EBK EXPERIMENTAL ORGANIC CHEMISTRY: A M
EBK EXPERIMENTAL ORGANIC CHEMISTRY: A M
6th Edition
ISBN: 9781305687875
Author: Gilbert
Publisher: CENGAGE LEARNING - CONSIGNMENT
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Chapter 7.6, Problem 2E

(a)

Interpretation Introduction

Interpretation: The number of stereochemically distinct salts formed needs to be determined.

Concept Introduction: The carbon atoms containing 4 different groups attached to it are chiral carbon. Depending on the configuration they can be classified as ( R ) and ( S ). In the R configuration, the arrangement of the priority group is in clockwise direction on the other hand, in the S configuration the arrangement of the priority group is in the anticlockwise direction.

(b)

Interpretation Introduction

Interpretation: The stereochemical relationship between the products formed in the reaction needs to be determined.

Concept Introduction:

The type isomers which are non-superimposable non-mirror image of each other are known as diastereomers. On the other hand, the isomers which are non-superimposable mirror image of each other are known as enantiomers.

(c)

Interpretation Introduction

Interpretation: The pair of salts that can be separated by crystallization needs to be determined. Also, the pairs that are inseparable need to be determined.

Concept Introduction:

The type isomers which are non-superimposable non-mirror image of each other are known as diastereomers. On the other hand, the isomers which are non-superimposable mirror image of each other are known as enantiomers.

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a. Would you expect hemiacetals to be stable in basic solutions? Explain your answer.b. Acetal formation must be catalyzed by an acid. Explain why it cannot be catalyzed by CH3O-.c. Can the rate of hydrate formation be increased by hydroxide ion as well as by acid? Explain.
Why does the melting point (70-71) above match neither the enantiomers’ nor the racemate’s? Does it mean that the substance is impure, or perhaps isn’t even ibuprofen at all? (Racemic mixture:75-77C, Enantiomer:52-53C)
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