The mechanism by which reaction proceeds is:

S_{N} 1

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S_{N} 2

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S_{E} 2

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S_{N} i

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Solution

The correct option is D $S_{N} i$
$S_{N} i$ or Nucleophilic substitution with internal return.
Attack of chloride to carbocation from same face resulting in retention of stereochemistry.

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S_{N} 1

S_{N} 2

Consider the reactions

(i) $(C H_{3})_{2} C H - C H_{2} B r C_{2} H_{5} O H - ---- \to (C H_{3})_{2} C H - C H_{2} O C_{2} H_{5} + H B r$

(ii) $(C H_{3})_{2} C H - C H_{2} B r C_{2} H_{S} O^{-} - ---- \to (C H_{3})_{2} C H C H_{2} O C_{2} H_{5} + B r^{-}$

The mechanism of reactions (i) & (ii) are respectively

Formation of two isomeric cyanides in the following reaction. $C H_{3} C H = C H C H_{2} C l + K C N (a l c .)$ is due to

S_{N} 2

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