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Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485

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BuyFindarrow_forward

Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485
Chapter 21.4, Problem 12P
Textbook Problem
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How could you prepare the following amides using an acid chloride and an amine or ammonia?

(a) CH3CH2CONHCH3

(b) N,N-Diethylbenzamide

(c) Propanamide

Interpretation Introduction

a) CH3CH2CONHCH3

Interpretation:

To prepare the given amides by using an acid chloride and an amine or ammonia.

Concept introduction:

Evidently, in deciding the starting materials (reagents) for the synthesis, we observe that there are two distinct parts of the amide viz the acyl part Organic Chemistry, Chapter 21.4, Problem 12P , additional homework tip  1 which should come from the respective acyl chloride viz propanoyl chloride; and the amine part Organic Chemistry, Chapter 21.4, Problem 12P , additional homework tip  2, which should come from the oppropriate amine methylamine.

Explanation of Solution

Target amide given is

In the present example, the reaction should thus be

Essentially, the reaction is a nucleophilic acyl substitution; the pyridine being added to stabilise the Hcl formed...

Interpretation Introduction

b) N,N-Diethylbenzamide

Interpretation:

To prepare the given amides by using an acid chloride and an amine or ammonia.

Concept introduction:

Evidently, introspection of the target molecule viz the amide, shows that it has two distinct parts, viz the acyl part, Phco should come from the acid chloride, viz benzoyl chloride, and the amine part should come from the appropriate amine, in this case it is N,N-diethyl amine.

Interpretation Introduction

c) Propanamide

Interpretation:

To prepare the given amides by using an acid chloride and an amine or ammonia.

Concept introduction:

Introspection of the target amide shows that there are two distinct parts viz, the acyl part and the amine part the acyl part should come from the appropriate acid chloride in this case, it is propanoyl chloride while the amine part should be provided from ammonia.

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Chapter 21 Solutions

Organic Chemistry
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Ch. 21.4 - Write the mechanism of the reaction just shown...Ch. 21.4 - How could you prepare the following amides using...Ch. 21.4 - How could you prepare the following ketones by...Ch. 21.5 - Write the mechanism of the reaction between...Ch. 21.5 - What product would you expect from reaction of one...Ch. 21.6 - Why is the saponification of an ester...Ch. 21.6 - What product would you expect from the reaction of...Ch. 21.6 - Show the products you would obtain by reduction of...Ch. 21.6 - What ester and what Grignard reagent might you...Ch. 21.7 - How would you convert N-ethylbenzamide to each of...Ch. 21.7 - How would you use the reaction of an amide with...Ch. 21.8 - Write the mechanism of the reaction shown in...Ch. 21.9 - Draw structures of the step-growth polymers you...Ch. 21.9 - Kevlar, a nylon polymer prepared by reaction of...Ch. 21.SE - Name the following compounds:Ch. 21.SE - How would you prepare the following compounds...Ch. 21.SE - The following structure represents a tetrahedral...Ch. 21.SE - Electrostatic potential maps of a typical amide...Ch. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the complete...Ch. 21.SE - Pivalic mixed anhydrides are often used to form...Ch. 21.SE - When 4-dimethylaminopyridine (DMAP) is added in...Ch. 21.SE - Fats are biosynthesized from glycerol 3-phosphate...Ch. 21.SE - Treatment of an -amino acid with DCC yields a...Ch. 21.SE - Succinic anhydride yields the cyclic imide...Ch. 21.SE - The hydrolysis of a biological thioester to the...Ch. 21.SE - One step in the gluconeogenesis pathway for the...Ch. 21.SE - Bacteria typically develop a resistance to...Ch. 21.SE - The following reaction, called the benzilic acid...Ch. 21.SE - In the iodoform reaction, a triiodomethyl ketone...Ch. 21.SE - Give IUPAC names for the following compounds:Ch. 21.SE - Draw structures corresponding to the following...Ch. 21.SE - Draw and name compounds that meet the following...Ch. 21.SE - Predict the product, if any, of reaction between...Ch. 21.SE - Answer Problem 21-48 for reaction of the listed...Ch. 21.SE - Answer Problem 21-48 for reaction of the listed...Ch. 21.SE - What product would you expect to obtain from...Ch. 21.SE - How might you prepare the following compounds from...Ch. 21.SE - Predict the product(s) of the following reactions:Ch. 21.SE - The following reactivity order has been found for...Ch. 21.SE - Explain the observation that attempted Fischer...Ch. 21.SE - Outline methods for the preparation of...Ch. 21.SE - Treatment of 5-aminopentanoic acid with DCC...Ch. 21.SE - When ethyl benzoate is heated in methanol...Ch. 21.SE - tert-Butoxycarbonyl azide, a reagent used in...Ch. 21.SE - The step-growth polymer nylon 6 is prepared from...Ch. 21.SE - Qiana, a polyamide fiber with a silky texture, has...Ch. 21.SE - What is the structure of the polymer produced by...Ch. 21.SE - Polyimides with the structure shown are used as...Ch. 21.SE - How would you distinguish spectroscopically...Ch. 21.SE - Propose a structure for a compound, C4H7ClO2, that...Ch. 21.SE - Assign structures to compounds with the following...Ch. 21.SE - The following reactivity order has been found for...Ch. 21.SE - When a carboxylic acid is dissolved in...Ch. 21.SE - We said in Section 21-6 that mechanistic studies...Ch. 21.SE - Treatment of a carboxylic acid with...Ch. 21.SE - Butacetin is an analgesic (pain-killing) agent...Ch. 21.SE - Phenyl 4-aminosalicylate is a drug used in the...Ch. 21.SE - N,N-Diethyl-m-toluamide (DEET) is the active...Ch. 21.SE - Tranexamic acid, a drug useful against blood...Ch. 21.SE - One frequently used method for preparing methyl...Ch. 21.SE - Draw the structure of the polymer you would expect...Ch. 21.SE - Assign structures to compounds with the following...Ch. 21.SE - Propose structures for compounds with the...Ch. 21.SE - Propose a structure for the compound with the...Ch. 21.SE - Draw the structure of the compound that produced...Ch. 21.SE - When an amide is formed from an acid chloride or...Ch. 21.SE - Epoxy adhesives are prepared in two steps. SN2...

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