Chapter 8.10, Problem 25ATS

(a)

Interpretation Introduction

Interpretation:

Product should be predicted for the given reaction conditions.

Concept introduction:

• Anti-dihydroxylation: two hydroxyl groups adding across the double bond from both the planes is known as anti-dihydroxylation.
• This anti-hydroxylation happens when alkene is treated with peroxy acids followed by aqueous acid.
• In this reaction, intermediate is three membered cyclic oxonium ion (epoxide formation), this cyclic strain will be revealed by the attack of nucleophile (water) molecule.
• Instead of water, some other nucleophiles also can attack and give anti-products.

To find: the major product formed for given alkene while treated with peroxy acids followed by aqueous ethanol.

(b)

Interpretation Introduction

Interpretation:

Product should be predicted for the given reaction conditions.

Concept introduction:

• Anti-dihydroxylation: two hydroxyl groups adding across the double bond from both the planes is known as anti-dihydroxylation.
• This anti-hydroxylation happens when alkene is treated with peroxy acids followed by aqueous acid.
• In this reaction, intermediate is three membered cyclic oxonium ion (epoxide formation), this cyclic strain will be revealed by the attack of nucleophile (water) molecule.
• Instead of water, some other nucleophiles also can attack and give anti-products.

To find: the major product formed for given epoxide while treated with phenol.