(a) Interpretation: The complete, detailed mechanism for the given reaction and the major product are to be drawn. Concept introduction: In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester. If the base, in a Claisen condensation, is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

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Answer 1

Question

Chapter 21, Problem 21.62P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base, in a Claisen condensation, is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce a β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

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Done 11:14 ⚫ worksheets.beyondlabz.com 5 (a). Using the peak information you listed in the tables for both structures, assign each peak to that portion of the structure that produces the peak in the NMR spectrum. Draw this diagram on your own sheet of paper and attach the sketch of your drawing to this question. Question 6 5 (b). Using the peak information you listed in the tables for both structures, assign each peak to that portion of the structure that produces the peak in the NMR spectrum. Draw this diagram on your own sheet of paper and attach the sketch of your drawing to this question. Question 7 6. Are there any differences between the spectra you obtained in Beyond Labz and the predicted spectra? If so, what were the differences? <

2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled** Peak Chemical Shift (d) 5.7 1 Multiplicity multiplate .......... 5.04 double of doublet 2 4.98 double of doublet 3 4.05 doublet of quartet 4 5 LO 3.80 quartet 1.3 doublet 6 Peak Chemical Shift (d) Multiplicity

Interpreting NMR spectra is a skill that often requires some amount of practice, which, in turn, necessitates access to a collection of NMR spectra. Beyond Labz Organic Synthesis and Organic Qualitative Analysis have spectral libraries containing over 700 1H NMR spectra. In this assignment, you will take advantage of this by first predicting the NMR spectra for two closely related compounds and then checking your predictions by looking up the actual spectra in the spectra library. After completing this assignment, you may wish to select other compounds for additional practice. 1. Write the IUPAC names for the following two structures: Question 2 Question 3 2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled**

Answer 2

Question

Chapter 21, Problem 21.62P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base, in a Claisen condensation, is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce a β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

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Answer 3

Question

Chapter 21, Problem 21.62P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base, in a Claisen condensation, is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce a β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

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Answer 4

Question

Chapter 21, Problem 21.62P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base, in a Claisen condensation, is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce a β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

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Answer 5

Chapter 21, Problem 21.62P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base, in a Claisen condensation, is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce a β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Answer 6

Chapter 21, Problem 21.62P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base, in a Claisen condensation, is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

Answer 7

Chapter 21, Problem 21.62P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base, in a Claisen condensation, is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce a β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce a β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Answer 12

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Answer 13

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Answer 14

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Answer 15

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 illustrates the complete, detailed mechanism for the given reaction and the major product using the reactants given on the basis of Claisen condensation reaction mechanism.

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