Question

Compared to methoxide which nucleophile is worse for an sn2 reaction

Answer 1

In an SN2 reaction when a methoxide ion (CH 3 O –) approaches a tetravalent carbon atom, it readily reacts. However, if tertiary butoxide ion C (CH 3) 3 O – is allowed to react with the same tetravalent carbon atom, it will face severe steric hindrance. Thus, the ability of tertiary butoxide ion to function as a nucleophile is sufficiently low.

Answer 2

Methoxide is a stronger nucleophile than most other alkoxide nucleophiles, due to the electron-donating nature of the methyl group. Therefore, in an SN2 reaction, other alkoxide nucleophiles would generally be considered weaker and less reactive than methoxide. However, there are many factors that can influence the reactivity of a nucleophile beyond simple electron-donating effects, so the answer to this question would ultimately depend on the specific reaction conditions and other experimental details.