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32.4.13: Chapter 14

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    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 14-7 A cyclohexene, in which C 1 and C 2 are bonded to methyl. C 4 is wedge bonded to C O 2 C H 3. C 5 is dash bonded to methyl.
    Problem 14-8 Good dienophiles: (a), (d)
    Problem 14-9 Compound (a) is s-cis. Compound (c) can rotate to s-cis.
    Problem 14-10 A cyclohexane is fused to a cyclohexene with the double bond between C1 and C2. There is a methyl at C 2. C 3 and C 4 of second ring are each wedge bonded to C O 2 C H 3.
    Problem 14-11 Polymer has n repeating units of of a 4-carbon chain, in which C 2 is double bonded to C 3 and a benzene ring at C 2.
    Problem 14-12 A two-step polymerization reaction mechanism of 1,3-butadiene with H plus (acid-catalyzed) shows the formation of a polymer.
    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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