Book cover for Organic chemistry with biological applications

Organic chemistry with biological applications

John E. McMurry

ISBN #9781285842912

3rd Edition

1,528 Questions

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Homework Questions

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Summary

Learning Objectives

Key Concepts

Example Problems

Explanations

Common Mistakes

Summary

This section covers the structural features, nomenclature, and reactivity of carboxylic acids and nitriles. It emphasizes the importance of resonance stabilization in carboxylate ions, which leads to higher acidity than seen in simple alcohols, and explains how substituent effects influence acid strength. Detailed reaction mechanisms including oxidation, hydrolysis, and nucleophilic acyl substitution are discussed, along with applications in both synthetic organic chemistry and biochemical pathways. Spectroscopic techniques (IR and NMR) provide clear signatures to identify these functional groups and their derivatives.

Learning Objectives

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Key Concepts

CONCEPT

DEFINITION

Definition: The study of molecular reactivity via polar covalent bonds where differences in electronegativity create dipole moments, guiding acid–base behavior.

The study of molecular reactivity via polar covalent bonds where differences in electronegativity create dipole moments, guiding acid–base behavior. •

Example Problems

Example 1

Give IUPAC names for the following compounds:

Example 2

Draw structures corresponding to the following IUPAC names: (a) 2,3-Dimethylhexanoic acid (b) 4 -Methylpentanoic acid (c) trans-Cyclobutane-1,2-dicarboxylic acid (d) $o$ -Hydroxybenzoic acid (e) $(9 Z, 12 Z)$ -Octadeca-9,12-dienoic acid (f) Pent-2-enenitrile

Example 3

Assume you have a mixture of naphthalene and benzoic acid that you want to separate. How might you take advantage of the acidity of one component in the mixture to effect a separation?

Example 4

The $K_{\mathrm{a}}$ for dichloroacetic acid is $3.32 \times 10^{-2} .$ Approximately what percentage of the acid is dissociated in a $0.10 \mathrm{M}$ aqueous solution?

Example 5

Calculate the percentages of dissociated and undissociated forms present in the following solutions: (a) $0.0010 \mathrm{M}$ glycolic acid $\left(\mathrm{HOCH}_{2} \mathrm{CO}_{2} \mathrm{H} ; \mathrm{p} K_{\mathrm{a}}=3.83\right)$ at $\mathrm{pH}=4.50$ (b) $0.0020 \mathrm{M}$ propanoic acid $\left(\mathrm{p} K_{\mathrm{a}}=4.87\right)$ at $\mathrm{pH}=5.30$

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Step-by-Step Explanations

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Common Mistakes

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