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Reactions of Alkyl Halides

Which would u...

Question

Which would undergo $S_{N} 1$ reaction faster in the following pair and why?
$C H_{3} - C H_{2} - B r and C H_{3} - C H_{3} | C | B r - C H_{3}$

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Solution

Reactivity in $S_{N} 1$ reaction depends upon the stability of carbocation intermediate formed after ionization of alkyl halide. Since $H_{3} C - C H_{3} | C | B r - C H_{3}$ will give more stable $3^{\circ}$ carbocation $⎛ ⎜ ⎜ ⎝ C H_{3} - C H_{3} | C + - C H_{3} ⎞ ⎟ ⎟ ⎠$ , therefore, it is more reactive than $C H_{3} C H_{2} - B r$ which upon ionization gives $1^{\circ}$ carbocation $(C H_{3} - {+ C H}_{2})$ of lesser stability.

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