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

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asked Dec 26, 2017 in Chemistry by sforrest072 (157,439 points) 61 410 949

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

1 Answer

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answered Dec 26, 2017 by mdsamim (213,225 points) 5 10 15
selected Dec 26, 2017 by sforrest072
 
Best answer

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), 1chlorohexane.

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