Organic Chemistry
Organic Chemistry
3rd Edition
ISBN: 9781119338352
Author: Klein
Publisher: WILEY
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Question
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Chapter 4, Problem 47PP

(a)

Interpretation Introduction

Interpretation:

A bond-line structure for the given compound has to be drawn.

Concept Introduction:

Conformations: Rotation about C-C single bonds allows a compound to adopt a variety of possible three-dimensional shapes.

Newman projections: The new conformations of compounds can be drawn and analyzed by Newman projections. A Newman projection visualizes different conformations of Carbon-carbon chemical bond from front to back with the front carbon represented as a black dot and the back represented as a circle.

The angle between two hydrogens of a Newman projection is called as dihedral angle or torsional angle. This dihedral angle changes as the C-C bond rotates. Two conformations with special attentions are staggered and eclipsed conformation. Staggered conformation is the lowest in energy and the eclipsed conformation is the highest in energy.

For example,

Organic Chemistry, Chapter 4, Problem 47PP , additional homework tip  1

Anti-conformation: The conformation with a dihedral angle of 180 is called anti-conformation.

Organic Chemistry, Chapter 4, Problem 47PP , additional homework tip  2

The two methyl groups achieve maximum separation from each other. In other, methyl groups are closer to each other; their electron clouds are repelling each other, causing an increase in energy. This unfavorable interaction is called gauche interaction.

Drawing Axial and Equatorial substituents:

Organic Chemistry, Chapter 4, Problem 47PP , additional homework tip  3

Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. the other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.

Conversion of chair conformation into Newman projection:

Organic Chemistry, Chapter 4, Problem 47PP , additional homework tip  4

Ring flipping between Newman projections:

Organic Chemistry, Chapter 4, Problem 47PP , additional homework tip  5

Ring flipping is a conformational change that is accomplished only through a rotation of all C-C single bonds. On ring flipping between two chair conformation equatorial changes into axial and vice-versa.

(b)

Interpretation Introduction

Interpretation:

A bond-line structure for the given compound has to be drawn.

Concept Introduction:

Conformations: Rotation about C-C single bonds allows a compound to adopt a variety of possible three-dimensional shapes.

Newman projections: The new conformations of compounds can be drawn and analyzed by Newman projections. A Newman projection visualizes different conformations of Carbon-carbon chemical bond from front to back with the front carbon represented as a black dot and the back represented as a circle.

The angle between two hydrogens of a Newman projection is called as dihedral angle or torsional angle. This dihedral angle changes as the C-C bond rotates. Two conformations with special attentions are staggered and eclipsed conformation. Staggered conformation is the lowest in energy and the eclipsed conformation is the highest in energy.

For example,

Organic Chemistry, Chapter 4, Problem 47PP , additional homework tip  6

Anti-conformation: The conformation with a dihedral angle of 180 is called anti-conformation.

Organic Chemistry, Chapter 4, Problem 47PP , additional homework tip  7

The two methyl groups achieve maximum separation from each other. In other, methyl groups are closer to each other; their electron clouds are repelling each other, causing an increase in energy. This unfavorable interaction is called gauche interaction.

Drawing Axial and Equatorial substituents:

Organic Chemistry, Chapter 4, Problem 47PP , additional homework tip  8

Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. the other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.

Conversion of chair conformation into Newman projection:

Organic Chemistry, Chapter 4, Problem 47PP , additional homework tip  9

Ring flipping between Newman projections:

Organic Chemistry, Chapter 4, Problem 47PP , additional homework tip  10

Ring flipping is a conformational change that is accomplished only through a rotation of all C-C single bonds. On ring flipping between two chair conformation equatorial changes into axial and vice-versa.

(c)

Interpretation Introduction

Interpretation:

A bond-line structure for the given compound has to be drawn.

Concept Introduction:

Conformations: Rotation about C-C single bonds allows a compound to adopt a variety of possible three-dimensional shapes.

Newman projections: The new conformations of compounds can be drawn and analyzed by Newman projections. A Newman projection visualizes different conformations of Carbon-carbon chemical bond from front to back with the front carbon represented as a black dot and the back represented as a circle.

The angle between two hydrogens of a Newman projection is called as dihedral angle or torsional angle. This dihedral angle changes as the C-C bond rotates. Two conformations with special attentions are staggered and eclipsed conformation. Staggered conformation is the lowest in energy and the eclipsed conformation is the highest in energy.

For example,

Organic Chemistry, Chapter 4, Problem 47PP , additional homework tip  11

Anti-conformation: The conformation with a dihedral angle of 180 is called anti-conformation.

Organic Chemistry, Chapter 4, Problem 47PP , additional homework tip  12

The two methyl groups achieve maximum separation from each other. In other, methyl groups are closer to each other; their electron clouds are repelling each other, causing an increase in energy. This unfavorable interaction is called gauche interaction.

Drawing Axial and Equatorial substituents:

Organic Chemistry, Chapter 4, Problem 47PP , additional homework tip  13

Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. the other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.

Conversion of chair conformation into Newman projection:

Organic Chemistry, Chapter 4, Problem 47PP , additional homework tip  14

Ring flipping between Newman projections:

Organic Chemistry, Chapter 4, Problem 47PP , additional homework tip  15

Ring flipping is a conformational change that is accomplished only through a rotation of all C-C single bonds. On ring flipping between two chair conformation equatorial changes into axial and vice-versa.

Blurred answer

Chapter 4 Solutions

Organic Chemistry

Ch. 4.2 - Prob. 4LTSCh. 4.2 - Prob. 8PTSCh. 4.2 - Prob. 9PTSCh. 4.2 - Prob. 10ATSCh. 4.2 - Prob. 5LTSCh. 4.2 - Prob. 11PTSCh. 4.2 - Prob. 12PTSCh. 4.2 - Prob. 13ATSCh. 4.3 - Prob. 6LTSCh. 4.3 - Prob. 14PTSCh. 4.3 - Prob. 15ATSCh. 4.6 - Prob. 7LTSCh. 4.6 - Prob. 16PTSCh. 4.6 - Prob. 17ATSCh. 4.7 - Prob. 18CCCh. 4.8 - Prob. 8LTSCh. 4.8 - Prob. 19PTSCh. 4.8 - Prob. 20ATSCh. 4.11 - Prob. 9LTSCh. 4.11 - Prob. 21PTSCh. 4.11 - Prob. 22ATSCh. 4.11 - Prob. 10LTSCh. 4.11 - Prob. 23PTSCh. 4.11 - Prob. 24ATSCh. 4.12 - Prob. 11LTSCh. 4.12 - Prob. 25PTSCh. 4.12 - Prob. 26ATSCh. 4.12 - Prob. 27CCCh. 4.13 - Prob. 12LTSCh. 4.13 - Prob. 28PTSCh. 4.13 - Prob. 29ATSCh. 4.13 - Prob. 13LTSCh. 4.13 - Prob. 30PTSCh. 4.13 - Prob. 31ATSCh. 4.13 - Prob. 32ATSCh. 4.14 - Prob. 33CCCh. 4.14 - Prob. 34CCCh. 4.14 - Prob. 35CCCh. 4 - Prob. 36PPCh. 4 - Prob. 37PPCh. 4 - Prob. 38PPCh. 4 - Prob. 39PPCh. 4 - Prob. 40PPCh. 4 - Prob. 41PPCh. 4 - Prob. 42PPCh. 4 - Prob. 43PPCh. 4 - Prob. 44PPCh. 4 - Prob. 45PPCh. 4 - Prob. 46PPCh. 4 - Prob. 47PPCh. 4 - Prob. 48PPCh. 4 - Prob. 49PPCh. 4 - Prob. 50PPCh. 4 - Prob. 51PPCh. 4 - Prob. 52PPCh. 4 - Prob. 53PPCh. 4 - Prob. 54PPCh. 4 - Prob. 55PPCh. 4 - Prob. 56PPCh. 4 - Prob. 57PPCh. 4 - Prob. 58PPCh. 4 - Prob. 59PPCh. 4 - Prob. 60PPCh. 4 - Prob. 61IPCh. 4 - Prob. 62IPCh. 4 - Prob. 64IPCh. 4 - Prob. 65IPCh. 4 - Prob. 66IPCh. 4 - Prob. 67IPCh. 4 - Prob. 68IPCh. 4 - Prob. 69IPCh. 4 - Prob. 70IPCh. 4 - All of the following are representations of...Ch. 4 - Prob. 72IPCh. 4 - Which of the following is expected to have the...Ch. 4 - Prob. 74IPCh. 4 - Prob. 75CPCh. 4 - The all-trans-1,2,3,4,5,6-hexaethylcyclohexane...Ch. 4 - Compounds 1 and 2 were prepared, and the...
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