Chapter 15: Q 1P (page 754)
Rank each group of compounds in order of increasing heat of hydrogenation.
(a) Hexa-1,2-diene; hexa-1,3,5-triene; hexa-1,3-diene; hexa-1,4-diene; hexa-1,5-diene; hexa-2,4-diene.
(b)

Short Answer
a)

b)

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Chapter 15: Q 1P (page 754)
Rank each group of compounds in order of increasing heat of hydrogenation.
(a) Hexa-1,2-diene; hexa-1,3,5-triene; hexa-1,3-diene; hexa-1,4-diene; hexa-1,5-diene; hexa-2,4-diene.
(b)

a)

b)

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One milligram of a compound of molecular weight 160 is dissolved in 10 mL of ethanol, and the solution is poured into a 1-cm UV cell. The UV spectrum is taken, and there is an absorption at 饾泴max= 247 nm.The maximum absorbance at 247 nm is 0.50. Calculate the value of饾泦 for this absorption.
Predict the products of the following proposed Diels-Alder reactions.
a)

b)

c)

d)

e)

f)

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 Br2 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.
In a strongly acidic solution, cyclohexa-1, 4-diene tautomerizes to cyclohexa-1, 3-diene. Propose a mechanism for this rearrangement, and explain why it is energetically favorable.
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