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Q. How many of the following alkyl halides will readily undergo $S_{N} 1$ reaction mechanism?Chemistry Question Image

Haloalkanes and Haloarenes

Solution:

Only benzylic halides $\left(1^{\circ}, 2^{\circ}, 3^{\circ}\right)$, allylic halides $\left(1^{\circ}, 2^{\circ}, 3^{\circ}\right)$ and tertiary alkyl halides undergo $S _{ N } 1$ mechanism most readily.
Benzylic halides: (I), (VI)
Allylic halides: (II), (IV)
Tertiary alkyl halide: (VIII)