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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13,325 Students Helped

Homework Questions

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Summary

Learning Objectives

Key Concepts

Example Problems

Explanations

Common Mistakes

Summary

This chapter section outlines the rich chemistry of oxygen- and sulfur-containing functional groups including alcohols, phenols, thiols, ethers, and sulfides. Key synthetic routes for preparing alcohols from carbonyl compounds (via reduction or Grignard addition) are described, along with diverse reactions such as dehydration, oxidation, and nucleophilic substitutions. Additionally, the discussion covers protecting groups like TMS ethers, rearrangement reactions such as the Claisen rearrangement, and the importance of spectroscopic techniques in structure elucidation. Crown ethers and ionophores also illustrate how complexation affects solubility and reactivity. Overall, the content emphasizes reaction mechanisms, selectivity, and practical applications in synthetic organic and biological chemistry.

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-Ethylbut-2-en-1-ol (b) Cyclohex-3-en-1-ol (c) trans-3-Chlorocycloheptanol (d) Pentane-1,4-dithiol (e) 2,4-Dimethylphenol (f) o-(2-Hydroxyethyl)phenol

Example 3

Rank the following substances in order of increasing acidity: (a) Phenol, $p$ -methylphenol, $p$ -(trifluoromethyl)phenol (b) Benzyl alcohol, phenol, $p$ -hydroxybenzoic acid

Example 4

$p$ -Nitrobenzyl alcohol is more acidic than benzyl alcohol, but $p$ -methoxybenzyl alcohol is less acidic. Explain.

Example 5

Which would you expect to be more acidic, methanethiol or thiophenol, $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{SH}$ ? Explain.

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Step-by-Step Explanations

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Common Mistakes

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