why are tertiary alkyl halides practically inert to substitution by SN2 mechanism?

2017-08-04 10:30 pm

回答 (2)

2017-08-04 11:29 pm
In SN2 reaction, the nucleophile attached the back side of the carbon reaction site and halide ion acts as a leaving group simultaneously.

If the reactant is a tertiary halide, the carbon reaction site is attached to 3 bulky alkyl group and a halogen atom. The steric effect of the 3 bulky alkyl groups prevent the nucleophile from attacking the carbon reaction site. Therefore, it is hardly for tertiary halides to undergo SN2 reaction.
2017-08-04 10:39 pm
stearic hindrance - the nucleophile can't get in.


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