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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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.

Question: When N-bromosuccinimide is added to hex-1-ene in and a sunlamp is shone on the mixture, three products result.
Question: Draw another resonance form for each of the substituted allylic cations shown in the preceding figure, showing how the positive charge is shared by another carbon atom. In each case, state whether your second resonance form is a more important or less important resonance contributor than the first structure. (Which structure places the positive charge on the more-substituted carbon atom?)
What dienes and dienophiles would react to give the following Diels-Alder products?
a)

b)

c)

d)

e)

f)

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