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

A benzene ring alters the reactivity of a neighboring group in the so-called “benzylic” position, similarly to how a double bond alters the reactivity of groups in the “allylic” position. Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates. a) Use resonance structures to show the delocalization of the positive charge, negative charge, and unpaired electron of the benzyl cation, anion, and radical.

Answer 1

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

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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A benzene ring alters the reactivity of a neighboring group in the so-called “benzylic” position, similarly to how a double bond alters the reactivity of groups in the “allylic” position. Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates. a) Use resonance structures to show the delocalization of the positive charge, negative charge, and unpaired electron of the benzyl cation, anion, and radical.

The following compounds have the same molecular formula as benzene. How many monobrominated products could each form? a. How many dibrominated products could each of the preceding compounds form? (Do not include stereoisomers.) b. How many dibrominated products could each of the compounds form if stereoisomers are included?

a. The following compounds have the same molecular formula as benzene. How many monobrominated products could each form? 1. HC‚CC‚CCH2CH3 2. CH2“CHC‚CCH“CH2 b. How many dibrominated products could each of the preceding compounds form? (Do not include stereoisomers.) c. How many dibrominated products could each of the compounds form if stereoisomers are included?

Answer 2

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

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

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

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

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

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

Expert Solution & Answer

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.