Question

Complete the mechanism for the base-catalyzed opening of the epoxide below by adding any missing atoms, bonds, charges, nonbonding electron pairs, and curved arrows.

Answer 1

concepts and reason

Epoxide is a three membered ring made up of two carbon atoms and one oxygen atom. Epoxides are cyclic ethers. Due to its ring size, it is highly strained and very reactive. Epoxide ring opening takes place with respect to addition of acid and base.

Fundamentals

Ring opening of epoxide with acid:

In the presence of base, the nucleophile attacks the epoxide ring at more substituted site and inverse stereochemistry takes place.

Ring opening of epoxide with base:

The backside attack of nucleophile takes place in less substituted site and then it undergoes protonation to form a product.

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