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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The following molecular model is that of a carbocation. Draw two resonance structures for the carbocation, indicating the positions of the double bonds.

Draw the five resonance structures of the cyclopentadienyl anion. are all carbon-carbon bonds equivalent? How many absorption lines would you expect to see in the NMR and NMR spectra of the anion?
Give IUPAC names for the following compounds
b)

Propose structures for aromatic hydrocarbons that meet the following descriptions:
(a) C9H12; gives only one C9H11Brproduct on substitution of hydrogen on the aromatic ring with bromine
(b)C10 H14; gives only one C10H13Clproduct on substitution of hydrogen on the aromatic ring with chlorine
(c) C8H10; gives three C8H9Brproducts on substitution of hydrogen on the aromatic ring with bromine
(d)C10 H14 ; gives two C10H13Clproducts on substitution of hydrogen on the aromatic ring with chlorine
Anthracene has four resonance structures, one of which is shown. Draw the other three

Anthracene
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