-->

Haloalkanes And Haloarenes

Question
CBSEENCH12011347

In an SN2  substitution reaction of the type which  straight R minus Br space plus space Cl to the power of minus space rightwards arrow with DMF on top space straight R minus space Cl space plus space Br to the power of minus one of the followings has the highest relative rate?

  • CH3-CH2-CH2Br

  • CH3-CH(CH2)-CH2Br

  • CH3C(CH3)2CH2Br

  • CH3CH2Br

Solution

D.

CH3CH2Br

The relative reactivity of alkyl halide towards SN N reactions is as follows;
Primary > secondary > Tertiary
However, if the primary alkyl halide or the nucleophile/base is sterically hindered the nucleophile will have difficulty to getting the back side of the alpha carbon as a result of this elimination product will be predominant. Here CH3CH2Br is the least hindered, hence it has the highest relative rate towards SN2 reaction.