Book cover for Organic Chemistry

Organic Chemistry

John McMurry

ISBN #9781305080485

9th Edition

1,986 Questions

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Homework Questions

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Summary

Learning Objectives

Key Concepts

Example Problems

Explanations

Common Mistakes

Summary

This chapter provides an in-depth exploration of synthetic polymers and their production mechanisms. Key topics include chain-growth and step-growth polymerizations, which define how monomers connect, as well as the role of catalysts like Ziegler–Natta in controlling stereochemistry. The material further highlights the diversity of polymer types—ranging from thermoplastics to thermosetting resins—and illustrates how polymer structure, such as crystallinity and cross-linking, significantly affects physical properties and applications. Emerging techniques such as olefin metathesis and the development of biodegradable polymers point to future innovations in material science.

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

Order the following monomers with respect to their expected reactivity toward cationic polymerization, and explain your answer: $\mathrm{H}_{2} \mathrm{C}=\mathrm{CHCH}_{3}, \mathrm{H}_{2} \mathrm{C}=\mathrm{CHCl}, \mathrm{H}_{2} \mathrm{C}=\mathrm{CH}-\mathrm{C}_{6} \mathrm{H}_{5}, \mathrm{H}_{2} \mathrm{C}=\mathrm{CHCO}_{2} \mathrm{CH}_{3}$

Example 2

Order the following monomers with respect to their expected reactivity toward anionic polymerization, and explain your answer: $\mathrm{H}_{2} \mathrm{C}=\mathrm{CHCH}_{3}, \mathrm{H}_{2} \mathrm{C}=\mathrm{CHC} \equiv \mathrm{N}, \mathrm{H}_{2} \mathrm{C}=\mathrm{CHC}_{6} \mathrm{H}_{5}$

Example 3

Polystyrene is produced commercially by reaction of styrene with butyllithium as an anionic initiator. Using resonance structures, explain how the chain-carrying intermediate is stabilized.

Example 4

Vinylidene chloride, $\mathrm{H}_{2} \mathrm{C}=\mathrm{CCl}_{2}$, does not polymerize in isotactic, syndiotactic, and atactic forms. Explain.

Example 5

Polymers such as polypropylene contain a large number of chirality centers. Would you therefore expect samples of isotactic, syndiotactic, or atactic polypropylene to rotate plane-polarized light? Explain.

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Step-by-Step Explanations

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Common Mistakes

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