Chair conformations and the position of substituents need to be identified for the given set of compounds. Concept introduction: Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90 ° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below. When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position. To draw and explain : chair conformation and identify the substituent position.

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Answer 1

Question

Chapter 26.6, Problem 22CC

(a)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

(b)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

(c)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

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1. Using Online resources and chemical structures hand draw four different organic compounds (not those already shown in your handout) that are chiral, optically active (a pair of enantiomers will count as one). Pay attention to correct stereochemistry 2. Write or type a short paragraph to Discuss the stereochemical relationship between the four compounds.

Answer 2

Question

Chapter 26.6, Problem 22CC

(a)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

(b)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

(c)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

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Answer 3

Question

Chapter 26.6, Problem 22CC

(a)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

(b)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

(c)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

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Answer 4

Question

Chapter 26.6, Problem 22CC

(a)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

(b)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

(c)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

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Answer 5

Chapter 26.6, Problem 22CC

(a)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

(b)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

(c)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

Answer 6

Chapter 26.6, Problem 22CC

(a)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

Answer 7

Chapter 26.6, Problem 22CC

(a)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

Answer 8

(b)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

Answer 9

(b)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

Answer 10

(c)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

Answer 11

(c)

Interpretation Introduction

Interpretation:

Chair conformations and the position of substituents need to be identified for the given set of compounds.

Concept introduction:

Ring-flipping is a phenomenon known as ring inversion that involves rotation about the single bonds of cyclic conformers. Usually this happens in cyclohexane ring. When ring flip happens in the cyclohexane, the axially and equatorially substituted groups are inverted. The ring-flipping also happens in a fused ring system. Decalin is a fused ring system. There are two stereoisomers for decalin, namely cis-decalin and trans-decalin. If the substituent is facing away from the ring or which makes 90° with the ring plane means it is in axial position and the substituent which makes a small angle with the ring plane is said to be in equatorial position. The chair-conformation of cyclohexane is the most stable one as there is a less strain on the ring and no steric hindrance. The cyclohexane fused system can be drawn in chair conformation as given below.

When viewing the molecule from the top the bonds which are said to be in parallel with the viewing angle are in axial position and which are not parallel are known to be in equatorial position.

To draw and explain: chair conformation and identify the substituent position.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 26.2 - Prob. 1CC Ch. 26.2 - Prob. 2CC Ch. 26.3 - Prob. 1LTS Ch. 26.3 - Prob. 3PTS Ch. 26.4 - Prob. 7CC Ch. 26.4 - Prob. 8CC Ch. 26.4 - Prob. 2LTS Ch. 26.4 - Prob. 9PTS Ch. 26.4 - Prob. 3LTS Ch. 26.4 - Prob. 12PTS

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Chapter 26 Solutions