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Unformatted text preview: Copyright 2011 JK Whitesell
17-12 What needs to be accomplished here is the cleavage of both a C-C σ and C=C π
bond. We know to this point only one reaction that accomplishes both: ozonolysis. Once
that is done, we then must reduce the resulting ketones.
17-18 We have learned that, all else being the same, ketones are more stable than are
aldehydes, and formaldehyde is the least stable. So the order given in the answer in the
book is logical on this basis except for the 3,3-dimethyl-2-butanone. There, steric
interactions in the HCN adduct decrease its stability.
17-19 To find the starting materials for the synthesis of an alkene by a Wittig reaction,
erase the middle of the π bond and then add an “O” to one side and a PPh3 to the other:
O It is generally best to have the phosphorous ylide on the less substituted carbon. ...
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