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

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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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> You are trying to decide if there is a single reagent you can add that will make the following synthesis possible without any other major side products: 1. ☑ CI 2. H3O+ O Draw the missing reagent X you think will make this synthesis work in the drawing area below. If there is no reagent that will make your desired product in good yield or without complications, just check the box under the drawing area and leave it blank. Click and drag to start drawing a structure. Explanation Check ? DO 18 Ar B © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibility

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Consider a solution of 0.00304 moles of 4-nitrobenzoic acid (pKa = 3.442) dissolved in 25 mL water and titrated with 0.0991 M NaOH. Calculate the pH at the equivalence point

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 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).

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 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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Chapter 23 Solutions