Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
Question
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Chapter 3.4, Problem 3.5P

(a)

Interpretation Introduction

Interpretation:

From the given Newman projection formulas of tartaric acid, same representations has to be identified.

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, Chapter 3.4, Problem 3.5P

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

(b)

Interpretation Introduction

Interpretation:

From the given Newman projection formulas of tartaric acid, enantiomeric representations has to be identified.

Concept Introduction:

Enantiomers:

Stereoisomers having nonsuperposable mirror image relationship are called as enantiomers.

(c)

Interpretation Introduction

Interpretation:

From the given Newman projection formulas of tartaric acid, meso representation has to be identified.

Concept Introduction:

Meso compound:

It is an achiral compound having two or more chiral centers that also has chiral isomers.

(d)

Interpretation Introduction

Interpretation:

From the given Newman projection formulas of tartaric acid, diastereomers has to be identified.

Concept Introduction:

Diastereomers:

Stereoisomers that are not having nonsuperposable mirror image relationship are called as diastereomers.

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Organic Chemistry

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