Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 19, Problem 50P
Interpretation Introduction

Interpretation:

Synthesis of the given compound Darvon, starting with ethyl phenyl ketone is to be outlined.

Concept introduction:

Grignard reagent reactions with carbonyl groups are treated as acid–base reactions.

The reaction of Grignard reagents with carbonyl groups yields secondary and tertiary alcohols. These reactions are two-step reactions. In the first step, nucleophilic addition of carbonyl group takes place because Grignard reagent, being nucleophilic, uses its lone pair of electrons to form a bond with a carbon atom. This results in the formation of an alkoxide ion which remains associated with Mg2+ and X.

Organic Chemistry, Chapter 19, Problem 50P , additional homework tip  1

In the second step, addition of aqueous HX causes the protonation of the alkoxide ion, which leads to the formation of the alcohol and MgX2.

Organic Chemistry, Chapter 19, Problem 50P , additional homework tip  2

Mannich reaction: Carbonyl groups capable of forming enol react with primary or secondary amine and formaldehyde to form a β-amino carbonyl compounds known as Mannich base.

Alcohols react with acetic anhydride to form esters via nucleophilic substitution reaction.

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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 - Prob. 50PCh. 19 - Prob. 51PCh. 19 - Prob. 52PCh. 19 - Prob. 53PCh. 19 - The Perkin condensation is an aldol-type...Ch. 19 - 19.55 (a) Infrared spectroscopy provides an easy...Ch. 19 - Allowing acetone to react with 2 molar equivalents...Ch. 19 - (+) Fenchone is a terpenoid that can be isolated...Ch. 19 - Prob. 58PCh. 19 - Prob. 59PCh. 19 - 19.60 Develop a synthesis for the following...Ch. 19 - 19.61 Provide a mechanism for each of the...Ch. 19 - 19.62 (a) Deduce the structure of product A,...Ch. 19 - Prob. 63PCh. 19 - Prob. 1LGP
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