a) Interpretation: The flaw in the synthetic scheme given is to be identified. Concept introduction: Alkyl halides when treated with cyanides yield nitriles which upon hydrolysis give carboxylic acids. Grignard reagents will add on to the triple bond in nitriles. To identify: The flaw in the synthetic scheme given.

Question

Fill in the missing reagents and chemical structures in the following synthetic proposal.

Answer 1

Question

Chapter 20.SE, Problem 59AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Alkyl halides when treated with cyanides yield nitriles which upon hydrolysis give carboxylic acids. Grignard reagents will add on to the triple bond in nitriles.

To identify:

The flaw in the synthetic scheme given.

Interpretation Introduction

b)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Carboxylic acids are reduced to alcohols and not to alkanes by LiAlH₄.

To identify:

The flaw in the synthetic scheme given.

Interpretation Introduction

c)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Alkyl halides when treated with cyanides yield nitriles which upon hydrolysis give carboxylic acids. Tertiary alcohols get dehydrate to yield alkenes when treated with aqueous acids.

To identify:

The flaw in the synthetic scheme given.

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Fill in the missing reagents and chemical structures in the following synthetic proposal.

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Answer 2

Question

Chapter 20.SE, Problem 59AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Alkyl halides when treated with cyanides yield nitriles which upon hydrolysis give carboxylic acids. Grignard reagents will add on to the triple bond in nitriles.

To identify:

The flaw in the synthetic scheme given.

Interpretation Introduction

b)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Carboxylic acids are reduced to alcohols and not to alkanes by LiAlH₄.

To identify:

The flaw in the synthetic scheme given.

Interpretation Introduction

c)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Alkyl halides when treated with cyanides yield nitriles which upon hydrolysis give carboxylic acids. Tertiary alcohols get dehydrate to yield alkenes when treated with aqueous acids.

To identify:

The flaw in the synthetic scheme given.

Expert Solution & Answer

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Answer 3

Question

Chapter 20.SE, Problem 59AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Alkyl halides when treated with cyanides yield nitriles which upon hydrolysis give carboxylic acids. Grignard reagents will add on to the triple bond in nitriles.

To identify:

The flaw in the synthetic scheme given.

Interpretation Introduction

b)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Carboxylic acids are reduced to alcohols and not to alkanes by LiAlH₄.

To identify:

The flaw in the synthetic scheme given.

Interpretation Introduction

c)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Alkyl halides when treated with cyanides yield nitriles which upon hydrolysis give carboxylic acids. Tertiary alcohols get dehydrate to yield alkenes when treated with aqueous acids.

To identify:

The flaw in the synthetic scheme given.

Expert Solution & Answer

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Answer 4

Question

Chapter 20.SE, Problem 59AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Alkyl halides when treated with cyanides yield nitriles which upon hydrolysis give carboxylic acids. Grignard reagents will add on to the triple bond in nitriles.

To identify:

The flaw in the synthetic scheme given.

Interpretation Introduction

b)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Carboxylic acids are reduced to alcohols and not to alkanes by LiAlH₄.

To identify:

The flaw in the synthetic scheme given.

Interpretation Introduction

c)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Alkyl halides when treated with cyanides yield nitriles which upon hydrolysis give carboxylic acids. Tertiary alcohols get dehydrate to yield alkenes when treated with aqueous acids.

To identify:

The flaw in the synthetic scheme given.

Expert Solution & Answer

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Answer 5

Chapter 20.SE, Problem 59AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Alkyl halides when treated with cyanides yield nitriles which upon hydrolysis give carboxylic acids. Grignard reagents will add on to the triple bond in nitriles.

To identify:

The flaw in the synthetic scheme given.

Interpretation Introduction

b)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Carboxylic acids are reduced to alcohols and not to alkanes by LiAlH₄.

To identify:

The flaw in the synthetic scheme given.

Interpretation Introduction

c)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Alkyl halides when treated with cyanides yield nitriles which upon hydrolysis give carboxylic acids. Tertiary alcohols get dehydrate to yield alkenes when treated with aqueous acids.

To identify:

The flaw in the synthetic scheme given.

Answer 6

Chapter 20.SE, Problem 59AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Alkyl halides when treated with cyanides yield nitriles which upon hydrolysis give carboxylic acids. Grignard reagents will add on to the triple bond in nitriles.

To identify:

The flaw in the synthetic scheme given.

Answer 7

Chapter 20.SE, Problem 59AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Alkyl halides when treated with cyanides yield nitriles which upon hydrolysis give carboxylic acids. Grignard reagents will add on to the triple bond in nitriles.

To identify:

The flaw in the synthetic scheme given.

Answer 8

Interpretation Introduction

b)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Carboxylic acids are reduced to alcohols and not to alkanes by LiAlH₄.

To identify:

The flaw in the synthetic scheme given.

Answer 9

Interpretation Introduction

b)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Carboxylic acids are reduced to alcohols and not to alkanes by LiAlH₄.

To identify:

The flaw in the synthetic scheme given.

Answer 10

Interpretation Introduction

c)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Alkyl halides when treated with cyanides yield nitriles which upon hydrolysis give carboxylic acids. Tertiary alcohols get dehydrate to yield alkenes when treated with aqueous acids.

To identify:

The flaw in the synthetic scheme given.

Answer 11

Interpretation Introduction

c)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Alkyl halides when treated with cyanides yield nitriles which upon hydrolysis give carboxylic acids. Tertiary alcohols get dehydrate to yield alkenes when treated with aqueous acids.

To identify:

The flaw in the synthetic scheme given.

Answer 12

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Answer 13

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Answer 23

Ch. 20.1 - Give IUPAC names for the following compounds:Ch. 20.1 - Draw structures corresponding to the following...Ch. 20.2 - Prob. 3P Ch. 20.2 - The Ka for dichloroacetic acid is 3.32 Ă— 10-2....Ch. 20.3 - Calculate the percentages of dissociated and...Ch. 20.4 - Which would you expect to be a stronger acid, the...Ch. 20.4 - Dicarboxylic acids have two dissociation...Ch. 20.4 - The pKa of p-cyclopropylbenzoic acid is 4.45. Is...Ch. 20.4 - Prob. 9P Ch. 20.5 - Prob. 10P

Solution Summary: The author explains that the flaw in the synthetic scheme is that when reduced with LiAlH4, carboxyl group is converted into a primary alcohol.

b)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Carboxylic acids are reduced to alcohols and not to alkanes by LiAlH₄.

To identify:

The flaw in the synthetic scheme given.

Chapter 20 Solutions

Solution Summary: The author explains that the flaw in the synthetic scheme is that when reduced with LiAlH4, carboxyl group is converted into a primary alcohol.

b) Interpretation: The flaw in the synthetic scheme given is to be identified. Concept introduction: Carboxylic acids are reduced to alcohols and not to alkanes by LiAlH4. To identify: The flaw in the synthetic scheme given.

Chapter 20 Solutions

b)

Interpretation:

The flaw in the synthetic scheme given is to be identified.

Concept introduction:

Carboxylic acids are reduced to alcohols and not to alkanes by LiAlH₄.

To identify:

The flaw in the synthetic scheme given.