Why do tertiary halides react faster in SN1 mechanism but are slow to reactivity in an SN2 mechanism?

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Why do tertiary halides react faster in SN1 mechanism but are slow to reactivity in an SN2 mechanism?

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Answer 1 · 2016-10-11T17:10:46

Well, $S_{N} 2$ $S_N2$ processes are essentially bond-making reactions,......

Explanation:

.......whereas $S_{N} 1$ $S_N1$ processes are essentially bond-breaking reactions., and of course, are only dependent on the concentration of the electrophile.

A bond making process at a tertiary carbon centre, for instance, is unlikely to be kinetically favoured, given the shrubbery around the $3^{\circ}$ $3^@$ carbon.

On the other hand, this same shrubbery is likely to favour bond-breaking kinetically, and tend to stabilize a $3^{\circ}$ $3^@$ carbocation, which is conceived to be an intermediate in an $S_{N} 1$ $S_N1$ process :

$R_{1} R_{2} R_{3} C - X \to R_{1} R_{2} R_{3} C^{+} + X^{-}$ $R_1R_2R_3C-X rarr R_1R_2R_3C^(+) +X^-$

Hydrocarbyl substitution at carbon thus stabilizes the carbocation kinetically and thermodynamically, and favour unimolecular nucleophilic substitution.

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Why do tertiary halides react faster in SN1 mechanism but are slow to reactivity in an SN2 mechanism?

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