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

Please identify the reagents used in the synthetic scheme shown below. You should choose reagents that accomplish the reactions and do not result in undesired side reactions. You may use a 1-carbon reagent. Please briefly explain the reasoning for your choice of reagent 1 in the first synthesis step.

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 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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Please identify the reagents used in the synthetic scheme shown below. You should choose reagents that accomplish the reactions and do not result in undesired side reactions. You may use a 1-carbon reagent. Please briefly explain the reasoning for your choice of reagent 1 in the first synthesis step.

H2N. 1)? 2)? 3)? Choose the correct reagents from the following list: A D CH;CL, AICI, Zn, HCI CH,COCL AICI, Zn(Hg), HCI, heat H. Bry AIBry KMnO NaOH, heat HNO, H,SO. H,O Enter the correct letter for each step of the reaction in the boxes below. (Reagents cannot be used more than once)

In each reaction box, place the best reagent and conditions from the list provided. 1) Br 2) 3) 4) DEET (the active ingredient in over the counter insect repellant) 5) Answer Bank Mg, Et,0 HN(CH, CH, ), (1 equiv.) H,O* CH,COOH CH,CH,NH, CH,CH, Br NH(CH,CH,),(2 cquiv.) НСООСH, H,CO НСООН CH, CH, OH NaCN NaNH, Br,, FeBr, SOCI, CO,

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 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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See solution

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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 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

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

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 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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See solution

Check out sample textbook solution

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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