CPP-2: HALOALKANES & HALOARENES (CBSE PYQ’s)
1. Write the mechanism of the following reaction : nBuBr +KCN (EtOH+H! O) à nBuCN
2. The treatment of alkyl halide with aqueous KOH leads to the formation of alcohols
but in the presence of alcoholic KOH, alkenes are the major product. Explain.
3. What happens when ?
(i) n-Butyl chloride is treated with alcoholic KOH
(ii) Bromobenzene is treated with Mg in the presence of dry ether
(iii) Chlorobenzene is subjected to hydrolysis
(iv) Ethyl chloride is treated with aqueous KOH
(v) Methyl bromide is treated with sodium in the presence of dry ether
4. Complete the following reaction : CH" − CH = CH! + HBr (1) + aq. KOH(2) →
5. In which of the following molecules the carbon marked with (*) is asymmetric ?
6. Draw the enantiomer of the given molecule below :
7. The major product obtained on reaction of 3-Phenyl propene with HBr in presence of
organic peroxide
(A) 3-Phenyl-1-bromopropane
(B) 1-Phenyl-3-bromopropane
(C) 1-Phenyl-2-bromopropane
(D) 3-Phenyl-2-bromopropane
8. Match the following :
9. To 11. Assertion-Reason type Questions :
(A) Both Assertion & Reason are correct statements, and Reason is the correct
explanation of Assertion.
(B) Both Assertion & Reason are correct statements, and Reason is not the correct
explanation of Assertion.
(C) Assertion is correct but Reason is incorrect.
(D) Assertion is incorrect but Reason is correct.
10. Assertion : Nucleophilic substitution of iodoethane is easier than chloroethane.
Reason : Bond enthalpy of C-I bond is less than that of C-Cl bond.
11. Assertion : Aryl halides undergo nucleophilic substitution reactions with ease.
Reason : The carbon halogen bond in aryl halides has partial double bond character.
12. Assertion : Chlorobenzene is less reactive towards nucleophilic substitution reaction.
Reason : Nitro group in chlorobenzene increases its reactivity towards nucleophilic
substitution reaction.
13. Toluene reacts with halogen in the presence of Iron (III) chloride giving ortho para
halo compounds. The reaction is ______.
(A) Electrophilic elimination reaction
(B) Electrophilic substitution reaction
(C) Free radical addition reaction
(D) Nucleophilic substitution reaction
14. Draw the structure of major monohalo product in each of the following reactions :
15. An alkyl halide (A) of molecular formula C# H$" Cl on treatment with alcoholic KOH
gives two isomeric alkenes (B) and (C) of molecular formula C# H$! . Both alkenes on
hydrogenation give 2, 3-dimethylbutane. Write the structures of (A), (B) and (C).
16. (i) Explain why the dipole moment of Chlorobenzene is lower than that of cyclohexyl
chloride.
(ii) An optically active compounds having molecular formula C% H$& Br reacts with
aqueous KOH to give a racemic mixture of products. Write the mechanism involved
in this reaction.
17. Compound 'A' with molecular formula C' H( Br is treated with aq. KOH solution. The
rate of this reaction depends upon the concentration of the compound 'A' only.
When another optically active isomer 'B' of this compound was treated with aq. KOH
solution, the rate of reaction was found to be dependent on concentration of
compound and KOH both.
(i) Write down the structural formula of both compounds 'A' and 'B'.
(ii) Out of these two compounds, which one will be converted to the product with
inverted configuration?
18. Consider the three types of replacement of group X by group Y as shown here.
This can result in giving compound (A) or (B) or both. What is the process called if
(i) (A) is the only compound obtained?
(ii) (B) is the only compound obtained?
(iii) (A) and (B) are formed in equal proportions?
19. Following compounds are given to you:
2-Bromopentane, 2-Bromo-2-methylbutane, 1-Bromopentane
(i) Write the compound which is most reactive towards S) 2 reaction.
(ii) Write the compound which is optically active.
(iii) Write the compound which is most reactive towards -elimination reaction.
20. Give reasons for the following :
(i) Benzyl chloride is highly reactive towards the S) 1 reaction.
(ii) 2-Bromobutane is optically active but 1-Bromobutane is optically inactive.
(iii) Electrophilic reactions in haloarenes occur slowly.
(iv) p-Dichlorobenzene has higher melting point than those of o- and m- isomers.
(v) Haloarenes are less reactive than haloalkanes towards nucleophilic substitution
reaction.
(vi) The treatment of alkyl chloride with aqueous KOH leads to the formation of
alcohol but in the presence of alcoholic KOH, alkene is the major product. (i) Why are
alkyl halides insoluble in water?
(vii) Why is butan-1-ol optically inactive but butan-2-ol is optically active?
(viii) Although chlorine is an electron withdrawing group, yet it is ortho, para
directing in electrophilic aromatic substitution reactions. Why?
(ix) Racemic mixture is optically inactive.
(x) The presence of nitro group (—NO! ) at o/p positions increases the reactivity of
haloarenes towards nucleophilic substitution reactions.
