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Haloalkanes and Haloarenes

AIPMT 2004MCQEasyNot asked in last 5 yrs+4−1
Ques. 1AIPMT 2004

Which of the following is least reactive in a nucleophilic substitution reaction?

  1. (CH3)3C-Cl
  2. CH2=CHCl
  3. CH3CH2Cl
  4. CH2=CHCH2Cl

Answer

(2) CH2=CHCl

Solution

As per NCERT, in vinyl chloride CH2=CH-Cl the lone pair of Cl is in resonance with the C=C bond:

CH2=CH- Cl: CH2-CH= Cl

⇒ the C–Cl bond acquires partial double-bond character and the carbon is sp2 (bond shorter and stronger).

∴ It is very difficult to replace Cl by a nucleophile, whereas (CH3)3CCl (SN1), CH3CH2Cl (SN2) and allyl chloride (stable allylic carbocation) react readily.

Answer: (2)

Keep practising — Haloalkanes and Haloarenes

Ques. 2AIPMT 2004

Chloropicrin is obtained by the reaction of

  1. steam on carbon tetrachloride
  2. nitric acid on chlorobenzene
  3. chlorine on picric acid
  4. nitric acid on chloroform
Out of syllabus
Ques. 3AIPMT 2002

Reactivity order of halides for dehydrohalogenation is

  1. R-F > R-Cl > R-Br > R-I
  2. R-I > R-Br > R-Cl > R-F
  3. R-I > R-Cl > R-Br > R-F
  4. R-F > R-I > R-Br > R-Cl
Ques. 4AIPMT 2001

An organic compound A (C4H9Cl) on reaction with Na/diethyl ether gives a hydrocarbon which on monochlorination gives only one chloro derivative, then A is

  1. t-butyl chloride
  2. s-butyl chloride
  3. iso-butyl chloride
  4. n-butyl chloride

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