following :

(a) Benzyl chloride is highly reactive towards SN1 reaction.
10.

(b) Out of chlorobenzene and 2,4,6-trinitrochlorobenzene, which is more reactive towards

nucleophilic substitution and why ?
(c) Which isomer of C4H9Cl has the lowest boiling point ?
11. Give reasons for the following :
(a) Chlorine is ortho/para directing in electrophilic aromatic substitution reactions, though
chlorine is an electron withdrawing group.
b) Racemic mixture is optically inactive.
(c) Allyl chloride is hydrolysed more readily than n-propyl chloride.
15.(a) What type of nucleophilic substitution (SN1 or SN2) occurs in the hydrolysis of 2-
Bromobutane to form (±)-Butan-2-ol ? Give reason. (b) What happens when chlorobenzene
and methyl chloride are treated with sodium metal in dry ether ?
16.
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