NCERT Class XII Chemistry
Chapter - Haloalkanes and Haloarenes
Questions with Solutions
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Question : 29
Total: 31
Which alkyl halide from the following pairs would you expect to react more rapidly by an S N 2 mechanism? Explain your answer.
(i)C H 3 C H 2 C H 2 C H 2 B r or C H 3 C H 2
H C H 3
(ii)C H 3 C H 2
H C H 3 or H 3 C −
− B r
(iii)C H 3
H C H 2 C H 2 B r or C H 3 C H 2
H C H 2 B r
(i)
(ii)
(iii)
Solution:
We know that S N 2 mechanism involves a transition state wherein both, the incoming nucleophile as well as the leaving group are present around the carbon atom. There are 5 atoms simultaneously bonded to it. Thus, for such a transition state to be possible,there should be minimum steric hindrance. Hence, 1° alkyl halides are most reactive towards S N 2 followed by 2° and finally 3°.
1° RX > 2° RX > 3° RX
Based on the above order,
(i)C H 3 C H 2 C H 2 C H 2 B r is more reactive.
(ii)C H 3 C H 2
H C H 3 is more reactive.
(iii)C H 3 −
H − C H 2 − C H 2 − B r is more reactive.
In (iii), it is the proximity of the branched chain— C H 3 that determines the reactivity. In C H 3 C H 2 C H ( C H 3 ) C H 2 the methyl group is closer to the leaving group thereby hindering the transition state.
1° RX > 2° RX > 3° RX
Based on the above order,
(i)
(ii)
(iii)
In (iii), it is the proximity of the branched chain
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