1.

Classify each substituent as electron donating or electron withdrawing

a. Electron donating
b. Electron withdrawing

a. Electron donating
b. Electron withdrawing
c. Electron donating

2. Draw the products of each reaction.

3. Draw the products formed when each compound is treated with HNO3 and H2SO4. State
whether
the reaction occurs faster or slower than a similar reaction with benzene.

a.

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 b.

c.

d.

e.

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 4. Draw all resonance structures for the carbocation formed by ortho attack of the electrophile
+NO2 on
each starting material. Label any resonance structures that are especially stable or unstable

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 5. Draw the products of each reaction.

6. Draw the products formed from nitration of each compound

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 a

.
b.

7. Draw the products formed when each compound is treated with HNO3 and H2SO4.

a.

b.

c.

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 d.

8. Devise a synthesis of each compound from the indicated starting material.

a.

b.

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 c.

9. Write out the two-step sequence that converts benzene to each compound:
(a) C6H5CH2CH2CH2CH2CH3; (b) C6H5CH2C(CH3)3.

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 10. What steps are needed to convert benzene into p-isobutylacetophenone, a synthetic
intermediate
used in the synthesis of the anti-infl ammatory agent ibuprofen.

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