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Organic Chemistry

Chapter 14

Organic ChemistryChapter 14

Chapter 14

Problem 14-1
Expected ΔH°hydrog for allene is −252 kJ/mol. Allene is less stable than a nonconjugated diene, which is less stable than a conjugated diene.
Problem 14-2
1-Chloro-2-pentene, 3-chloro-1-pentene, 4-chloro-2-pentene
Problem 14-3
4-Chloro-2-pentene predominates in both.
Problem 14-4
1,2 Addition: 6-bromo-1,6-dimethylcyclohexene 1,4 Addition: 3-bromo-1,2-dimethylcyclohexene
Problem 14-5
Interconversion occurs by SN1 dissociation to a common intermediate cation.
Problem 14-6
The double bond is more highly substituted.
Problem 14-8
Good dienophiles: (a), (d)
Problem 14-9
Compound (a) is s-cis. Compound (c) can rotate to s-cis.
Problem 14-13
300–600 kJ/mol; UV energy is greater than IR or NMR energy.
Problem 14-14
1.46 × 10−5 M
Problem 14-15
All except (a) have UV absorptions.
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