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

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Summary

Learning Objectives

Key Concepts

Example Problems

Explanations

Common Mistakes

Summary

Amines, organic derivatives of ammonia, are widely varied in structure—from simple alkylamines to complex heterocyclic systems—and are critically important in both biological and industrial chemistry. Their classification (primary, secondary, tertiary) is based on the number of substituents attached to nitrogen, which greatly influences their reactivity and basicity. Through diverse synthetic methods such as SN2 alkylation, reductive amination, and Hofmann elimination, and using analysis tools like IR, NMR, and mass spectrometry, chemists are able to both synthesize and characterize these compounds. Recognizing how substituents and aromaticity affect basicity is crucial for designing effective synthesis routes and understanding biochemical functionalities.

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

Name the following compounds: $$\text { (a) } \mathrm{CH}_{3} \mathrm{NHCH}_{2} \mathrm{CH}_{3}$$ b) c) d) e) f)

Example 2

Draw structures corresponding to the following IUPAC names: (a) Triisopropylamine (b) Diallylamine (c) $N$ -Methylaniline (d) $N$ -Ethyl- $N$ -methylcyclopentylamine (e) $N$ -Isopropylcyclohexylamine (f) $N$ -Ethylpyrrole

Example 3

Draw structures for the following heterocyclic amines: (a) 5 -Methoxyindole (b) 1,3 -Dimethylpyrrole (c) $4-(N, N$ -Dimethylamino)pyridine (d) 5-Aminopyrimidine

Example 4

Which compound in each of the following pairs is more basic? (a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}$ or $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CONH}_{2}$ (b) $\mathrm{NaOH}$ or $\mathrm{CH}_{3} \mathrm{NH}_{2}$ (c) $\mathrm{CH}_{3} \mathrm{NHCH}_{3}$ or pyridine

Example 5

The benzylammonium ion $\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{NH}_{3}^{+}\right)$ has $\mathrm{pK}_{\mathrm{a}}=9.33,$ and the propyl-ammonium ion has $\mathrm{pK}_{\mathrm{a}}=10.71$. Which is the stronger base, benzylamine or propylamine? What are the $\mathrm{pK}_{\mathrm{b}}$ 's of benzylamine and propylamine?

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