a) Interpretation: The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with malonic ester, a nucleophilic donor 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 Î±,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 Î±-carbon of the donor and the β- carbon of the unsaturated acceptor. To give: The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with malonic ester, a nucleophilic donor.

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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 17P

Interpretation Introduction

a)

Interpretation:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with malonic ester, a nucleophilic donor 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 Î±,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 Î±-carbon of the donor and the β- carbon of the unsaturated acceptor.

To give:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with malonic ester, a nucleophilic donor.

Interpretation Introduction

b)

Interpretation:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with the β- keto ester, a nucleophilic donor shown 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 Î±,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 Î±-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with the β- keto ester, a nucleophilic donor shown.

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(11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B Bond A Bond C a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. Weakest Bond Strongest Bond b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. c. (5pts) Use principles discussed in lecture, supported by relevant structures, to succinctly explain the why your part b (i) radical is more stable than your part b(ii) radical. Written explanation can be no more than one-two succinct sentence(s)!

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 17P

Interpretation Introduction

a)

Interpretation:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with malonic ester, a nucleophilic donor 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 Î±,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 Î±-carbon of the donor and the β- carbon of the unsaturated acceptor.

To give:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with malonic ester, a nucleophilic donor.

Interpretation Introduction

b)

Interpretation:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with the β- keto ester, a nucleophilic donor shown 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 Î±,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 Î±-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with the β- keto ester, a nucleophilic donor shown.

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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 17P

Interpretation Introduction

a)

Interpretation:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with malonic ester, a nucleophilic donor 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 Î±,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 Î±-carbon of the donor and the β- carbon of the unsaturated acceptor.

To give:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with malonic ester, a nucleophilic donor.

Interpretation Introduction

b)

Interpretation:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with the β- keto ester, a nucleophilic donor shown 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 Î±,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 Î±-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with the β- keto ester, a nucleophilic donor shown.

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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 17P

Interpretation Introduction

a)

Interpretation:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with malonic ester, a nucleophilic donor 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 Î±,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 Î±-carbon of the donor and the β- carbon of the unsaturated acceptor.

To give:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with malonic ester, a nucleophilic donor.

Interpretation Introduction

b)

Interpretation:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with the β- keto ester, a nucleophilic donor shown 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 Î±,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 Î±-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with the β- keto ester, a nucleophilic donor shown.

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Answer 5

Chapter 23.10, Problem 17P

Interpretation Introduction

a)

Interpretation:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with malonic ester, a nucleophilic donor 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 Î±,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 Î±-carbon of the donor and the β- carbon of the unsaturated acceptor.

To give:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with malonic ester, a nucleophilic donor.

Interpretation Introduction

b)

Interpretation:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with the β- keto ester, a nucleophilic donor shown 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 Î±,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 Î±-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with the β- keto ester, a nucleophilic donor shown.

Answer 6

Chapter 23.10, Problem 17P

Interpretation Introduction

a)

Interpretation:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with malonic ester, a nucleophilic donor 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 Î±,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 Î±-carbon of the donor and the β- carbon of the unsaturated acceptor.

To give:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with malonic ester, a nucleophilic donor.

Answer 7

Chapter 23.10, Problem 17P

Interpretation Introduction

a)

Interpretation:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with malonic ester, a nucleophilic donor 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 Î±,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 Î±-carbon of the donor and the β- carbon of the unsaturated acceptor.

To give:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with malonic ester, a nucleophilic donor.

Answer 8

Interpretation Introduction

b)

Interpretation:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with the β- keto ester, a nucleophilic donor shown 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 Î±,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 Î±-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with the β- keto ester, a nucleophilic donor shown.

Answer 9

Interpretation Introduction

b)

Interpretation:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with the β- keto ester, a nucleophilic donor shown 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 Î±,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 Î±-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 3-buten-2-one with the β- keto ester, a nucleophilic donor shown.

Answer 10

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Answer 11

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Answer 12

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Answer 13

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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