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Question:

In the following pairs of halogen compounds, which compound undergoes faster SN1 reaction?

Answer:

(i)

SN1 reaction proceeds via the formation of carbocation. The alkyl halide (I) is 3° while (II) is 2°. Therefore, (I) forms 3° carbocation while (II) forms 2° carbocation. Greater the stability of the carbocation, faster is the rate of SN1 reaction. Since 3° carbocation is more stable than 2° carbocation. (I), i.e. 2-chloro-2-methylpropane, undergoes faster SN1 reaction than (II) i.e., 3-chloropentane.

 

(ii)

The alkyl halide (I) is 2° while (II) is 1°. 2° carbocation is more stable than 1° carbocation. Therefore, (I), 2-chloroheptane, undergoes faster SN1 reaction than (II), 1-chlorohexane.


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