The reagent and condition is to be proposed for step 1. Concept introduction: Friedal – Crafts alkylation (or acylation): Friedal – Crafts alkylation (or acylation) is one of the electrophilic substitution reaction. Alkyl halide or acyl halides reaction with benzene (or electron donating group present in the benzene ring) in the presence of anhydrous aluminum trichloride which gives the corresponding alkylated or acylated compound.

Question

In an aqueous solution containing sodium bicarbonate, aniline reacts quickly withbromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions,however, and the yields (mostly m-nitroaniline) are poor.(a) What conditions are used for nitration, and what form of aniline is present under theseconditions?

Answer 1

Question

Chapter 23, Problem 23.64P

(a)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 1.

Concept introduction:

Friedal – Crafts alkylation (or acylation):

Friedal – Crafts alkylation (or acylation) is one of the electrophilic substitution reaction. Alkyl halide or acyl halides reaction with benzene (or electron donating group present in the benzene ring) in the presence of anhydrous aluminum trichloride which gives the corresponding alkylated or acylated compound.

(b)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 2 and step 3.

Concept introduction:

Oxime formation: Aldehyde or ketone is reaction with hydroxylamine and sodium methoxide which yields oxime

(c)

Interpretation Introduction

Interpretation:

The reductive amination is to be explained and the explanation has to be given for two step synthesis of amination is used rather than reductive amination.

Concept introduction:

Reductive amination reaction: Amination is the process by which an amine group is introduced into an organic molecule.

The conversion of Carbonyl group in to amine via imine intermediate is called reductive amination.

(D)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 4 and step 5.

Concept introduction:

Reduction: Aldehydes or ketones undergoing reduction by using reducing agent like LAH or NaBH₄ which provides alcohol.

(E)

Interpretation Introduction

Interpretation:

The possible stereoisomer’s has to be shown if the product is chiral.

Concept introduction:

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

Achiral:

A molecule is superimposable on its mirror image is called achiral molecule.

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In an aqueous solution containing sodium bicarbonate, aniline reacts quickly withbromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions,however, and the yields (mostly m-nitroaniline) are poor.(a) What conditions are used for nitration, and what form of aniline is present under theseconditions?

Triethanolamine, (HOCH2CH2)3N, is a widely used biological buffer, with maximum buffering capacity at pH 7.8. Propose a synthesis of this compound from ethylene oxide and ammonia.

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Answer 2

Question

Chapter 23, Problem 23.64P

(a)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 1.

Concept introduction:

Friedal – Crafts alkylation (or acylation):

Friedal – Crafts alkylation (or acylation) is one of the electrophilic substitution reaction. Alkyl halide or acyl halides reaction with benzene (or electron donating group present in the benzene ring) in the presence of anhydrous aluminum trichloride which gives the corresponding alkylated or acylated compound.

(b)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 2 and step 3.

Concept introduction:

Oxime formation: Aldehyde or ketone is reaction with hydroxylamine and sodium methoxide which yields oxime

(c)

Interpretation Introduction

Interpretation:

The reductive amination is to be explained and the explanation has to be given for two step synthesis of amination is used rather than reductive amination.

Concept introduction:

Reductive amination reaction: Amination is the process by which an amine group is introduced into an organic molecule.

The conversion of Carbonyl group in to amine via imine intermediate is called reductive amination.

(D)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 4 and step 5.

Concept introduction:

Reduction: Aldehydes or ketones undergoing reduction by using reducing agent like LAH or NaBH₄ which provides alcohol.

(E)

Interpretation Introduction

Interpretation:

The possible stereoisomer’s has to be shown if the product is chiral.

Concept introduction:

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

Achiral:

A molecule is superimposable on its mirror image is called achiral molecule.

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Answer 3

Question

Chapter 23, Problem 23.64P

(a)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 1.

Concept introduction:

Friedal – Crafts alkylation (or acylation):

Friedal – Crafts alkylation (or acylation) is one of the electrophilic substitution reaction. Alkyl halide or acyl halides reaction with benzene (or electron donating group present in the benzene ring) in the presence of anhydrous aluminum trichloride which gives the corresponding alkylated or acylated compound.

(b)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 2 and step 3.

Concept introduction:

Oxime formation: Aldehyde or ketone is reaction with hydroxylamine and sodium methoxide which yields oxime

(c)

Interpretation Introduction

Interpretation:

The reductive amination is to be explained and the explanation has to be given for two step synthesis of amination is used rather than reductive amination.

Concept introduction:

Reductive amination reaction: Amination is the process by which an amine group is introduced into an organic molecule.

The conversion of Carbonyl group in to amine via imine intermediate is called reductive amination.

(D)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 4 and step 5.

Concept introduction:

Reduction: Aldehydes or ketones undergoing reduction by using reducing agent like LAH or NaBH₄ which provides alcohol.

(E)

Interpretation Introduction

Interpretation:

The possible stereoisomer’s has to be shown if the product is chiral.

Concept introduction:

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

Achiral:

A molecule is superimposable on its mirror image is called achiral molecule.

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Answer 4

Question

Chapter 23, Problem 23.64P

(a)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 1.

Concept introduction:

Friedal – Crafts alkylation (or acylation):

Friedal – Crafts alkylation (or acylation) is one of the electrophilic substitution reaction. Alkyl halide or acyl halides reaction with benzene (or electron donating group present in the benzene ring) in the presence of anhydrous aluminum trichloride which gives the corresponding alkylated or acylated compound.

(b)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 2 and step 3.

Concept introduction:

Oxime formation: Aldehyde or ketone is reaction with hydroxylamine and sodium methoxide which yields oxime

(c)

Interpretation Introduction

Interpretation:

The reductive amination is to be explained and the explanation has to be given for two step synthesis of amination is used rather than reductive amination.

Concept introduction:

Reductive amination reaction: Amination is the process by which an amine group is introduced into an organic molecule.

The conversion of Carbonyl group in to amine via imine intermediate is called reductive amination.

(D)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 4 and step 5.

Concept introduction:

Reduction: Aldehydes or ketones undergoing reduction by using reducing agent like LAH or NaBH₄ which provides alcohol.

(E)

Interpretation Introduction

Interpretation:

The possible stereoisomer’s has to be shown if the product is chiral.

Concept introduction:

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

Achiral:

A molecule is superimposable on its mirror image is called achiral molecule.

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Answer 5

Chapter 23, Problem 23.64P

(a)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 1.

Concept introduction:

Friedal – Crafts alkylation (or acylation):

Friedal – Crafts alkylation (or acylation) is one of the electrophilic substitution reaction. Alkyl halide or acyl halides reaction with benzene (or electron donating group present in the benzene ring) in the presence of anhydrous aluminum trichloride which gives the corresponding alkylated or acylated compound.

(b)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 2 and step 3.

Concept introduction:

Oxime formation: Aldehyde or ketone is reaction with hydroxylamine and sodium methoxide which yields oxime

(c)

Interpretation Introduction

Interpretation:

The reductive amination is to be explained and the explanation has to be given for two step synthesis of amination is used rather than reductive amination.

Concept introduction:

Reductive amination reaction: Amination is the process by which an amine group is introduced into an organic molecule.

The conversion of Carbonyl group in to amine via imine intermediate is called reductive amination.

(D)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 4 and step 5.

Concept introduction:

Reduction: Aldehydes or ketones undergoing reduction by using reducing agent like LAH or NaBH₄ which provides alcohol.

(E)

Interpretation Introduction

Interpretation:

The possible stereoisomer’s has to be shown if the product is chiral.

Concept introduction:

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

Achiral:

A molecule is superimposable on its mirror image is called achiral molecule.

Answer 6

Chapter 23, Problem 23.64P

(a)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 1.

Concept introduction:

Friedal – Crafts alkylation (or acylation):

Friedal – Crafts alkylation (or acylation) is one of the electrophilic substitution reaction. Alkyl halide or acyl halides reaction with benzene (or electron donating group present in the benzene ring) in the presence of anhydrous aluminum trichloride which gives the corresponding alkylated or acylated compound.

Answer 7

Chapter 23, Problem 23.64P

(a)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 1.

Concept introduction:

Friedal – Crafts alkylation (or acylation):

Friedal – Crafts alkylation (or acylation) is one of the electrophilic substitution reaction. Alkyl halide or acyl halides reaction with benzene (or electron donating group present in the benzene ring) in the presence of anhydrous aluminum trichloride which gives the corresponding alkylated or acylated compound.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 2 and step 3.

Concept introduction:

Oxime formation: Aldehyde or ketone is reaction with hydroxylamine and sodium methoxide which yields oxime

Answer 9

(b)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 2 and step 3.

Concept introduction:

Oxime formation: Aldehyde or ketone is reaction with hydroxylamine and sodium methoxide which yields oxime

Answer 10

(c)

Interpretation Introduction

Interpretation:

The reductive amination is to be explained and the explanation has to be given for two step synthesis of amination is used rather than reductive amination.

Concept introduction:

Reductive amination reaction: Amination is the process by which an amine group is introduced into an organic molecule.

The conversion of Carbonyl group in to amine via imine intermediate is called reductive amination.

Answer 11

(c)

Interpretation Introduction

Interpretation:

The reductive amination is to be explained and the explanation has to be given for two step synthesis of amination is used rather than reductive amination.

Concept introduction:

Reductive amination reaction: Amination is the process by which an amine group is introduced into an organic molecule.

The conversion of Carbonyl group in to amine via imine intermediate is called reductive amination.

Answer 12

(D)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 4 and step 5.

Concept introduction:

Reduction: Aldehydes or ketones undergoing reduction by using reducing agent like LAH or NaBH₄ which provides alcohol.

Answer 13

(D)

Interpretation Introduction

Interpretation:

The reagent and condition is to be proposed for step 4 and step 5.

Concept introduction:

Reduction: Aldehydes or ketones undergoing reduction by using reducing agent like LAH or NaBH₄ which provides alcohol.

Answer 14

(E)

Interpretation Introduction

Interpretation:

The possible stereoisomer’s has to be shown if the product is chiral.

Concept introduction:

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

Achiral:

A molecule is superimposable on its mirror image is called achiral molecule.

Answer 15

(E)

Interpretation Introduction

Interpretation:

The possible stereoisomer’s has to be shown if the product is chiral.

Concept introduction:

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

Achiral:

A molecule is superimposable on its mirror image is called achiral molecule.

Answer 16

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Ch. 23.1 - Prob. 23.1P Ch. 23.2 - Prob. 23.2P Ch. 23.2 - Prob. 23.3P Ch. 23.2 - Prob. 23.4P Ch. 23.5 - Prob. 23.5P Ch. 23.5 - Prob. AQ Ch. 23.5 - What is the hybridization of the nitrogen in...Ch. 23.5 - Prob. CQ Ch. 23.5 - The pKas of the conjugate acids of aniline and...Ch. 23.5 - Prob. EQ

Interpretation: The reagent and condition is to be proposed for step 2 and step 3. Concept introduction: Oxime formation: Aldehyde or ketone is reaction with hydroxylamine and sodium methoxide which yields oxime

Interpretation: The reagent and condition is to be proposed for step 4 and step 5. Concept introduction: Reduction: Aldehydes or ketones undergoing reduction by using reducing agent like LAH or NaBH4 which provides alcohol.

Chapter 23 Solutions

Interpretation:

The reagent and condition is to be proposed for step 2 and step 3.

Concept introduction:

Oxime formation: Aldehyde or ketone is reaction with hydroxylamine and sodium methoxide which yields oxime

Interpretation:

The reagent and condition is to be proposed for step 4 and step 5.

Concept introduction:

Reduction: Aldehydes or ketones undergoing reduction by using reducing agent like LAH or NaBH₄ which provides alcohol.