Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
Question
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Chapter 23, Problem 23.7P
Interpretation Introduction

(a)

Interpretation: The product that is formed by the reaction of the given starting material with LDA in the presence of THF solution at 78°C is to be drawn.

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.

Interpretation Introduction

(b)

Interpretation: The product that is formed by the reaction of the given starting material with LDA in the presence of THF solution at 78°C is to be drawn.

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.

Interpretation Introduction

(c)

Interpretation: The product that is formed by the reaction of the given starting material with LDA in the presence of THF solution at 78°C is to be drawn.

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.

Interpretation Introduction

(d)

Interpretation: The product that is formed by the reaction of the given starting material with LDA in the presence of THF solution at 78°C is to be drawn.

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.

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Chapter 23 Solutions

Organic Chemistry

Ch. 23 - Prob. 23.11PCh. 23 - Problem 23.11 Draw the products of each...Ch. 23 - Problem 23.12 Draw the products of each reaction....Ch. 23 - Prob. 23.14PCh. 23 - Prob. 23.15PCh. 23 - Prob. 23.16PCh. 23 - Prob. 23.17PCh. 23 - Prob. 23.18PCh. 23 - Problem 23.18 How can pentan-2-one be converted...Ch. 23 - Problem 23.19 Identify A, B, and C, intermediates...Ch. 23 - Prob. 23.21PCh. 23 - Problem 23.21 Draw the products of each...Ch. 23 - Prob. 23.23PCh. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Prob. 23.25PCh. 23 - Prob. 23.26PCh. 23 - Prob. 23.27PCh. 23 - Prob. 23.28PCh. 23 - Prob. 23.29PCh. 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 - Draw enol tautomers for each compound. a. b. c.Ch. 23 - Prob. 23.33PCh. 23 - What hydrogen atoms in each compound have a pKa25?...Ch. 23 - Rank the labeled protons in each compound in order...Ch. 23 - Prob. 23.36PCh. 23 - Prob. 23.37PCh. 23 - Prob. 23.38PCh. 23 - Prob. 23.39PCh. 23 - 23.38 Acyclovir is an effective antiviral agent...Ch. 23 - Prob. 23.41PCh. 23 - 23.39 Explain why forms two different alkylation...Ch. 23 - 23.41 Acid-catalyzed bromination of pentanone ...Ch. 23 - Draw a stepwise mechanism for each reaction. a. b.Ch. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Use the malonic ester synthesis to prepare each...Ch. 23 - 23.45 Devise a synthesis of valproic acid , a...Ch. 23 - Synthesize each compound from diethyl malonate....Ch. 23 - Prob. 23.49PCh. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Synthesize each compound from ethyl acetoacetate....Ch. 23 - Draw the organic products formed in each reaction....Ch. 23 - 23.51 Draw the products formed (including...Ch. 23 - Prob. 23.54PCh. 23 - 23.54 Clopidogrel is the generic name for Plavix,...Ch. 23 - 23.55 What reaction conditions—base, solvent, and...Ch. 23 - Explain why each of the following reactions will...Ch. 23 - Prob. 23.58PCh. 23 - 23.57 Draw a stepwise mechanism showing how two...Ch. 23 - 23.58 Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.61PCh. 23 - 23.60 Draw stepwise mechanisms illustrating how...Ch. 23 - Prob. 23.63PCh. 23 - Prob. 23.64PCh. 23 - Convert acetophenone (C6H5COCH3) into each of the...Ch. 23 - Prob. 23.66PCh. 23 - Prob. 23.67PCh. 23 - Prob. 23.68PCh. 23 - Synthesize each product from ethyl acetoacetate...Ch. 23 - Prob. 23.70PCh. 23 - Prob. 23.71PCh. 23 - 23.68 Capsaicin, the spicy component of hot...Ch. 23 - 23.69 Treatment of W with , followed by , affords...Ch. 23 - Prob. 23.74PCh. 23 - Prob. 23.75PCh. 23 - Prob. 23.76PCh. 23 - Prob. 23.77PCh. 23 - Prob. 23.78P
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