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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.SE, Problem 68AP
Textbook Problem
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When a carboxylic acid is dissolved in isotopically labeled water, the label rapidly becomes incorporated into both oxygen atoms of the carboxylic acid. Explain.

Chapter 21.SE, Problem 68AP, When a carboxylic acid is dissolved in isotopically labeled water, the label rapidly becomes

Interpretation Introduction

Interpretation:

Of the four aldehyde structures that fits best with the IR spectrum given is to be chosen.

Concept introduction:

Aldehydes and ketones show a strong absorption band in IR from 1660-1770 cm-1. Aldehydes show two characteristic C-H absorptions between 2700-2760 cm-1 and 2800-2860 cm-1. Saturated aldehydes absorb near 1730 cm-1 while aromatic aldehydes and α, β- unsaturated aldehydes absorb near 1705 cm-1.

To choose:

The structure, out of the four given, which fits best with the IR spectrum given.

Explanation of Solution

Structures (a) and (c) represent those of α, β- unsaturated ketones which will show an IR absorption at 1705 cm-1. The compound has the carbonyl absorption at 1727 cm-1. So these two structures do not represent the compound...

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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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