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Chapter 28 851
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b. 1.
CH
2
CH
2
H
CH
2
CH
3
CH
2
CH
2
H
CH
3
CH
2
O
CH
3
O
H
CH
tautomerization
3
HO
CH
3
2.
3.
4.
13.
a.
and
b.
O
14
C
O
H
OH
14
C
14
C
tautomerization
14.
If a nondeuterated reactant had been used, the product would be identical to the reactant. Therefore, the
rearrangement would not have been detectable.
15.
A suprafacial rearrangement can take place under photochemical conditions if there are an even number of
electrons in the reacting system. Therefore, a 1,3-hydrogen shift occurs involving four electrons.
CD
2
D
a [1,3] sigmatropic
migration of deuterium
hv
CD
2
D
A suprafacial rearrangement can take place under thermal conditions if an odd number of electrons are in
the reacting system. Therefore, a 1,5-hydrogen shift occurs involving six electrons.
CD
2
D
a [1,5] sigmatropic
migration of deuterium
CD
2
D