a) Interpretation: The flaw in the reaction scheme given is to be identified and the corrected scheme is to be provided. Concept introduction: α,β-Unsaturated ketones when treated with Grignard reagents yield a product with the 1,2-addition of RH to the C = O bond in the ketone to yield a tertiary alcohol. The C = O group in ketones is reduced to a secondary alcohol by LiAlH 4 . To identify: The flaw in the reaction scheme given and to provide the corrected scheme.

Question

The following reaction scheme contains one or more flaws. Explain what is wrong in each of the following reaction schemes and suggest how you would correct the scheme.

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 19.SE, Problem 76AP

Interpretation Introduction

a)

Interpretation:

The flaw in the reaction scheme given is to be identified and the corrected scheme is to be provided.

Concept introduction:

α,β-Unsaturated ketones when treated with Grignard reagents yield a product with the 1,2-addition of RH to the C = O bond in the ketone to yield a tertiary alcohol. The C = O group in ketones is reduced to a secondary alcohol by LiAlH₄.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Interpretation Introduction

b)

Interpretation:

The flaw in the reaction scheme given is to be identified and corrected scheme is to be given.

Concept introduction:

CrO₃ in the presence of H₃O⁺ oxidize primary alcohols to acids and not to aldehydes. Aldehyde can be converted into an acetal by treating with methanol in the presence of acids.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Interpretation Introduction

c)

Interpretation:

The flaw in the reaction scheme given is to be identified and corrected scheme is to be given.

Concept introduction:

Aldehydes and ketones react with HCN, KCN to yield the corresponding cyanohydrins. The cyanohydrins when treated with aqueous acids will get hydrolysed to acids.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

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The following reaction scheme contains one or more flaws. Explain what is wrong in each of the following reaction schemes and suggest how you would correct the scheme.

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Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 19.SE, Problem 76AP

Interpretation Introduction

a)

Interpretation:

The flaw in the reaction scheme given is to be identified and the corrected scheme is to be provided.

Concept introduction:

α,β-Unsaturated ketones when treated with Grignard reagents yield a product with the 1,2-addition of RH to the C = O bond in the ketone to yield a tertiary alcohol. The C = O group in ketones is reduced to a secondary alcohol by LiAlH₄.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Interpretation Introduction

b)

Interpretation:

The flaw in the reaction scheme given is to be identified and corrected scheme is to be given.

Concept introduction:

CrO₃ in the presence of H₃O⁺ oxidize primary alcohols to acids and not to aldehydes. Aldehyde can be converted into an acetal by treating with methanol in the presence of acids.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Interpretation Introduction

c)

Interpretation:

The flaw in the reaction scheme given is to be identified and corrected scheme is to be given.

Concept introduction:

Aldehydes and ketones react with HCN, KCN to yield the corresponding cyanohydrins. The cyanohydrins when treated with aqueous acids will get hydrolysed to acids.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Expert Solution & Answer

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Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 19.SE, Problem 76AP

Interpretation Introduction

a)

Interpretation:

The flaw in the reaction scheme given is to be identified and the corrected scheme is to be provided.

Concept introduction:

α,β-Unsaturated ketones when treated with Grignard reagents yield a product with the 1,2-addition of RH to the C = O bond in the ketone to yield a tertiary alcohol. The C = O group in ketones is reduced to a secondary alcohol by LiAlH₄.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Interpretation Introduction

b)

Interpretation:

The flaw in the reaction scheme given is to be identified and corrected scheme is to be given.

Concept introduction:

CrO₃ in the presence of H₃O⁺ oxidize primary alcohols to acids and not to aldehydes. Aldehyde can be converted into an acetal by treating with methanol in the presence of acids.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Interpretation Introduction

c)

Interpretation:

The flaw in the reaction scheme given is to be identified and corrected scheme is to be given.

Concept introduction:

Aldehydes and ketones react with HCN, KCN to yield the corresponding cyanohydrins. The cyanohydrins when treated with aqueous acids will get hydrolysed to acids.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Expert Solution & Answer

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Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 19.SE, Problem 76AP

Interpretation Introduction

a)

Interpretation:

The flaw in the reaction scheme given is to be identified and the corrected scheme is to be provided.

Concept introduction:

α,β-Unsaturated ketones when treated with Grignard reagents yield a product with the 1,2-addition of RH to the C = O bond in the ketone to yield a tertiary alcohol. The C = O group in ketones is reduced to a secondary alcohol by LiAlH₄.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Interpretation Introduction

b)

Interpretation:

The flaw in the reaction scheme given is to be identified and corrected scheme is to be given.

Concept introduction:

CrO₃ in the presence of H₃O⁺ oxidize primary alcohols to acids and not to aldehydes. Aldehyde can be converted into an acetal by treating with methanol in the presence of acids.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Interpretation Introduction

c)

Interpretation:

The flaw in the reaction scheme given is to be identified and corrected scheme is to be given.

Concept introduction:

Aldehydes and ketones react with HCN, KCN to yield the corresponding cyanohydrins. The cyanohydrins when treated with aqueous acids will get hydrolysed to acids.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Expert Solution & Answer

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Answer 5

Chapter 19.SE, Problem 76AP

Interpretation Introduction

a)

Interpretation:

The flaw in the reaction scheme given is to be identified and the corrected scheme is to be provided.

Concept introduction:

α,β-Unsaturated ketones when treated with Grignard reagents yield a product with the 1,2-addition of RH to the C = O bond in the ketone to yield a tertiary alcohol. The C = O group in ketones is reduced to a secondary alcohol by LiAlH₄.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Interpretation Introduction

b)

Interpretation:

The flaw in the reaction scheme given is to be identified and corrected scheme is to be given.

Concept introduction:

CrO₃ in the presence of H₃O⁺ oxidize primary alcohols to acids and not to aldehydes. Aldehyde can be converted into an acetal by treating with methanol in the presence of acids.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Interpretation Introduction

c)

Interpretation:

The flaw in the reaction scheme given is to be identified and corrected scheme is to be given.

Concept introduction:

Aldehydes and ketones react with HCN, KCN to yield the corresponding cyanohydrins. The cyanohydrins when treated with aqueous acids will get hydrolysed to acids.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Answer 6

Chapter 19.SE, Problem 76AP

Interpretation Introduction

a)

Interpretation:

The flaw in the reaction scheme given is to be identified and the corrected scheme is to be provided.

Concept introduction:

α,β-Unsaturated ketones when treated with Grignard reagents yield a product with the 1,2-addition of RH to the C = O bond in the ketone to yield a tertiary alcohol. The C = O group in ketones is reduced to a secondary alcohol by LiAlH₄.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Answer 7

Chapter 19.SE, Problem 76AP

Interpretation Introduction

a)

Interpretation:

The flaw in the reaction scheme given is to be identified and the corrected scheme is to be provided.

Concept introduction:

α,β-Unsaturated ketones when treated with Grignard reagents yield a product with the 1,2-addition of RH to the C = O bond in the ketone to yield a tertiary alcohol. The C = O group in ketones is reduced to a secondary alcohol by LiAlH₄.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Answer 8

Interpretation Introduction

b)

Interpretation:

The flaw in the reaction scheme given is to be identified and corrected scheme is to be given.

Concept introduction:

CrO₃ in the presence of H₃O⁺ oxidize primary alcohols to acids and not to aldehydes. Aldehyde can be converted into an acetal by treating with methanol in the presence of acids.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Answer 9

Interpretation Introduction

b)

Interpretation:

The flaw in the reaction scheme given is to be identified and corrected scheme is to be given.

Concept introduction:

CrO₃ in the presence of H₃O⁺ oxidize primary alcohols to acids and not to aldehydes. Aldehyde can be converted into an acetal by treating with methanol in the presence of acids.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Answer 10

Interpretation Introduction

c)

Interpretation:

The flaw in the reaction scheme given is to be identified and corrected scheme is to be given.

Concept introduction:

Aldehydes and ketones react with HCN, KCN to yield the corresponding cyanohydrins. The cyanohydrins when treated with aqueous acids will get hydrolysed to acids.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Answer 11

Interpretation Introduction

c)

Interpretation:

The flaw in the reaction scheme given is to be identified and corrected scheme is to be given.

Concept introduction:

Aldehydes and ketones react with HCN, KCN to yield the corresponding cyanohydrins. The cyanohydrins when treated with aqueous acids will get hydrolysed to acids.

To identify:

The flaw in the reaction scheme given and to provide the corrected scheme.

Answer 12

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Answer 23

Ch. 19.1 - Prob. 1P Ch. 19.1 - Draw structures corresponding to the following...Ch. 19.2 - Prob. 3P Ch. 19.2 - How would you carry out the following reactions?...Ch. 19.4 - Treatment of an aldehyde or ketone with cyanide...Ch. 19.4 - p-Nitrobenzaldehyde is more reactive toward...Ch. 19.5 - Prob. 7P Ch. 19.5 - The oxygen in water is primarily (99.8) 16O, but...Ch. 19.6 - Prob. 9P Ch. 19.8 - Show the products you would obtain by...

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