Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 2, Problem 53P

(a)

Interpretation Introduction

Interpretation: The energy associated with single H-H eclipsed interaction should be determined.

Concept introduction: Various interconvertible forms that result from rotation around the C–C bind in ethane are termed as conformer. To depict such conformation Newman projections are written. These are obtained by conversion of hashed-wedged line structure simply when molecule is viewed in a plane along the C–C as illustrated below:

  Organic Chemistry: Structure and Function, Chapter 2, Problem 53P , additional homework tip  1

For example, energetics of rotation about the C–C bond for 2,3-dimethylbutane is similar to the potential energy diagram of butane except for the added methyl groups at second and third carbon.

  Organic Chemistry: Structure and Function, Chapter 2, Problem 53P , additional homework tip  2

Because of relatively more bulkiness in the system compared to butane, the energy differences between the anti and all other conformations will increase, with the greatest increase at 180 ° .

(b)

Interpretation Introduction

Interpretation: The energy associated with single CH3-H eclipsed interaction should be determined.

Concept introduction: Various interconvertible forms that result from rotation around the C–C bind in ethane are termed as conformer. To depict such conformation Newman projections are written. These are obtained by conversion of hashed-wedged line structure simply when molecule is viewed in a plane along the C–C as illustrated below:

  Organic Chemistry: Structure and Function, Chapter 2, Problem 53P , additional homework tip  3

For example energetics of rotation about the C–C bond for 2,3-dimethylbutane is similar to the potential energy diagram of butane except for the added methyl groups at second and third carbon.

  Organic Chemistry: Structure and Function, Chapter 2, Problem 53P , additional homework tip  4

(c)

Interpretation Introduction

Interpretation: The energy associated with single methyl-methyl eclipsed interaction should be determined.

Concept introduction: Various interconvertible forms that result from rotation around the C–C bind in ethane are termed as conformer. To depict such conformation Newman projections are written. These are obtained by conversion of hashed-wedged line structure simply when molecule is viewed in a plane along the C–C as illustrated below:

  Organic Chemistry: Structure and Function, Chapter 2, Problem 53P , additional homework tip  5

For example energetics of rotation about the C–C bond for 2,3-dimethylbutane is similar to the potential energy diagram of butane except for the added methyl groups at second and third carbon.

  Organic Chemistry: Structure and Function, Chapter 2, Problem 53P , additional homework tip  6

(d)

Interpretation Introduction

Interpretation: The energy associated with single methyl-methyl gauche interaction should be determined.

Concept introduction: Various interconvertible forms that result from rotation around the C–C bind in ethane are termed as conformer. To depict such conformation Newman projections are written. These are obtained by conversion of hashed-wedged line structure simply when molecule is viewed in a plane along the C–C as illustrated below:

  Organic Chemistry: Structure and Function, Chapter 2, Problem 53P , additional homework tip  7

For example energetics of rotation about the C–C bond for 2,3-dimethylbutane is similar to the potential energy diagram of butane except for the added methyl groups at second and third carbon.

  Organic Chemistry: Structure and Function, Chapter 2, Problem 53P , additional homework tip  8

Because of relatively more bulkiness in the system compared to butane, the energy differences between the anti and all other conformations will increase, with the greatest increase at 180 ° .

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