Chapter 15: Q21P (page 477)
Draw and name all possible aromatic compounds with the formula C7H7Cl.
Short Answer
Answer
(I)

Chloromethyl benzene
(II)

o-chlorotoluene.
(III)

m-chlorotoluene
(IV)

p-chlorotoluene.
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Chapter 15: Q21P (page 477)
Draw and name all possible aromatic compounds with the formula C7H7Cl.
Answer
(I)

Chloromethyl benzene
(II)

o-chlorotoluene.
(III)

m-chlorotoluene
(IV)

p-chlorotoluene.
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Thiamin, or vitamin B1, contains a positively charged five-membered nitrogen–sulfur heterocycle called a thiazolium ring. Explain why the thiazolium ring is aromatic.

Draw all of the resonance forms for each. What patterns emerge?

7 Propose structures for aromatic compounds that have the following NMR spectra:
(a)

b)

c)

Show the relative energy levels of the seven p molecular orbitals of the cycloheptatrienyl system. Tell which of the seven orbitals are filled in the cation, radical, and anion, and account for the aromaticity of the cycloheptatrienyl cation.
Azo dyes are the major source of artificial color in textiles and food. Part of the reason for their intense coloring is the conjugation from an electron-donating group through the diazo bridge to an electron-withdrawing group on the other side. For the azo dyes below, draw a resonance form that shows how the electron-donating group is related to the electron-withdrawing group on the other side of the diazo bridge. Used curved arrows to show how the electrons are reorganized.
a.
Methyl orange
b.
C.I. Acid Red 74
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