a) 2-cyclohexanone Interpretation: The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with 2-cyclohexanone (α, β- unsaturated acceptor) is to be given. Concept introduction: Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester. To give: The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with 2-cyclohexanone (α, β- unsaturated acceptor).

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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 23.10, Problem 16P

Interpretation Introduction

a) 2-cyclohexanone

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with 2-cyclohexanone (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with 2-cyclohexanone (α, β- unsaturated acceptor).

Interpretation Introduction

b) Propenenitrile

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with propenenitrile (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with propenenitrile (α, β- unsaturated acceptor).

Interpretation Introduction

c) Ethyl-2-butenoate

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with ethyl-2-butenoate (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with ethyl-2-butenoate (α, β- unsaturated acceptor).

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Which of the following species is a valid resonance structure of A? Use curved arrows to show how A is converted to any valid resonance structure. When a compound is not a valid resonance structurc of A, explain why not. Provide steps and tips on what to look for to understand how to solve and apply to other problems.

N IZ Check the box under each structure in the table that is an enantiomer of the molecule shown below. If none of them are, check the none of the above box under the table. Molecule 1 Molecule 2 HN Molecule 3 Х HN www. Molecule 4 Molecule 5 Molecule 6 none of the above NH NH G

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Answer 2

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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 23.10, Problem 16P

Interpretation Introduction

a) 2-cyclohexanone

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with 2-cyclohexanone (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with 2-cyclohexanone (α, β- unsaturated acceptor).

Interpretation Introduction

b) Propenenitrile

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with propenenitrile (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with propenenitrile (α, β- unsaturated acceptor).

Interpretation Introduction

c) Ethyl-2-butenoate

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with ethyl-2-butenoate (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with ethyl-2-butenoate (α, β- unsaturated acceptor).

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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 23.10, Problem 16P

Interpretation Introduction

a) 2-cyclohexanone

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with 2-cyclohexanone (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with 2-cyclohexanone (α, β- unsaturated acceptor).

Interpretation Introduction

b) Propenenitrile

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with propenenitrile (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with propenenitrile (α, β- unsaturated acceptor).

Interpretation Introduction

c) Ethyl-2-butenoate

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with ethyl-2-butenoate (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with ethyl-2-butenoate (α, β- unsaturated acceptor).

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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 23.10, Problem 16P

Interpretation Introduction

a) 2-cyclohexanone

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with 2-cyclohexanone (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with 2-cyclohexanone (α, β- unsaturated acceptor).

Interpretation Introduction

b) Propenenitrile

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with propenenitrile (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with propenenitrile (α, β- unsaturated acceptor).

Interpretation Introduction

c) Ethyl-2-butenoate

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with ethyl-2-butenoate (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with ethyl-2-butenoate (α, β- unsaturated acceptor).

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Answer 5

Chapter 23.10, Problem 16P

Interpretation Introduction

a) 2-cyclohexanone

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with 2-cyclohexanone (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with 2-cyclohexanone (α, β- unsaturated acceptor).

Interpretation Introduction

b) Propenenitrile

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with propenenitrile (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with propenenitrile (α, β- unsaturated acceptor).

Interpretation Introduction

c) Ethyl-2-butenoate

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with ethyl-2-butenoate (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with ethyl-2-butenoate (α, β- unsaturated acceptor).

Answer 6

Chapter 23.10, Problem 16P

Interpretation Introduction

a) 2-cyclohexanone

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with 2-cyclohexanone (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with 2-cyclohexanone (α, β- unsaturated acceptor).

Answer 7

Chapter 23.10, Problem 16P

Interpretation Introduction

a) 2-cyclohexanone

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with 2-cyclohexanone (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with 2-cyclohexanone (α, β- unsaturated acceptor).

Answer 8

Interpretation Introduction

b) Propenenitrile

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with propenenitrile (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with propenenitrile (α, β- unsaturated acceptor).

Answer 9

Interpretation Introduction

b) Propenenitrile

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with propenenitrile (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with propenenitrile (α, β- unsaturated acceptor).

Answer 10

Interpretation Introduction

c) Ethyl-2-butenoate

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with ethyl-2-butenoate (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with ethyl-2-butenoate (α, β- unsaturated acceptor).

Answer 11

Interpretation Introduction

c) Ethyl-2-butenoate

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with ethyl-2-butenoate (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with ethyl-2-butenoate (α, β- unsaturated acceptor).

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 23.1 - Prob. 1P Ch. 23.1 - Prob. 2P Ch. 23.3 - Prob. 3P Ch. 23.3 - Prob. 4P Ch. 23.4 - Prob. 5P Ch. 23.4 - 1-Butanol is prepared commercially by a route that...Ch. 23.4 - Prob. 7P Ch. 23.5 - Prob. 8P Ch. 23.6 - Prob. 9P Ch. 23.6 - What product would you Expect to obtain from base...

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