Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
Question
Book Icon
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.

Blurred answer
Students have asked these similar questions
Indicate the correct option.a) Graphite conducts electricity, being an isotropic materialb) Graphite is not a conductor of electricityc) Both are false
(f) SO: Best Lewis Structure 3 e group geometry:_ shape/molecular geometry:, (g) CF2CF2 Best Lewis Structure polarity: e group arrangement:_ shape/molecular geometry: (h) (NH4)2SO4 Best Lewis Structure polarity: e group arrangement: shape/molecular geometry: polarity: Sketch (with angles): Sketch (with angles): Sketch (with angles):
1. Problem Set 3b Chem 141 For each of the following compounds draw the BEST Lewis Structure then sketch the molecule (showing bond angles). Identify (i) electron group geometry (ii) shape around EACH central atom (iii) whether the molecule is polar or non-polar (iv) (a) SeF4 Best Lewis Structure e group arrangement:_ shape/molecular geometry: polarity: (b) AsOBr3 Best Lewis Structure e group arrangement:_ shape/molecular geometry: polarity: Sketch (with angles): Sketch (with angles):

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
Knowledge Booster
Background pattern image
Recommended textbooks for you
  • Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning