Student Study Guide and Solutions Manual T/A Organic Chemistry
Student Study Guide and Solutions Manual T/A Organic Chemistry
2nd Edition
ISBN: 9781118647950
Author: David R. Klein
Publisher: WILEY
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Chapter 9.9, Problem 31ATS

(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.

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Student Study Guide and Solutions Manual T/A Organic Chemistry

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