(a) Interpretation: How the given synthesis can be carried out is to be suggested. Concept introduction: β -Keto esters can be synthesized in a reaction known as Claisen condensation. The α -hydrogen in an carbonyl compound is relatively acidic because of the presence of an adjacent electron withdrawing group. A strong bulky, non-nuclophilic base extracts this proton, resulting in the formation of a carbon nucleophile. The nucleophile attacks and adds to the electrophilic carbon of a carbonyl compound such as an ester to form a tetrahedral intermediate. The elimination of the original alkoxide (acyl) group from this intermediate followed by proton transfers completes the reaction, giving an α -keto ester.

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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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 21, Problem 21.89P

Interpretation Introduction

(a)

Interpretation:

How the given synthesis can be carried out is to be suggested.

Concept introduction:

β-Keto esters can be synthesized in a reaction known as Claisen condensation. The α-hydrogen in an carbonyl compound is relatively acidic because of the presence of an adjacent electron withdrawing group. A strong bulky, non-nuclophilic base extracts this proton, resulting in the formation of a carbon nucleophile. The nucleophile attacks and adds to the electrophilic carbon of a carbonyl compound such as an ester to form a tetrahedral intermediate. The elimination of the original alkoxide (acyl) group from this intermediate followed by proton transfers completes the reaction, giving an α-keto ester.

Interpretation Introduction

(a)

Interpretation:

How the given synthesis can be carried out is to be suggested.

Concept introduction:

β-Keto esters can be synthesized in a reaction known as Claisen condensation. The α-hydrogen in an carbonyl compound is relatively acidic because of the presence of an adjacent electron withdrawing group. A strong bulky, non-nuclophilic base extracts this proton, resulting in the formation of a carbon nucleophile. The nucleophile attacks and adds to the electrophilic carbon of a carbonyl compound such as an ester to form a tetrahedral intermediate. The elimination of the original alkoxide (acyl) group from this intermediate followed by proton transfers completes the reaction, giving an α-keto ester.

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Part VII. Below are the 'HNMR, 13 C-NMR, COSY 2D- NMR, and HSQC 2D-NMR (similar with HETCOR but axes are reversed) spectra of an organic compound with molecular formula C6H1003 - Assign chemical shift values to the H and c atoms of the compound. Find the structure. Show complete solutions. Predicted 1H NMR Spectrum 4.7 4.6 4.5 4.4 4.3 4.2 4.1 4.0 3.9 3.8 3.7 3.6 3.5 3.4 3.3 3.2 3.1 3.0 2.9 2.8 2.7 2.6 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 f1 (ppm) Predicted 13C NMR Spectrum 100 f1 (ppm) 30 220 210 200 190 180 170 160 150 140 130 120 110 90 80 70 -26 60 50 40 46 30 20 115 10 1.0 0.9 0.8 0 -10

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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 21, Problem 21.89P

Interpretation Introduction

(a)

Interpretation:

How the given synthesis can be carried out is to be suggested.

Concept introduction:

β-Keto esters can be synthesized in a reaction known as Claisen condensation. The α-hydrogen in an carbonyl compound is relatively acidic because of the presence of an adjacent electron withdrawing group. A strong bulky, non-nuclophilic base extracts this proton, resulting in the formation of a carbon nucleophile. The nucleophile attacks and adds to the electrophilic carbon of a carbonyl compound such as an ester to form a tetrahedral intermediate. The elimination of the original alkoxide (acyl) group from this intermediate followed by proton transfers completes the reaction, giving an α-keto ester.

Interpretation Introduction

(a)

Interpretation:

How the given synthesis can be carried out is to be suggested.

Concept introduction:

β-Keto esters can be synthesized in a reaction known as Claisen condensation. The α-hydrogen in an carbonyl compound is relatively acidic because of the presence of an adjacent electron withdrawing group. A strong bulky, non-nuclophilic base extracts this proton, resulting in the formation of a carbon nucleophile. The nucleophile attacks and adds to the electrophilic carbon of a carbonyl compound such as an ester to form a tetrahedral intermediate. The elimination of the original alkoxide (acyl) group from this intermediate followed by proton transfers completes the reaction, giving an α-keto ester.

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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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 21, Problem 21.89P

Interpretation Introduction

(a)

Interpretation:

How the given synthesis can be carried out is to be suggested.

Concept introduction:

β-Keto esters can be synthesized in a reaction known as Claisen condensation. The α-hydrogen in an carbonyl compound is relatively acidic because of the presence of an adjacent electron withdrawing group. A strong bulky, non-nuclophilic base extracts this proton, resulting in the formation of a carbon nucleophile. The nucleophile attacks and adds to the electrophilic carbon of a carbonyl compound such as an ester to form a tetrahedral intermediate. The elimination of the original alkoxide (acyl) group from this intermediate followed by proton transfers completes the reaction, giving an α-keto ester.

Interpretation Introduction

(a)

Interpretation:

How the given synthesis can be carried out is to be suggested.

Concept introduction:

β-Keto esters can be synthesized in a reaction known as Claisen condensation. The α-hydrogen in an carbonyl compound is relatively acidic because of the presence of an adjacent electron withdrawing group. A strong bulky, non-nuclophilic base extracts this proton, resulting in the formation of a carbon nucleophile. The nucleophile attacks and adds to the electrophilic carbon of a carbonyl compound such as an ester to form a tetrahedral intermediate. The elimination of the original alkoxide (acyl) group from this intermediate followed by proton transfers completes the reaction, giving an α-keto ester.

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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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 21, Problem 21.89P

Interpretation Introduction

(a)

Interpretation:

How the given synthesis can be carried out is to be suggested.

Concept introduction:

β-Keto esters can be synthesized in a reaction known as Claisen condensation. The α-hydrogen in an carbonyl compound is relatively acidic because of the presence of an adjacent electron withdrawing group. A strong bulky, non-nuclophilic base extracts this proton, resulting in the formation of a carbon nucleophile. The nucleophile attacks and adds to the electrophilic carbon of a carbonyl compound such as an ester to form a tetrahedral intermediate. The elimination of the original alkoxide (acyl) group from this intermediate followed by proton transfers completes the reaction, giving an α-keto ester.

Interpretation Introduction

(a)

Interpretation:

How the given synthesis can be carried out is to be suggested.

Concept introduction:

β-Keto esters can be synthesized in a reaction known as Claisen condensation. The α-hydrogen in an carbonyl compound is relatively acidic because of the presence of an adjacent electron withdrawing group. A strong bulky, non-nuclophilic base extracts this proton, resulting in the formation of a carbon nucleophile. The nucleophile attacks and adds to the electrophilic carbon of a carbonyl compound such as an ester to form a tetrahedral intermediate. The elimination of the original alkoxide (acyl) group from this intermediate followed by proton transfers completes the reaction, giving an α-keto ester.

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Answer 5

Chapter 21, Problem 21.89P

Interpretation Introduction

(a)

Interpretation:

How the given synthesis can be carried out is to be suggested.

Concept introduction:

β-Keto esters can be synthesized in a reaction known as Claisen condensation. The α-hydrogen in an carbonyl compound is relatively acidic because of the presence of an adjacent electron withdrawing group. A strong bulky, non-nuclophilic base extracts this proton, resulting in the formation of a carbon nucleophile. The nucleophile attacks and adds to the electrophilic carbon of a carbonyl compound such as an ester to form a tetrahedral intermediate. The elimination of the original alkoxide (acyl) group from this intermediate followed by proton transfers completes the reaction, giving an α-keto ester.

Interpretation Introduction

(a)

Interpretation:

How the given synthesis can be carried out is to be suggested.

Concept introduction:

β-Keto esters can be synthesized in a reaction known as Claisen condensation. The α-hydrogen in an carbonyl compound is relatively acidic because of the presence of an adjacent electron withdrawing group. A strong bulky, non-nuclophilic base extracts this proton, resulting in the formation of a carbon nucleophile. The nucleophile attacks and adds to the electrophilic carbon of a carbonyl compound such as an ester to form a tetrahedral intermediate. The elimination of the original alkoxide (acyl) group from this intermediate followed by proton transfers completes the reaction, giving an α-keto ester.

Answer 6

Chapter 21, Problem 21.89P

Interpretation Introduction

(a)

Interpretation:

How the given synthesis can be carried out is to be suggested.

Concept introduction:

β-Keto esters can be synthesized in a reaction known as Claisen condensation. The α-hydrogen in an carbonyl compound is relatively acidic because of the presence of an adjacent electron withdrawing group. A strong bulky, non-nuclophilic base extracts this proton, resulting in the formation of a carbon nucleophile. The nucleophile attacks and adds to the electrophilic carbon of a carbonyl compound such as an ester to form a tetrahedral intermediate. The elimination of the original alkoxide (acyl) group from this intermediate followed by proton transfers completes the reaction, giving an α-keto ester.

Answer 7

Chapter 21, Problem 21.89P

Interpretation Introduction

(a)

Interpretation:

How the given synthesis can be carried out is to be suggested.

Concept introduction:

β-Keto esters can be synthesized in a reaction known as Claisen condensation. The α-hydrogen in an carbonyl compound is relatively acidic because of the presence of an adjacent electron withdrawing group. A strong bulky, non-nuclophilic base extracts this proton, resulting in the formation of a carbon nucleophile. The nucleophile attacks and adds to the electrophilic carbon of a carbonyl compound such as an ester to form a tetrahedral intermediate. The elimination of the original alkoxide (acyl) group from this intermediate followed by proton transfers completes the reaction, giving an α-keto ester.

Answer 8

Interpretation Introduction

(a)

Interpretation:

How the given synthesis can be carried out is to be suggested.

Concept introduction:

β-Keto esters can be synthesized in a reaction known as Claisen condensation. The α-hydrogen in an carbonyl compound is relatively acidic because of the presence of an adjacent electron withdrawing group. A strong bulky, non-nuclophilic base extracts this proton, resulting in the formation of a carbon nucleophile. The nucleophile attacks and adds to the electrophilic carbon of a carbonyl compound such as an ester to form a tetrahedral intermediate. The elimination of the original alkoxide (acyl) group from this intermediate followed by proton transfers completes the reaction, giving an α-keto ester.

Answer 9

Interpretation Introduction

(a)

Interpretation:

How the given synthesis can be carried out is to be suggested.

Concept introduction:

β-Keto esters can be synthesized in a reaction known as Claisen condensation. The α-hydrogen in an carbonyl compound is relatively acidic because of the presence of an adjacent electron withdrawing group. A strong bulky, non-nuclophilic base extracts this proton, resulting in the formation of a carbon nucleophile. The nucleophile attacks and adds to the electrophilic carbon of a carbonyl compound such as an ester to form a tetrahedral intermediate. The elimination of the original alkoxide (acyl) group from this intermediate followed by proton transfers completes the reaction, giving an α-keto ester.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 21 - Prob. 21.1P Ch. 21 - Prob. 21.2P Ch. 21 - Prob. 21.3P Ch. 21 - Prob. 21.4P Ch. 21 - Prob. 21.5P Ch. 21 - Prob. 21.6P Ch. 21 - Prob. 21.7P Ch. 21 - Prob. 21.8P Ch. 21 - Prob. 21.9P Ch. 21 - Prob. 21.10P

Solution Summary: The author explains how the -keto ester can be synthesized in a reaction known as Claisen condensation.

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