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Haloalkanes and Haloarenes

AIPMT 2010 (Prelims)MCQEasy📈 Topic in 50% papers+4−1
Ques. 1AIPMT 2010 (Prelims)

Which one is most reactive towards SN1 reaction?

  1. C6H5CH(C6H5)Br
  2. C6H5CH(CH3)Br
  3. C6H5C(CH3)(C6H5)Br
  4. C6H5CH2Br

Answer

(3) C6H5C(CH3)(C6H5)Br

Solution

SN1 reactivity depends on the stability of the carbocation formed.

(3) gives C6H5 +C(CH3)(C6H5), a tertiary carbocation stabilised by resonance with two phenyl rings and by hyperconjugation of CH3.

(1) gives a secondary diphenylmethyl cation, (2) a secondary benzylic cation and (4) a primary benzylic cation – all less stable.

(3) is the most reactive towards SN1.

Answer: (3)

Keep practising — Haloalkanes and Haloarenes

Ques. 2AIPMT 2010 (Prelims)

The correct order of increasing reactivity of [figure] C–X bond towards nucleophile in the following compounds is

  1. I < II < IV < III
  2. II < III < I < IV
  3. IV < III < I < II
  4. III < II < I < IV
Ques. 3AIPMT 2009

Which of the following reactions is an example of nucleophilic substitution reaction?

  1. 2RX + 2Na R-R + 2NaX
  2. RX + H2 RH + HX
  3. RX + Mg RMgX
  4. RX + KOH ROH + KX
Ques. 4AIPMT 2009

Trichloroacetaldehyde, CCl3CHO reacts with chlorobenzene in presence of sulphuric acid and produces

  1. [figure]
  2. [figure]
  3. [figure]
  4. [figure]
Ques. 5AIPMT 2008

In an SN2 substitution reaction of the type R-Br + Cl- DMF R-Cl + Br- which one of the following has the highest relative rate?

  1. CH3- CH3 | CH3 |C-CH2Br
  2. CH3CH2Br
  3. CH3CH2CH2Br
  4. CH3- CH3 |CH-CH2Br
Ques. 6AIPMT 2005

Which of the following undergoes nucleophilic substitution exclusively by SN1 mechanism?

  1. Ethyl chloride
  2. Isopropyl chloride
  3. Chlorobenzene
  4. Benzyl chloride
Ques. 7AIPMT 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
Ques. 8AIPMT 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. 9AIPMT 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. 10AIPMT 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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