Book cover for Organic Chemistry

Organic Chemistry

John McMurry

ISBN #9781305080485

9th Edition

1,986 Questions

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21,829 Students Helped

Homework Questions

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Summary

Learning Objectives

Key Concepts

Example Problems

Explanations

Common Mistakes

Summary

Carboxylic acid derivatives encompass a broad array of compounds whose reactivity is governed largely by nucleophilic acyl substitution mechanisms. Understanding the structure, naming, and reactivity order of these derivatives (from highly reactive acid chlorides to less reactive amides) is crucial. Key reaction types include hydrolysis, alcoholysis (ester formation), aminolysis (amide formation), reduction, and Grignard reactions. Along with mechanism details, spectroscopic methods such as IR and NMR aid in identifying these compounds and confirming structural transformations in both laboratory and biochemical pathways.

Learning Objectives

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Key Concepts

CONCEPT

DEFINITION

Acid–Base Chemistry

The study of acids and bases using both the Brønsted–Lowry (proton-donating/accepting) and Lewis (electron pair accepting/donating) frameworks, including quantification via pKa values, which together explain chemical reactivity in organic molecules. •

Example Problems

Example 1

Give IUPAC names for the following substances: a. b. c. d. e. f. g. h. i.

Example 2

Draw structures corresponding to the following names: (a) Phenyl benzoate (b) $N$ -Ethyl- $N$ -methylbutanamide (c) 2,4 -Dimethylpentanoyl chloride (d) Methyl 1 -methylcyclohexanecarboxylate (e) Ethyl 3 -oxopentanoate (f) Methyl $p$ -bromobenzenethioate (g) Formic propanoic anhydride (h) $c i s-2$ -Methylcyclopentanecarbonyl bromide

Example 3

Show the mechanism of the following nucleophilic acyl substitution reaction, using curved arrows to indicate the electron flow in each step:

Example 4

Rank the compounds in each of the following sets in order of their expected reactivity toward nucleophilic acyl substitution: a. b.

Example 5

Predict the products of the following nucleophilic acyl substitution reactions: a. b. c. d.

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Step-by-Step Explanations

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Common Mistakes

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