The structures of 3 and 4 with diastereomeric centers have to be drawn Concept Introduction : Sodium cyanoborohydride is a strong reducing agent than sodium borohydride. It reduces the carbonyl group into amine group in a rapid way. So, it is called as reductive amination reactions. Aldehyde or ketone group is reacted with primary amine in the presence of sodium cyanoborohydride as a reducing agent and a proton source in the reaction medium to produce secondary amines . If a carbon is attached with four different groups without any elements of symmetry, then that center has a chirality center. Diastereomers (sometimes called diastereoisomers) are a type of a stereoisomer. Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers. Each stereocenter gives rise to two different configurations and thus increases the number of stereoisomers by a factor of two. To find: Draw the structure of 3 and the reason for its production as a diastereomeric mixture Do reductive amination in compound 2

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Answer 1

Question

Chapter 22, Problem 96CP

(a)

Interpretation Introduction

Interpretation: The structures of 3 and 4 with diastereomeric centers have to be drawn

Concept Introduction:

Sodium cyanoborohydride is a strong reducing agent than sodium borohydride. It reduces the carbonyl group into amine group in a rapid way. So, it is called as reductive amination reactions. Aldehyde or ketone group is reacted with primary amine in the presence of sodium cyanoborohydride as a reducing agent and a proton source in the reaction medium to produce secondary amines.

If a carbon is attached with four different groups without any elements of symmetry, then that center has a chirality center. Diastereomers (sometimes called diastereoisomers) are a type of a stereoisomer. Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers. Each stereocenter gives rise to two different configurations and thus increases the number of stereoisomers by a factor of two.

To find: Draw the structure of 3 and the reason for its production as a diastereomeric mixture

Do reductive amination in compound 2

(b)

Interpretation Introduction

Interpretation: The structures of 3 and 4 with diastereomeric centers have to be drawn

Concept Introduction:

An amide group is formed from an amine compound and the ester group.

If a carbon is attached with four different groups without any elements of symmetry, then that center has a chirality center. Diastereomers (sometimes called diastereoisomers) are a type of a stereoisomer. Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers. Each stereocenter gives rise to two different configurations and thus increases the number of stereoisomers by a factor of two.

To find: Draw the structure of 4 and determine the possibility of its production as a diastereomeric mixture

Decide the nature of the functional groups in compound 3

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Where are the chiral centers in this molecule? Also is this compound meso yes or no?

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Where are the chiral centers in this molecule? Also is this compound meso yes or no?

Answer 2

Question

Chapter 22, Problem 96CP

(a)

Interpretation Introduction

Interpretation: The structures of 3 and 4 with diastereomeric centers have to be drawn

Concept Introduction:

Sodium cyanoborohydride is a strong reducing agent than sodium borohydride. It reduces the carbonyl group into amine group in a rapid way. So, it is called as reductive amination reactions. Aldehyde or ketone group is reacted with primary amine in the presence of sodium cyanoborohydride as a reducing agent and a proton source in the reaction medium to produce secondary amines.

If a carbon is attached with four different groups without any elements of symmetry, then that center has a chirality center. Diastereomers (sometimes called diastereoisomers) are a type of a stereoisomer. Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers. Each stereocenter gives rise to two different configurations and thus increases the number of stereoisomers by a factor of two.

To find: Draw the structure of 3 and the reason for its production as a diastereomeric mixture

Do reductive amination in compound 2

(b)

Interpretation Introduction

Interpretation: The structures of 3 and 4 with diastereomeric centers have to be drawn

Concept Introduction:

An amide group is formed from an amine compound and the ester group.

If a carbon is attached with four different groups without any elements of symmetry, then that center has a chirality center. Diastereomers (sometimes called diastereoisomers) are a type of a stereoisomer. Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers. Each stereocenter gives rise to two different configurations and thus increases the number of stereoisomers by a factor of two.

To find: Draw the structure of 4 and determine the possibility of its production as a diastereomeric mixture

Decide the nature of the functional groups in compound 3

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Answer 3

Question

Chapter 22, Problem 96CP

(a)

Interpretation Introduction

Interpretation: The structures of 3 and 4 with diastereomeric centers have to be drawn

Concept Introduction:

Sodium cyanoborohydride is a strong reducing agent than sodium borohydride. It reduces the carbonyl group into amine group in a rapid way. So, it is called as reductive amination reactions. Aldehyde or ketone group is reacted with primary amine in the presence of sodium cyanoborohydride as a reducing agent and a proton source in the reaction medium to produce secondary amines.

If a carbon is attached with four different groups without any elements of symmetry, then that center has a chirality center. Diastereomers (sometimes called diastereoisomers) are a type of a stereoisomer. Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers. Each stereocenter gives rise to two different configurations and thus increases the number of stereoisomers by a factor of two.

To find: Draw the structure of 3 and the reason for its production as a diastereomeric mixture

Do reductive amination in compound 2

(b)

Interpretation Introduction

Interpretation: The structures of 3 and 4 with diastereomeric centers have to be drawn

Concept Introduction:

An amide group is formed from an amine compound and the ester group.

If a carbon is attached with four different groups without any elements of symmetry, then that center has a chirality center. Diastereomers (sometimes called diastereoisomers) are a type of a stereoisomer. Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers. Each stereocenter gives rise to two different configurations and thus increases the number of stereoisomers by a factor of two.

To find: Draw the structure of 4 and determine the possibility of its production as a diastereomeric mixture

Decide the nature of the functional groups in compound 3

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Answer 4

Question

Chapter 22, Problem 96CP

(a)

Interpretation Introduction

Interpretation: The structures of 3 and 4 with diastereomeric centers have to be drawn

Concept Introduction:

Sodium cyanoborohydride is a strong reducing agent than sodium borohydride. It reduces the carbonyl group into amine group in a rapid way. So, it is called as reductive amination reactions. Aldehyde or ketone group is reacted with primary amine in the presence of sodium cyanoborohydride as a reducing agent and a proton source in the reaction medium to produce secondary amines.

If a carbon is attached with four different groups without any elements of symmetry, then that center has a chirality center. Diastereomers (sometimes called diastereoisomers) are a type of a stereoisomer. Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers. Each stereocenter gives rise to two different configurations and thus increases the number of stereoisomers by a factor of two.

To find: Draw the structure of 3 and the reason for its production as a diastereomeric mixture

Do reductive amination in compound 2

(b)

Interpretation Introduction

Interpretation: The structures of 3 and 4 with diastereomeric centers have to be drawn

Concept Introduction:

An amide group is formed from an amine compound and the ester group.

If a carbon is attached with four different groups without any elements of symmetry, then that center has a chirality center. Diastereomers (sometimes called diastereoisomers) are a type of a stereoisomer. Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers. Each stereocenter gives rise to two different configurations and thus increases the number of stereoisomers by a factor of two.

To find: Draw the structure of 4 and determine the possibility of its production as a diastereomeric mixture

Decide the nature of the functional groups in compound 3

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Answer 5

Chapter 22, Problem 96CP

(a)

Interpretation Introduction

Interpretation: The structures of 3 and 4 with diastereomeric centers have to be drawn

Concept Introduction:

Sodium cyanoborohydride is a strong reducing agent than sodium borohydride. It reduces the carbonyl group into amine group in a rapid way. So, it is called as reductive amination reactions. Aldehyde or ketone group is reacted with primary amine in the presence of sodium cyanoborohydride as a reducing agent and a proton source in the reaction medium to produce secondary amines.

If a carbon is attached with four different groups without any elements of symmetry, then that center has a chirality center. Diastereomers (sometimes called diastereoisomers) are a type of a stereoisomer. Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers. Each stereocenter gives rise to two different configurations and thus increases the number of stereoisomers by a factor of two.

To find: Draw the structure of 3 and the reason for its production as a diastereomeric mixture

Do reductive amination in compound 2

(b)

Interpretation Introduction

Interpretation: The structures of 3 and 4 with diastereomeric centers have to be drawn

Concept Introduction:

An amide group is formed from an amine compound and the ester group.

If a carbon is attached with four different groups without any elements of symmetry, then that center has a chirality center. Diastereomers (sometimes called diastereoisomers) are a type of a stereoisomer. Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers. Each stereocenter gives rise to two different configurations and thus increases the number of stereoisomers by a factor of two.

To find: Draw the structure of 4 and determine the possibility of its production as a diastereomeric mixture

Decide the nature of the functional groups in compound 3

Answer 6

Chapter 22, Problem 96CP

(a)

Interpretation Introduction

Interpretation: The structures of 3 and 4 with diastereomeric centers have to be drawn

Concept Introduction:

Sodium cyanoborohydride is a strong reducing agent than sodium borohydride. It reduces the carbonyl group into amine group in a rapid way. So, it is called as reductive amination reactions. Aldehyde or ketone group is reacted with primary amine in the presence of sodium cyanoborohydride as a reducing agent and a proton source in the reaction medium to produce secondary amines.

If a carbon is attached with four different groups without any elements of symmetry, then that center has a chirality center. Diastereomers (sometimes called diastereoisomers) are a type of a stereoisomer. Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers. Each stereocenter gives rise to two different configurations and thus increases the number of stereoisomers by a factor of two.

To find: Draw the structure of 3 and the reason for its production as a diastereomeric mixture

Do reductive amination in compound 2

Answer 7

Chapter 22, Problem 96CP

(a)

Interpretation Introduction

Interpretation: The structures of 3 and 4 with diastereomeric centers have to be drawn

Concept Introduction:

Sodium cyanoborohydride is a strong reducing agent than sodium borohydride. It reduces the carbonyl group into amine group in a rapid way. So, it is called as reductive amination reactions. Aldehyde or ketone group is reacted with primary amine in the presence of sodium cyanoborohydride as a reducing agent and a proton source in the reaction medium to produce secondary amines.

If a carbon is attached with four different groups without any elements of symmetry, then that center has a chirality center. Diastereomers (sometimes called diastereoisomers) are a type of a stereoisomer. Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers. Each stereocenter gives rise to two different configurations and thus increases the number of stereoisomers by a factor of two.

To find: Draw the structure of 3 and the reason for its production as a diastereomeric mixture

Do reductive amination in compound 2

Answer 8

(b)

Interpretation Introduction

Interpretation: The structures of 3 and 4 with diastereomeric centers have to be drawn

Concept Introduction:

An amide group is formed from an amine compound and the ester group.

If a carbon is attached with four different groups without any elements of symmetry, then that center has a chirality center. Diastereomers (sometimes called diastereoisomers) are a type of a stereoisomer. Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers. Each stereocenter gives rise to two different configurations and thus increases the number of stereoisomers by a factor of two.

To find: Draw the structure of 4 and determine the possibility of its production as a diastereomeric mixture

Decide the nature of the functional groups in compound 3

Answer 9

(b)

Interpretation Introduction

Interpretation: The structures of 3 and 4 with diastereomeric centers have to be drawn

Concept Introduction:

An amide group is formed from an amine compound and the ester group.

If a carbon is attached with four different groups without any elements of symmetry, then that center has a chirality center. Diastereomers (sometimes called diastereoisomers) are a type of a stereoisomer. Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers. Each stereocenter gives rise to two different configurations and thus increases the number of stereoisomers by a factor of two.

To find: Draw the structure of 4 and determine the possibility of its production as a diastereomeric mixture

Decide the nature of the functional groups in compound 3

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 22.2 - Prob. 1LTS Ch. 22.2 - Prob. 1PTS Ch. 22.2 - Prob. 2PTS Ch. 22.2 - Prob. 3ATS Ch. 22.3 - Prob. 4CC Ch. 22.3 - Prob. 5CC Ch. 22.3 - Prob. 6CC Ch. 22.3 - Prob. 7CC Ch. 22.3 - Prob. 8CC Ch. 22.3 - Prob. 9CC

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Chapter 22 Solutions