Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Textbook Question
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Chapter 19, Problem 1PP

PRACTICE PROBLEM 19.1

(a) Write a mechanism. for all steps of the Claisen condensation that take place when ethyl propanoate reacts with ethoxide ion.

(b) What products form when the reaction mixture is acidified?

Expert Solution & Answer
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Interpretation Introduction

Interpretation: The mechanism for all the steps of Claisen condensation when ethyl propanate reacts with ethoxide ion is to be written and when the reaction mixture acidified the product of the reaction is to be determined.

Concept introduction:

The Claisen condensation is the carbon-carbon bond forming reaction and important for the preparing βKeto ester.

In Claisen condensation ester of one molecule adds to the carbonyl carbon of the another molecule and formation of βKeto ester takes place.

Answer to Problem 1PP

Solution:

(a)

Organic Chemistry, Chapter 19, Problem 1PP , additional homework tip  1

Organic Chemistry, Chapter 19, Problem 1PP , additional homework tip  2

Organic Chemistry, Chapter 19, Problem 1PP , additional homework tip  3

(b)

Organic Chemistry, Chapter 19, Problem 1PP , additional homework tip  4

Organic Chemistry, Chapter 19, Problem 1PP , additional homework tip  5

Explanation of Solution

The mechanism for the reaction between ethylproponate and ethoxide ion is as follows:

Step 1

Organic Chemistry, Chapter 19, Problem 1PP , additional homework tip  6

Step 2

Organic Chemistry, Chapter 19, Problem 1PP , additional homework tip  7

Step 3

Organic Chemistry, Chapter 19, Problem 1PP , additional homework tip  8

(b)

When the reaction mixture is acidified the reaction takes place is as follows;

Organic Chemistry, Chapter 19, Problem 1PP , additional homework tip  9

Hence, the product formed when the reaction mixture acidified is as follows;

Organic Chemistry, Chapter 19, Problem 1PP , additional homework tip  10

Organic Chemistry, Chapter 19, Problem 1PP , additional homework tip  11

Organic Chemistry, Chapter 19, Problem 1PP , additional homework tip  12

Organic Chemistry, Chapter 19, Problem 1PP , additional homework tip  13

Organic Chemistry, Chapter 19, Problem 1PP , additional homework tip  14

Organic Chemistry, Chapter 19, Problem 1PP , additional homework tip  15

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Chapter 19 Solutions

Organic Chemistry

Ch. 19 - Practice Problem 19.11 Outlined below is a...Ch. 19 - Prob. 12PPCh. 19 - Prob. 13PPCh. 19 - Prob. 14PPCh. 19 - Practice Problem 19.15 Starting with ketones and...Ch. 19 - Practice Problem 19.16 Assuming that dehydration...Ch. 19 - Practice Problem 19.17 What starting compound...Ch. 19 - Practice Problem 19.18 What experimental...Ch. 19 - Prob. 19PPCh. 19 - Practice Problem 19.20 When acrolein (propenal)...Ch. 19 - Prob. 21PPCh. 19 - PRACTICE PROBLEM 19.22 Qutline reasonable...Ch. 19 - Prob. 23PCh. 19 - Show all steps in the following syntheses. You may...Ch. 19 - Prob. 25PCh. 19 - Prob. 26PCh. 19 - Prob. 27PCh. 19 - 19.28 Show how the diketone at the right could be...Ch. 19 - Prob. 29PCh. 19 - 19.30 Write a detailed mechanism for the following...Ch. 19 - Prob. 31PCh. 19 - Prob. 32PCh. 19 - 19.33 Predict the products from each of the...Ch. 19 - Prob. 34PCh. 19 - Show how each of the following transformations...Ch. 19 - Prob. 36PCh. 19 - What reagents would you use to bring about each...Ch. 19 - Prob. 38PCh. 19 - Prob. 39PCh. 19 - 19.40 When the aldol reaction of acetaldehyde is...Ch. 19 - Prob. 41PCh. 19 - Prob. 42PCh. 19 - 19.43 The following reaction illustrates the...Ch. 19 - What is the structure of the cyclic compound that...Ch. 19 - Prob. 45PCh. 19 - Prob. 46PCh. 19 - Prob. 47PCh. 19 - Predict the products from the following reactions....Ch. 19 - Prob. 49PCh. 19 - 19.50 (+)-Fenchone is a terpenoid that can be...Ch. 19 - Prob. 51PCh. 19 - Prob. 52PCh. 19 - Prob. 53PCh. 19 - Prob. 54PCh. 19 - The Perkin condensation is an aldol-type...Ch. 19 - 19.55 (a) Infrared spectroscopy provides an easy...Ch. 19 - Prob. 57PCh. 19 - 19.61 Provide a mechanism for each of the...Ch. 19 - 19.62 (a) Deduce the structure of product A,...Ch. 19 - 19.60 Write the structures of the three products...Ch. 19 - Prob. 1LGPCh. 19 - Which hydrogen atoms in the following ester are...Ch. 19 - Prob. 2QCh. 19 - 19.3 What starting materials could be used in a...Ch. 19 - Supply the missing reagents, intermediates, and...Ch. 19 - Prob. 5QCh. 19 - Prob. 6QCh. 19 - Prob. 7QCh. 19 - Prob. 8Q
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