Organic Chemistry, Loose-leaf Version
Organic Chemistry, Loose-leaf Version
8th Edition
ISBN: 9781305865549
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 3.7, Problem 3.10P

(a)

Interpretation Introduction

Interpretation:

The configuration for an enantiomer of naproxen has to be assigned.

Concept Introduction:

Priority rules:

  • Priorities based on atomic number

-H,-CH3,-NH2,-OH,-SH,-Cl,-Br,-IIncreasingpriority

  • When priority cannot be assigned on the basis of the atoms bonded directly to the chiral center

-CH2H,-CH2CH3,-CH2NH2,-CH2OH,-CH2ClIncreasingpriority

  • Atoms participating in a double or triple bond are considered to be bonded to an equivalent number of phantom atoms.

For example,

Organic Chemistry, Loose-leaf Version, Chapter 3.7, Problem 3.10P

  • Priority assignment is made at the first point of difference between groups (should not be based on the larger group).

(b)

Interpretation Introduction

Interpretation:

The percentage of R and S enantiomers in the mixture has to be given.

Concept Introduction:

Enantiomeric excess:

It is the difference betweenthe percentages of twoenantiomers in a given mixture.

Enantiomericexcess(ee)=%R-%S

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Organic Chemistry, Loose-leaf Version

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