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17.
Given a diene and dienophile, write the structure of the resulting cycloaddition
(Diels-Alder) adduct.
18.
Given the structure of a cyclic compound that can be synthesized by the Diels-Alder
reaction, deduce the structures of the required diene and dienophile.
19.
Given an alkyne, write the structures of products obtained by adding one or two
moles of a particular reagent to it.
20.
Write the steps in the mechanism of ethylene polymerization catalyzed by a free
radical.
21.
Write the structure of the alcohol produced from the hydroboration-oxidation
sequence when applied to a particular alkene.
22.
Given an alkene or cycloalkene (or diene, and so on), write the structures of the
expected ozonolysis products.
23.
Given the structures of ozonolysis products, deduce the structure of the unsaturated
hydrocarbon that produced them.
24.
Draw orbital pictures for a double bond and a triple bond.
25.
Draw conventional structures for the contributors to the resonance hybrid of an allyl
cation.
26.
Describe simple chemical tests that can distinguish an alkane from an alkene or
alkyne.
27.
Know the meaning of: cracking, alkylation, isomerization, platforming, and octane
number as applied to petroleum refining.
ANSWERS TO PROBLEMS
Problems Within the Chapter
3.1
The formula C 4 H 6 corresponds to C n H 2 n- 2 . The possibilities are one triple bond, two
double bonds, one double bond and one ring, or two rings.
acyclic
cyclic
3.2
Compounds a and c have alternating single and double bonds, and are conjugated.
In b and d, the double bonds are isolated.
3.3
a.
b.
2-chloropropene
2-methyl-3-ethyl-2-butene
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