ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
Question
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Chapter 23, Problem 23.15P
Interpretation Introduction

(a)

Interpretation: The product that is formed by the reaction of the given compound with LDA in the presence of THF solution at low temperature, followed by CH3CH2I is to be identified.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The nucleophilic reaction that consists of bimolecular as well as bond-making and bond-breaking steps is termed as SN2 reactions. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

The bulky base like LDA always abstracts the proton from the side of less substituted Catom.

Expert Solution
Check Mark

Answer to Problem 23.15P

The product that is formed by the reaction of the given compound with LDA in the presence of THF solution at low temperature, followed by CH3CH2I is shown below.

ORGANIC CHEMISTRY, Chapter 23, Problem 23.15P , additional homework tip  1

Explanation of Solution

The product that is formed by the reaction of the given compound with LDA in the presence of THF solution at low temperature, followed by CH3CH2I is shown is shown as,

ORGANIC CHEMISTRY, Chapter 23, Problem 23.15P , additional homework tip  2

Figure 1

In this reaction, the given compound is treated with LDA in the presence of THF solution to form an enolate ion. The strong base, LDA abstracts a proton from the less substituted carbon atom of the compound. Then methyl iodide reacts with the enolte ion to form the desired product.

Conclusion

The product that is formed by the reaction of the given compound with LDA in the presence of THF solution at low temperature, followed by CH3CH2I is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The product that is formed by the reaction of the given compound with LDA in the presence of THF solution at low temperature, followed by CH3CH2I is to be identified.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The nucleophilic reaction that consists of bimolecular as well as bond-making and bond-breaking steps is termed as SN2 reactions. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

The bulky base like LDA always abstracts the proton from the side of less substituted Catom.

Expert Solution
Check Mark

Answer to Problem 23.15P

The product that is formed by the reaction of the given compound with LDA in the presence of THF solution at low temperature, followed by CH3CH2I is shown below.

ORGANIC CHEMISTRY, Chapter 23, Problem 23.15P , additional homework tip  3

Explanation of Solution

The product that is formed by the reaction of the given compound with LDA in the presence of THF solution at low temperature, followed by CH3CH2I is shown is shown as,

ORGANIC CHEMISTRY, Chapter 23, Problem 23.15P , additional homework tip  4

Figure 2

In this reaction, the given compound is treated with LDA in the presence of THF solution to form an enolate ion. The strong base, LDA abstracts a proton from the less substituted carbon atom or αcarbon atom of the compound. Then methyl iodide reacts with the enolte ion to form the desired product.

Conclusion

The product that is formed by the reaction of the given compound with LDA in the presence of THF solution at low temperature, followed by CH3CH2I is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation: The product that is formed by the reaction of the given compound with LDA in the presence of THF solution at low temperature, followed by CH3CH2I is to be identified.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The nucleophilic reaction that consists of bimolecular as well as bond-making and bond-breaking steps is termed as SN2 reactions. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

The bulky base like LDA always abstracts the proton from the side of less substituted Catom.

Expert Solution
Check Mark

Answer to Problem 23.15P

The product that is formed by the reaction of the given compound with LDA in the presence of THF solution at low temperature, followed by CH3CH2I is shown below.

ORGANIC CHEMISTRY, Chapter 23, Problem 23.15P , additional homework tip  5

Explanation of Solution

The product that is formed by the reaction of the given compound with LDA in the presence of THF solution at low temperature, followed by CH3CH2I is shown is shown as,

ORGANIC CHEMISTRY, Chapter 23, Problem 23.15P , additional homework tip  6

Figure 3

In this reaction, the given compound is treated with LDA in the presence of THF solution to form an enolate ion. The strong base, LDA abstracts a proton from the less substituted carbon atom or αcarbon atom of the compound. Then methyl iodide reacts with the enolte ion to form the desired product.

Conclusion

The product that is formed by the reaction of the given compound with LDA in the presence of THF solution at low temperature, followed by CH3CH2I is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: The product that is formed by the reaction of the given compound with LDA in the presence of THF solution at low temperature, followed by CH3CH2I is to be identified.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The nucleophilic reaction that consists of bimolecular as well as bond-making and bond-breaking steps is termed as SN2 reactions. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

The bulky base like LDA always abstracts the proton from the side of less substituted Catom.

Expert Solution
Check Mark

Answer to Problem 23.15P

The product that is formed by the reaction of the given compound with LDA in the presence of THF solution at low temperature, followed by CH3CH2I is,

ORGANIC CHEMISTRY, Chapter 23, Problem 23.15P , additional homework tip  7

Explanation of Solution

The product that is formed by the reaction of the given compound with LDA in the presence of THF solution at low temperature, followed by CH3CH2I is shown is shown as,

ORGANIC CHEMISTRY, Chapter 23, Problem 23.15P , additional homework tip  8

Figure 4

In this reaction, the given compound is treated with LDA in the presence of THF solution to form an enolate ion. The strong base, LDA abstracts a proton from the less substituted carbon atom or αcarbon atom of the compound. Then methyl iodide reacts with the enolte ion to form the desired product.

Conclusion

The product that is formed by the reaction of the given compound with LDA in the presence of THF solution at low temperature, followed by CH3CH2I is shown in Figure 4.

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Chapter 23 Solutions

ORGANIC CHEMISTRY

Ch. 23 - Problem 23.11 Draw the products of each...Ch. 23 - Problem 23.12 Draw the products of each reaction....Ch. 23 - Prob. 23.13PCh. 23 - Prob. 23.14PCh. 23 - Prob. 23.15PCh. 23 - Prob. 23.16PCh. 23 - Prob. 23.17PCh. 23 - Problem 23.18 How can pentan-2-one be converted...Ch. 23 - Problem 23.19 Identify A, B, and C, intermediates...Ch. 23 - Problem 23.20 Which of the following compounds...Ch. 23 - Problem 23.21 Draw the products of each...Ch. 23 - Prob. 23.22PCh. 23 - Prob. 23.23PCh. 23 - Prob. 23.24PCh. 23 - Prob. 23.25PCh. 23 - Prob. 23.26PCh. 23 - Prob. 23.27PCh. 23 - Prob. 23.28PCh. 23 - 23.29 Draw enol tautomer(s) for each compound....Ch. 23 - 22.30 The cis ketone A is isomerized to a trans...Ch. 23 - 23.31 Draw enol tautomer(s) for each compound. ...Ch. 23 - Prob. 23.32PCh. 23 - Prob. 23.33PCh. 23 - Prob. 23.34PCh. 23 - 23.35 Rank the labeled protons in each compound in...Ch. 23 - Prob. 23.36PCh. 23 - Prob. 23.37PCh. 23 - 23.38 Acyclovir is an effective antiviral agent...Ch. 23 - 23.39 Explain why forms two different alkylation...Ch. 23 - Prob. 23.40PCh. 23 - 23.41 Acid-catalyzed bromination of pentanone ...Ch. 23 - 23.42 Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.43PCh. 23 - Prob. 23.44PCh. 23 - 23.45 Devise a synthesis of valproic acid , a...Ch. 23 - 23.46 Synthesize each compound from diethyl...Ch. 23 - Prob. 23.47PCh. 23 - Prob. 23.48PCh. 23 - Prob. 23.49PCh. 23 - 23.50 Draw the organic products formed in each...Ch. 23 - 23.51 Draw the products formed (including...Ch. 23 - Prob. 23.52PCh. 23 - Prob. 23.53PCh. 23 - 23.54 Clopidogrel is the generic name for Plavix,...Ch. 23 - 23.55 What reaction conditions—base, solvent, and...Ch. 23 - Prob. 23.56PCh. 23 - 23.57 Draw a stepwise mechanism showing how two...Ch. 23 - 23.58 Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.59PCh. 23 - 23.60 Draw stepwise mechanisms illustrating how...Ch. 23 - Prob. 23.61PCh. 23 - Prob. 23.62PCh. 23 - 23.63 Synthesize each compound from cyclohexanone...Ch. 23 - Prob. 23.64PCh. 23 - Prob. 23.65PCh. 23 - 23.66 Synthesize (Z)-hept-5-en-2-one from ethyl...Ch. 23 - Prob. 23.67PCh. 23 - 23.68 Capsaicin, the spicy component of hot...Ch. 23 - 23.69 Treatment of W with , followed by , affords...Ch. 23 - Prob. 23.70PCh. 23 - Prob. 23.71PCh. 23 - Prob. 23.72PCh. 23 - Prob. 23.73PCh. 23 - Prob. 23.74P
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