Draw the major product formed in the following reaction of an epoxide with methoxide in methanol

Chemistry Jan 01, 2021

Draw the major product formed in the following reaction of an epoxide with methoxide in methanol.
H3C
H3C
/0

CH3OH
Draw the major product formed in the following reaction of an epoxide with acidic methanol.
0
H3C
\,..77 CH3
H3C
CH3OH
H2504

Expert Solution

1.Explanation | Common mistakes | Hint for next step

Methoxide ion is a strong nucleophile and it attacks in less substituted site. The opening of epoxide ring takes place and abstracts proton to form an alcohol product.

2.Explanation | Common mistakes

In this reaction, the lone pair electrons of oxygen in the epoxide undergo protonation by an acid. As methanol is less nucleophilic, it attacks the epoxide in a more substituted site and opens the epoxide ring by stabilizing the cation. Then, the cation in oxygen is stabilized by the cleavage of a hydride ion.

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