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

The chapter illustrates that the complex metabolic pathways in living organisms follow the same fundamental organic reaction mechanisms encountered in laboratory chemistry. Major pathways including glycolysis, beta-oxidation, the citric acid cycle, gluconeogenesis, and protein deamination are interconnected through common intermediates such as acetyl CoA, which is central to energy production. Moreover, a discussion of pericyclic reactions underscores that concerted processes governed by orbital symmetry rules are not only relevant in synthetic organic chemistry but also in certain biological transformations such as vitamin D synthesis.

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

One of the steps in fat metabolism is the reaction of glycerol $(1,2,3$ -propanetriol) with ATP to yield glycerol 1-phosphate. Write the reaction, and draw the structure of glycerol 1-phosphate.

Example 2

Write the equations for the remaining passages of the $\beta$ -oxidation pathway following those shown in Figure $29-4$

Example 3

How many molecules of acetyl CoA are produced by catabolism of the following fatty acids, and how many passages of the $\beta$ -oxidation pathway are needed? (a) Palmitic acid, $\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{14} \mathrm{CO}_{2} \mathrm{H}$ (b) Arachidic acid, $\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{18} \mathrm{CO}_{2} \mathrm{H}$

Example 4

Write a mechanism for the dehydration reaction of $\beta$ -hydroxybutyryl ACP to yield crotonyl ACP in step 7 of fatty-acid synthesis.

Example 5

Evidence for the role of acetate in fatty-acid biosynthesis comes from isotopelabeling experiments. If acetate labeled with $13 \mathrm{C}$ in the methyl group $\left({ }^{13} \mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\right)$ were incorporated into fatty acids, at what positions in the fattyacid chain would you expect the ${ }^{13} \mathrm{C}$ label to appear?

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Step-by-Step Explanations

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Common Mistakes

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