(a) Interpretation: How would you carry out the following synthesis is to be suggested. Concept introduction: Synthesis of the target molecule is achieved through different chemical reactions involving either reactions that alter the carbon skeleton or the functional group transformation reactions. By observing the target and the given starting compound, the synthesis is planned. Alkylation of ketone leads to form a new C-C bond at α position. For alkylation reaction of ketone, a strong base like NaOH is used to deprotonate the alpha hydrogen atom which leads to form an enolate ion. This is followed by reaction of this enolate with alkyl halide to add the desired number of carbon atoms at the alpha position of the original ketone. This alkylated product undergoes an acid-catalyzed halogenation reaction in presence of X 2 and acetic acid ( CH 3 COOH ) which results in the formation of C-X bond at more substituted α carbon atom. Dehydrohalogenation reaction leads to the formation of C=C from halo alkane. This reaction is carried out in the presence of a strong base like CH 3 ONa and heat.

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Question

Chapter 13, Problem 13.48P

Interpretation Introduction

(a)

Interpretation:

How would you carry out the following synthesis is to be suggested.

Concept introduction:

Synthesis of the target molecule is achieved through different chemical reactions involving either reactions that alter the carbon skeleton or the functional group transformation reactions. By observing the target and the given starting compound, the synthesis is planned.

Alkylation of ketone leads to form a new C-C bond at α position. For alkylation reaction of ketone, a strong base like NaOH is used to deprotonate the alpha hydrogen atom which leads to form an enolate ion. This is followed by reaction of this enolate with alkyl halide to add the desired number of carbon atoms at the alpha position of the original ketone.

This alkylated product undergoes an acid-catalyzed halogenation reaction in presence of X2 and acetic acid (CH3COOH) which results in the formation of C-X bond at more substituted α carbon atom. Dehydrohalogenation reaction leads to the formation of C=C from halo alkane. This reaction is carried out in the presence of a strong base like CH3ONa and heat.

Interpretation Introduction

(b)

Interpretation:

How would you carry out the following synthesis is to be suggested.

Concept introduction:

Synthesis of target molecule is achieved through different chemical reactions involving either reactions that alter the carbon skeleton or the functional group transformation reactions. By observing the target and the given starting compound, the synthesis is planned.

Alkylation of ketone leads to the formation of a new C-C bond at α position. For alkylation reaction of ketone a strong base like NaOH is used to deprotonate the alpha hydrogen atom which leads to form an enolate ion. This is followed by the reaction of this enolate with alkyl halide to add the desired number of carbon atoms at the alpha position of the original ketone.

This alkylated product undergoes a base-catalyzed halogenation reaction in presence of X2 and LDA. This results in the formation of a new C-X bond at the less substituted α carbon atom of the ketone. Dehydrohalogenation reaction leads to the formation of C=C from halo alkane. This reaction is carried out in presence of strong base like CH3ONa and heat.

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Shown below is the mechanism presented for the formation of biasplatin in reference 1 from the Background and Experiment document. The amounts used of each reactant are shown. Either draw or describe a better alternative to this mechanism. (Note that the first step represents two steps combined and the proton loss is not even shown; fixing these is not the desired improvement.) (Hints: The first step is correct, the second step is not; and the amount of the anhydride is in large excess to serve a purpose.)

Answer 2

Question

Chapter 13, Problem 13.48P

Interpretation Introduction

(a)

Interpretation:

How would you carry out the following synthesis is to be suggested.

Concept introduction:

Synthesis of the target molecule is achieved through different chemical reactions involving either reactions that alter the carbon skeleton or the functional group transformation reactions. By observing the target and the given starting compound, the synthesis is planned.

Alkylation of ketone leads to form a new C-C bond at α position. For alkylation reaction of ketone, a strong base like NaOH is used to deprotonate the alpha hydrogen atom which leads to form an enolate ion. This is followed by reaction of this enolate with alkyl halide to add the desired number of carbon atoms at the alpha position of the original ketone.

This alkylated product undergoes an acid-catalyzed halogenation reaction in presence of X2 and acetic acid (CH3COOH) which results in the formation of C-X bond at more substituted α carbon atom. Dehydrohalogenation reaction leads to the formation of C=C from halo alkane. This reaction is carried out in the presence of a strong base like CH3ONa and heat.

Interpretation Introduction

(b)

Interpretation:

How would you carry out the following synthesis is to be suggested.

Concept introduction:

Synthesis of target molecule is achieved through different chemical reactions involving either reactions that alter the carbon skeleton or the functional group transformation reactions. By observing the target and the given starting compound, the synthesis is planned.

Alkylation of ketone leads to the formation of a new C-C bond at α position. For alkylation reaction of ketone a strong base like NaOH is used to deprotonate the alpha hydrogen atom which leads to form an enolate ion. This is followed by the reaction of this enolate with alkyl halide to add the desired number of carbon atoms at the alpha position of the original ketone.

This alkylated product undergoes a base-catalyzed halogenation reaction in presence of X2 and LDA. This results in the formation of a new C-X bond at the less substituted α carbon atom of the ketone. Dehydrohalogenation reaction leads to the formation of C=C from halo alkane. This reaction is carried out in presence of strong base like CH3ONa and heat.

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Answer 3

Question

Chapter 13, Problem 13.48P

Interpretation Introduction

(a)

Interpretation:

How would you carry out the following synthesis is to be suggested.

Concept introduction:

Synthesis of the target molecule is achieved through different chemical reactions involving either reactions that alter the carbon skeleton or the functional group transformation reactions. By observing the target and the given starting compound, the synthesis is planned.

Alkylation of ketone leads to form a new C-C bond at α position. For alkylation reaction of ketone, a strong base like NaOH is used to deprotonate the alpha hydrogen atom which leads to form an enolate ion. This is followed by reaction of this enolate with alkyl halide to add the desired number of carbon atoms at the alpha position of the original ketone.

This alkylated product undergoes an acid-catalyzed halogenation reaction in presence of X2 and acetic acid (CH3COOH) which results in the formation of C-X bond at more substituted α carbon atom. Dehydrohalogenation reaction leads to the formation of C=C from halo alkane. This reaction is carried out in the presence of a strong base like CH3ONa and heat.

Interpretation Introduction

(b)

Interpretation:

How would you carry out the following synthesis is to be suggested.

Concept introduction:

Synthesis of target molecule is achieved through different chemical reactions involving either reactions that alter the carbon skeleton or the functional group transformation reactions. By observing the target and the given starting compound, the synthesis is planned.

Alkylation of ketone leads to the formation of a new C-C bond at α position. For alkylation reaction of ketone a strong base like NaOH is used to deprotonate the alpha hydrogen atom which leads to form an enolate ion. This is followed by the reaction of this enolate with alkyl halide to add the desired number of carbon atoms at the alpha position of the original ketone.

This alkylated product undergoes a base-catalyzed halogenation reaction in presence of X2 and LDA. This results in the formation of a new C-X bond at the less substituted α carbon atom of the ketone. Dehydrohalogenation reaction leads to the formation of C=C from halo alkane. This reaction is carried out in presence of strong base like CH3ONa and heat.

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Answer 4

Question

Chapter 13, Problem 13.48P

Interpretation Introduction

(a)

Interpretation:

How would you carry out the following synthesis is to be suggested.

Concept introduction:

Synthesis of the target molecule is achieved through different chemical reactions involving either reactions that alter the carbon skeleton or the functional group transformation reactions. By observing the target and the given starting compound, the synthesis is planned.

Alkylation of ketone leads to form a new C-C bond at α position. For alkylation reaction of ketone, a strong base like NaOH is used to deprotonate the alpha hydrogen atom which leads to form an enolate ion. This is followed by reaction of this enolate with alkyl halide to add the desired number of carbon atoms at the alpha position of the original ketone.

This alkylated product undergoes an acid-catalyzed halogenation reaction in presence of X2 and acetic acid (CH3COOH) which results in the formation of C-X bond at more substituted α carbon atom. Dehydrohalogenation reaction leads to the formation of C=C from halo alkane. This reaction is carried out in the presence of a strong base like CH3ONa and heat.

Interpretation Introduction

(b)

Interpretation:

How would you carry out the following synthesis is to be suggested.

Concept introduction:

Synthesis of target molecule is achieved through different chemical reactions involving either reactions that alter the carbon skeleton or the functional group transformation reactions. By observing the target and the given starting compound, the synthesis is planned.

Alkylation of ketone leads to the formation of a new C-C bond at α position. For alkylation reaction of ketone a strong base like NaOH is used to deprotonate the alpha hydrogen atom which leads to form an enolate ion. This is followed by the reaction of this enolate with alkyl halide to add the desired number of carbon atoms at the alpha position of the original ketone.

This alkylated product undergoes a base-catalyzed halogenation reaction in presence of X2 and LDA. This results in the formation of a new C-X bond at the less substituted α carbon atom of the ketone. Dehydrohalogenation reaction leads to the formation of C=C from halo alkane. This reaction is carried out in presence of strong base like CH3ONa and heat.

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Answer 5

Chapter 13, Problem 13.48P

Interpretation Introduction

(a)

Interpretation:

How would you carry out the following synthesis is to be suggested.

Concept introduction:

Synthesis of the target molecule is achieved through different chemical reactions involving either reactions that alter the carbon skeleton or the functional group transformation reactions. By observing the target and the given starting compound, the synthesis is planned.

Alkylation of ketone leads to form a new C-C bond at α position. For alkylation reaction of ketone, a strong base like NaOH is used to deprotonate the alpha hydrogen atom which leads to form an enolate ion. This is followed by reaction of this enolate with alkyl halide to add the desired number of carbon atoms at the alpha position of the original ketone.

This alkylated product undergoes an acid-catalyzed halogenation reaction in presence of X2 and acetic acid (CH3COOH) which results in the formation of C-X bond at more substituted α carbon atom. Dehydrohalogenation reaction leads to the formation of C=C from halo alkane. This reaction is carried out in the presence of a strong base like CH3ONa and heat.

Interpretation Introduction

(b)

Interpretation:

How would you carry out the following synthesis is to be suggested.

Concept introduction:

Synthesis of target molecule is achieved through different chemical reactions involving either reactions that alter the carbon skeleton or the functional group transformation reactions. By observing the target and the given starting compound, the synthesis is planned.

Alkylation of ketone leads to the formation of a new C-C bond at α position. For alkylation reaction of ketone a strong base like NaOH is used to deprotonate the alpha hydrogen atom which leads to form an enolate ion. This is followed by the reaction of this enolate with alkyl halide to add the desired number of carbon atoms at the alpha position of the original ketone.

This alkylated product undergoes a base-catalyzed halogenation reaction in presence of X2 and LDA. This results in the formation of a new C-X bond at the less substituted α carbon atom of the ketone. Dehydrohalogenation reaction leads to the formation of C=C from halo alkane. This reaction is carried out in presence of strong base like CH3ONa and heat.

Answer 6

Chapter 13, Problem 13.48P

Interpretation Introduction

(a)

Interpretation:

How would you carry out the following synthesis is to be suggested.

Concept introduction:

Synthesis of the target molecule is achieved through different chemical reactions involving either reactions that alter the carbon skeleton or the functional group transformation reactions. By observing the target and the given starting compound, the synthesis is planned.

Alkylation of ketone leads to form a new C-C bond at α position. For alkylation reaction of ketone, a strong base like NaOH is used to deprotonate the alpha hydrogen atom which leads to form an enolate ion. This is followed by reaction of this enolate with alkyl halide to add the desired number of carbon atoms at the alpha position of the original ketone.

This alkylated product undergoes an acid-catalyzed halogenation reaction in presence of X2 and acetic acid (CH3COOH) which results in the formation of C-X bond at more substituted α carbon atom. Dehydrohalogenation reaction leads to the formation of C=C from halo alkane. This reaction is carried out in the presence of a strong base like CH3ONa and heat.

Answer 7

Chapter 13, Problem 13.48P

Interpretation Introduction

(a)

Interpretation:

How would you carry out the following synthesis is to be suggested.

Concept introduction:

Synthesis of the target molecule is achieved through different chemical reactions involving either reactions that alter the carbon skeleton or the functional group transformation reactions. By observing the target and the given starting compound, the synthesis is planned.

Alkylation of ketone leads to form a new C-C bond at α position. For alkylation reaction of ketone, a strong base like NaOH is used to deprotonate the alpha hydrogen atom which leads to form an enolate ion. This is followed by reaction of this enolate with alkyl halide to add the desired number of carbon atoms at the alpha position of the original ketone.

This alkylated product undergoes an acid-catalyzed halogenation reaction in presence of X2 and acetic acid (CH3COOH) which results in the formation of C-X bond at more substituted α carbon atom. Dehydrohalogenation reaction leads to the formation of C=C from halo alkane. This reaction is carried out in the presence of a strong base like CH3ONa and heat.

Answer 8

Interpretation Introduction

(b)

Interpretation:

How would you carry out the following synthesis is to be suggested.

Concept introduction:

Synthesis of target molecule is achieved through different chemical reactions involving either reactions that alter the carbon skeleton or the functional group transformation reactions. By observing the target and the given starting compound, the synthesis is planned.

Alkylation of ketone leads to the formation of a new C-C bond at α position. For alkylation reaction of ketone a strong base like NaOH is used to deprotonate the alpha hydrogen atom which leads to form an enolate ion. This is followed by the reaction of this enolate with alkyl halide to add the desired number of carbon atoms at the alpha position of the original ketone.

This alkylated product undergoes a base-catalyzed halogenation reaction in presence of X2 and LDA. This results in the formation of a new C-X bond at the less substituted α carbon atom of the ketone. Dehydrohalogenation reaction leads to the formation of C=C from halo alkane. This reaction is carried out in presence of strong base like CH3ONa and heat.

Answer 9

Interpretation Introduction

(b)

Interpretation:

How would you carry out the following synthesis is to be suggested.

Concept introduction:

Synthesis of target molecule is achieved through different chemical reactions involving either reactions that alter the carbon skeleton or the functional group transformation reactions. By observing the target and the given starting compound, the synthesis is planned.

Alkylation of ketone leads to the formation of a new C-C bond at α position. For alkylation reaction of ketone a strong base like NaOH is used to deprotonate the alpha hydrogen atom which leads to form an enolate ion. This is followed by the reaction of this enolate with alkyl halide to add the desired number of carbon atoms at the alpha position of the original ketone.

This alkylated product undergoes a base-catalyzed halogenation reaction in presence of X2 and LDA. This results in the formation of a new C-X bond at the less substituted α carbon atom of the ketone. Dehydrohalogenation reaction leads to the formation of C=C from halo alkane. This reaction is carried out in presence of strong base like CH3ONa and heat.

Answer 10

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Answer 13

Ch. 13 - Prob. 13.1P Ch. 13 - Prob. 13.2P Ch. 13 - Prob. 13.3P Ch. 13 - Prob. 13.4P Ch. 13 - Prob. 13.5P Ch. 13 - Prob. 13.6P Ch. 13 - Prob. 13.7P Ch. 13 - Prob. 13.8P Ch. 13 - Prob. 13.9P Ch. 13 - Prob. 13.10P

Solution Summary: The author explains how the synthesis of the target molecule is achieved through different chemical reactions involving either reactions that alter the carbon skeleton or the functional group transformation reactions.

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