John E. McMurry
ISBN #9781285842912
3rd Edition
1,528 Questions
Homework Questions
This chapter covers the unique nature of aromatic compounds, emphasizing benzene’s stability due to delocalized ? electrons and resonance stabilization according to the Hückel 4n+2 rule. It details the mechanisms and variations of electrophilic aromatic substitutions—including halogenation, nitration, sulfonation, and Friedel–Crafts reactions—as well as nucleophilic aromatic substitution and side-chain oxidations. Additionally, the text explains how substituent effects (inductive and resonance) influence reactivity and directing outcomes, and it introduces strategic retrosynthetic planning for synthesizing polysubstituted aromatic compounds.
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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. •
Tell whether the following compounds are ortho-, meta-, or para-disubstituted: a. b. c.
Give IUPAC names for the following compounds: a. b. c. d. e. f.
Draw structures corresponding to the following IUPAC names: (a) $p$ -Bromochlorobenzene (b) $p$ -Bromotoluene (c) $m$ -Chloroaniline (d) 1 -Chloro-3,5-dimethylbenzene
Pyridine is a flat, hexagonal molecule with bond angles of $120^{\circ} .$ It undergoes substitution rather than addition and generally behaves like benzene. Draw a picture of the $\pi$ orbitals of pyridine to explain its properties. Check your answer by looking ahead to Section $9-4$.
To be aromatic, a molecule must have $4 n+2 \pi$ electrons and must be planar for cyclic conjugation. Cyclodecapentaene fulfills one of these criteria but not the other and has resisted all attempts at synthesis. Explain.