(a) Interpretation: A boat conformation for the given compound is to be drawn. Concept introduction: The conformation of cyclohexane is a type of 3 − D shape of cyclohexane molecule. There are total four types of significant conformations of cyclohexane exists which are chair conformation, half-chair conformation, boat conformation and twist-boat conformation. The switching of cyclohexane molecule is very easy between the four conformations.

Question

1. What happens to the axial bonds when a chair conformation is converted to another chair conformation? The overall process of converting one chair conformation to another chair conformation is known as RING INVERSION or ring flipping and is a very rapid process. The cyclohexane ring inverts approximately 10 time a second at room temperature. 2. Show this interconversion by drawing the two chair conformations and putting a reversible arrow between them to indicate a dynamic equilibrium. 3. If we have a methylcyclohexane molecule and this undergoes ring inversion, whatwill be the resulting structure? ?

Answer 1

Question

Chapter 7, Problem 7.6P

Interpretation Introduction

(a)

Interpretation:

A boat conformation for the given compound is to be drawn.

Concept introduction:

The conformation of cyclohexane is a type of 3−D shape of cyclohexane molecule. There are total four types of significant conformations of cyclohexane exists which are chair conformation, half-chair conformation, boat conformation and twist-boat conformation. The switching of cyclohexane molecule is very easy between the four conformations.

Interpretation Introduction

(b)

Interpretation:

A boat conformation for the given compound is to be drawn.

Concept introduction:

The conformation of cyclohexane is a type of 3−D shape of cyclohexane molecule. There are total four types of significant conformations of cyclohexane exists which are chair conformation, half-chair conformation, boat conformation and twist-boat conformation. The switching of cyclohexane molecule is very easy between the four conformations.

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1. What happens to the axial bonds when a chair conformation is converted to another chair conformation? The overall process of converting one chair conformation to another chair conformation is known as RING INVERSION or ring flipping and is a very rapid process. The cyclohexane ring inverts approximately 10 time a second at room temperature. 2. Show this interconversion by drawing the two chair conformations and putting a reversible arrow between them to indicate a dynamic equilibrium. 3. If we have a methylcyclohexane molecule and this undergoes ring inversion, whatwill be the resulting structure? ?

There are three diastereomers of 2-bromo-1,3-dimethylcyclohexane. (a) Using the orientation of the chair conformation shown below, draw all three diastereomers of 2-bromo-1,3-dimethyleyclohexane. Follow the numbering given when placing the positions of the two methyl groups and make sure that the bromine leaving group remains in the axial position as shown. 1 2 3 Br Diastereomer 1 Diastereomer 2 Diastereomer 3 (b) Only 2 of these diastereomers undergo an E2 reaction with HO-. Based on the nature of the required transition states for E2 reactions, indicate with an asterisks *, which of the ones you drew in part (a) above undergoes an E2 reaction? (c) The diastereomer that does not undergo an E2 reaction, reacts with HO to form the SN2 product instead. Draw the structure of this SN2 product.

a) Draw the two chair conformations for the compound below, indicating which is more stable. OH CHO b) This molecule is a compound with an intense flowery odor used in perfumes, but it isomerizes rapidly in base to its odorless diastereoisomer. Draw the chair conformation of this diastereoisomer and explain why the isomerization occurs readily.