(a) Interpretation: For the given molecule, the species, a lone pair of electrons or a N-H bond that occupies more space is to be determined. Concept introduction: A monosubstituted cyclohexane is lower in energy (more stable) when the substituent occupies an equatorial position. The equatorial conformer is more stable than the axial conformer because there is more room for the substituent in the equatorial position. The bulkier the substituent on a cyclohexane ring, the more favored is the chair conformation with the substituent in the equatorial position.

Question

Which chair conformation is more stable? Is it the right because bromine has a larger mass than a methyl group? Or is it the left because the methyl group has three hydrogens stemming from the carbon and is therefore ‘bulkier?’

Answer 1

Question

Chapter 4, Problem 4.39P

Interpretation Introduction

(a)

Interpretation:

For the given molecule, the species, a lone pair of electrons or a N-H bond that occupies more space is to be determined.

Concept introduction:

A monosubstituted cyclohexane is lower in energy (more stable) when the substituent occupies an equatorial position. The equatorial conformer is more stable than the axial conformer because there is more room for the substituent in the equatorial position. The bulkier the substituent on a cyclohexane ring, the more favored is the chair conformation with the substituent in the equatorial position.

Interpretation Introduction

(b)

Interpretation:

For the given molecule, the species, a lone pair of electrons or CH3 group that occupies more space is to be determined.

Concept introduction:

A monosubstituted cyclohexane is lower in energy (more stable) when the substituent occupies an equatorial position. The bulkier the substituent on a cyclohexane ring, the more favored is the chair conformation with the substituent in the equatorial position.

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Which chair conformation is more stable? Is it the right because bromine has a larger mass than a methyl group? Or is it the left because the methyl group has three hydrogens stemming from the carbon and is therefore ‘bulkier?’

Draw the alternative chair conformation. Which hydrogens are equatorial? Which are axial? Which are above the plane of the ring? Which are below it?

Ethane spends all its time in the staggered conformation because it has the lowest potential energy. a. True b. False c. Neither

Answer 2

Question

Chapter 4, Problem 4.39P

Interpretation Introduction

(a)

Interpretation:

For the given molecule, the species, a lone pair of electrons or a N-H bond that occupies more space is to be determined.

Concept introduction:

A monosubstituted cyclohexane is lower in energy (more stable) when the substituent occupies an equatorial position. The equatorial conformer is more stable than the axial conformer because there is more room for the substituent in the equatorial position. The bulkier the substituent on a cyclohexane ring, the more favored is the chair conformation with the substituent in the equatorial position.

Interpretation Introduction

(b)

Interpretation:

For the given molecule, the species, a lone pair of electrons or CH3 group that occupies more space is to be determined.

Concept introduction:

A monosubstituted cyclohexane is lower in energy (more stable) when the substituent occupies an equatorial position. The bulkier the substituent on a cyclohexane ring, the more favored is the chair conformation with the substituent in the equatorial position.

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Answer 3

Question

Chapter 4, Problem 4.39P

Interpretation Introduction

(a)

Interpretation:

For the given molecule, the species, a lone pair of electrons or a N-H bond that occupies more space is to be determined.

Concept introduction:

A monosubstituted cyclohexane is lower in energy (more stable) when the substituent occupies an equatorial position. The equatorial conformer is more stable than the axial conformer because there is more room for the substituent in the equatorial position. The bulkier the substituent on a cyclohexane ring, the more favored is the chair conformation with the substituent in the equatorial position.

Interpretation Introduction

(b)

Interpretation:

For the given molecule, the species, a lone pair of electrons or CH3 group that occupies more space is to be determined.

Concept introduction:

A monosubstituted cyclohexane is lower in energy (more stable) when the substituent occupies an equatorial position. The bulkier the substituent on a cyclohexane ring, the more favored is the chair conformation with the substituent in the equatorial position.

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Answer 4

Question

Chapter 4, Problem 4.39P

Interpretation Introduction

(a)

Interpretation:

For the given molecule, the species, a lone pair of electrons or a N-H bond that occupies more space is to be determined.

Concept introduction:

A monosubstituted cyclohexane is lower in energy (more stable) when the substituent occupies an equatorial position. The equatorial conformer is more stable than the axial conformer because there is more room for the substituent in the equatorial position. The bulkier the substituent on a cyclohexane ring, the more favored is the chair conformation with the substituent in the equatorial position.

Interpretation Introduction

(b)

Interpretation:

For the given molecule, the species, a lone pair of electrons or CH3 group that occupies more space is to be determined.

Concept introduction:

A monosubstituted cyclohexane is lower in energy (more stable) when the substituent occupies an equatorial position. The bulkier the substituent on a cyclohexane ring, the more favored is the chair conformation with the substituent in the equatorial position.

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Answer 5

Chapter 4, Problem 4.39P

Interpretation Introduction

(a)

Interpretation:

For the given molecule, the species, a lone pair of electrons or a N-H bond that occupies more space is to be determined.

Concept introduction:

A monosubstituted cyclohexane is lower in energy (more stable) when the substituent occupies an equatorial position. The equatorial conformer is more stable than the axial conformer because there is more room for the substituent in the equatorial position. The bulkier the substituent on a cyclohexane ring, the more favored is the chair conformation with the substituent in the equatorial position.

Interpretation Introduction

(b)

Interpretation:

For the given molecule, the species, a lone pair of electrons or CH3 group that occupies more space is to be determined.

Concept introduction:

A monosubstituted cyclohexane is lower in energy (more stable) when the substituent occupies an equatorial position. The bulkier the substituent on a cyclohexane ring, the more favored is the chair conformation with the substituent in the equatorial position.

Answer 6

Chapter 4, Problem 4.39P

Interpretation Introduction

(a)

Interpretation:

For the given molecule, the species, a lone pair of electrons or a N-H bond that occupies more space is to be determined.

Concept introduction:

A monosubstituted cyclohexane is lower in energy (more stable) when the substituent occupies an equatorial position. The equatorial conformer is more stable than the axial conformer because there is more room for the substituent in the equatorial position. The bulkier the substituent on a cyclohexane ring, the more favored is the chair conformation with the substituent in the equatorial position.

Answer 7

Chapter 4, Problem 4.39P

Interpretation Introduction

(a)

Interpretation:

For the given molecule, the species, a lone pair of electrons or a N-H bond that occupies more space is to be determined.

Concept introduction:

A monosubstituted cyclohexane is lower in energy (more stable) when the substituent occupies an equatorial position. The equatorial conformer is more stable than the axial conformer because there is more room for the substituent in the equatorial position. The bulkier the substituent on a cyclohexane ring, the more favored is the chair conformation with the substituent in the equatorial position.

Answer 8

Interpretation Introduction

(b)

Interpretation:

For the given molecule, the species, a lone pair of electrons or CH3 group that occupies more space is to be determined.

Concept introduction:

A monosubstituted cyclohexane is lower in energy (more stable) when the substituent occupies an equatorial position. The bulkier the substituent on a cyclohexane ring, the more favored is the chair conformation with the substituent in the equatorial position.

Answer 9

Interpretation Introduction

(b)

Interpretation:

For the given molecule, the species, a lone pair of electrons or CH3 group that occupies more space is to be determined.

Concept introduction:

A monosubstituted cyclohexane is lower in energy (more stable) when the substituent occupies an equatorial position. The bulkier the substituent on a cyclohexane ring, the more favored is the chair conformation with the substituent in the equatorial position.

Answer 10

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Answer 11

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Answer 21

Ch. 4 - Prob. 4.1P Ch. 4 - Prob. 4.2P Ch. 4 - Prob. 4.3P Ch. 4 - Prob. 4.4P Ch. 4 - Prob. 4.5P Ch. 4 - Prob. 4.6P Ch. 4 - Prob. 4.7P Ch. 4 - Prob. 4.8P Ch. 4 - Prob. 4.9P Ch. 4 - Prob. 4.10P

Solution Summary: The author explains that a monosubstituted cyclohexane is lower in energy (more stable) when the substituent occupies an equatorial position.

Concept explainers

Chapter 4 Solutions