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398 CARBOXYLIC ACIDS AND THEIR DERIVATIVES
17.17 (a) The oxygen-oxygen bond of the diacyl peroxide has a low homolytic bond dissociation
energy (DH◦ ∼ 139 kJ mol−1). This allows the following reaction to occur at a moderate
temperature.
ΔH° 139 kJ mol−12
R
O
OO OR
O
R
O
(b) By decarboxylation of the carboxyl radical produced in part (a).
R CO2+R
O
O
(c)
Step 2
Step 1
R CO2+
Step 3 R +
Chain Initiation
Chain Propagation
heat
Step 4
Steps 3, 4, 3, 4, and so on.
+
2 R
O
O
R
RR
R
O
O
O OR
O
R
O
Problems
Structure and Nomenclature
17.18
O
OH(a)
O
NH2(b)
O
N(c)
O
OH
(d)
[ the (Z) isomer ]