Chapter 15: Q 14P (page 772)
Predict the products of the following proposed Diels-Alder reactions.
a)

b)

c)

d)

e)

f)

Short Answer
a)

b)

c)

d)

e)

f)

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Chapter 15: Q 14P (page 772)
Predict the products of the following proposed Diels-Alder reactions.
a)

b)

c)

d)

e)

f)

a)

b)

c)

d)

e)

f)

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Question: When is added to buta-1,3- diene at -150C, the product mixture contains 60% of product A and 40% of product B. When the same reaction takes place at 600C, the product ratio is 10% A and 90% B.
a. Propose structures for products A and B (Hint: In many case, an allylic carbocation is more stable than a bromonium ion.)
b. Propose a mechanism to account for formation of both A and B.
c. Show why A predominates at -150C and B predominates at 600C .
d. If you had a solution of pure A, and its temperature were raised to 600C , what would you expect to happen ? Propose a mechanism to support your prediction.
Show how you might synthesize the following compounds starting with bromobenzene, and alkyl or alkenyl halides of four carbon atoms or fewer.
a. 3-phenylprop-1-ene
b.5-methylhex-2-ene
c. dec-5-ene
Question: When 3-bromo-1-methylcyclohexene undergoes solvolysis in hot ethanol, two products are formed. Propose a mechanism that accounts for both of these products.

In Solved Problem 15-2, we simply predicted that the products would have a 1, 2-or 1, 4-relationship of the proper substitutents. Draw the charge-separated resonance forms of the reactants to support these predictions.
Predict the products of the following Diels-Alder reactions.
a)

b)

c)

d)

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