Why don't tertiary alkyl halides undergo #"S"_N2# reactions?

1 Answer
Bio · Truong-Son N.
Nov 1, 2015

They do not undergo #S_{N}2# reactions due to steric hindrance.

Explanation:

The bulky substituents prevent the nucleophiles from approaching the carbon that is attached directly to the halogen. #S_{N}1# is also more favorable as the neighboring alkyl groups are electron donating, which helps to stabilize the carbocation via a hyperconjugation effect between the central empty #p# orbital and the #"C-H "sigma# bond electrons surrounding it.

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