Book cover for Organic Chemistry

Organic Chemistry

John McMurry

ISBN #9781305080485

9th Edition

1,986 Questions

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Summary

Learning Objectives

Key Concepts

Example Problems

Explanations

Common Mistakes

Summary

Chapter 7 on Alkenes: Structure and Reactivity covers the industrial production and applications of alkenes, methods for calculating the degree of unsaturation, systematic IUPAC nomenclature, and the assignment of stereochemistry through cis–trans and E/Z designations. It further explains the electrophilic addition mechanism, emphasizing the formation and rearrangement of carbocation intermediates, and integrates principles like hyperconjugation and the Hammond postulate to explain alkene stability and reaction kinetics.

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

Calculate the degree of unsaturation in each of the following formulas, and then draw as many structures as you can for each: (a) $\mathrm{C}_{4} \mathrm{H}_{8}$ (b) $\mathrm{C}_{4} \mathrm{H}_{6}$ (c) $\mathrm{C}_{3} \mathrm{H}_{4}$

Example 2

Calculate the degree of unsaturation in each of the following formulas: (a) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{~N}$ (b) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NO}_{2}$ (c) $\mathrm{C}_{8} \mathrm{H}_{9} \mathrm{Cl}_{3}$ (d) $\mathrm{C}_{9} \mathrm{H}_{16} \mathrm{Br}_{2}$ (e) $\mathrm{C}_{10} \mathrm{H}_{12} \mathrm{~N}_{2} \mathrm{O}_{3}$ (f) $\mathrm{C}_{20} \mathrm{H}_{32} \mathrm{ClN}$

Example 3

Diazepam, marketed as an antianxiety medication under the name Valium, has three rings, eight double bonds, and the formula $\mathrm{C}_{16} \mathrm{H}_{?} \mathrm{ClN}_{2} \mathrm{O} .$ How many hydrogens does diazepam have? (Calculate the answer; don't count hydrogens in the structure.)

Example 4

Give IUPAC names for the following compounds:

Example 5

Draw structures corresponding to the following IUPAC names: (a) 2 -Methyl-1,5-hexadiene (b) 3 -Ethyl-2,2-dimethyl-3-heptene (c) 2,3,3 -Trimethyl-1,4,6-octatriene (d) 3,4 -Diisopropyl-2,5-dimethyl-3-hexene

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Step-by-Step Explanations

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Common Mistakes

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