Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 10, Problem 10.49AP
Interpretation Introduction

(a)

Interpretation:

The mechanism of conversion of enantiomerically pure (R)-CH3CH2CHDOH into (S)-CH3CH2CHD18OH is to be stated.

Concept introduction:

Substitution reaction is one of the types of reaction in which one species is replaced by the other species. Substitution reactions can be done either by SN1 mechanism or by SN2 mechanism. Inversion of the stereochemistry of the product from reactant takes place in SN2 mechanism.

Interpretation Introduction

(b)

Interpretation:

The mechanism of conversion of enantiomerically pure (R)-CH3CH2CHDOH into (R)-CH3CH2CHD18OH is to be stated.

Concept introduction:

Substitution reaction is one of the types of reaction in which one species is replaced by the other species. Substitution reactions can be done either by SN1 mechanism or by SN2 mechanism. Inversion of the stereochemistry of the product from reactant takes place in SN2 mechanism.

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A difficult problem in the synthesis of PGF2α is the introduction of the OH group at C15 in the desired configuration. a. Label this stereogenic center as R or S. b. A well known synthesis of PGF2α involves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship. c. Suggest a reagent to convert A to the single stereoisomer X.
A difficult problem in the synthesis of PGF2α is the introduction of the OH group at C15 in the desired configuration. a. Label this stereogenic center as R or S. b. A well-known synthesis of PGF2α involves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship. d. Suggest a reagent to convert A to the single stereoisomer X.
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