Chapter 16 Homework Answers
Brown & Foote, pages 623 - 629 :
Problems 16.7 - 13 , 15 - 25 , 27 , 28 , 30 - 40
1. Give IUPAC names for the following:
a)
(1S,2R)-2-methylcyclopentanecarboxylic acid
Note - (cis) is correct but not specific enough to identify
this enantiomer
b)
(E)-3-oxo-5-methyl-4-heptenoic acid
(trans) would also be acceptable
2. Write a complete mechanism for the acid-catalyzed hydrolysis
of methyl acetate.
The mechanism is the exact reverse of Fischer esterification.
Note the beautiful symmetry of this mechanism.
3. Show two different ways to prepare cyclohexanecarboxylic
acid starting with cyclohexane.
The upper pathway is likely to be better because the SN2
displacement by CN- on the 2° alkyl bromide may be complicated
by some elimination.