Suggested Mechanism Problems for 2.

222
The book “Organic Reaction Mechanisms: Selected Problems and Solutions” by
William C. Groutas provides 210 excellent practice questions on reaction
mechanisms. It also provides very nice “Minireviews” of key topics, and a
summary of the grammar and syntax of organic reaction mechanisms. It is an
excellent study tool for the student who is truly serious about doing well in 2.222,
and perhaps continuing on in organic chemistry.
All of the first 100 questions are relevant to this course, as are many of the
problems from 101 to 200. They vary in difficulty, and they are not presented in
order of difficulty.
Some problems from Groutas will appear on the tests and the final exam,
although I will choose from among the shorter and simpler problems in the
book.

Problems related to carbocation chemistry

1, 2, 5, 6, 7, 13, 18, 19, 20, 22, 26, 30, 33.

Problems related to acids, bases and nucleophiles (reactions

from 2.221 that you should know - plus some new ones)
35, 36, 37, 39, 45, 49, 50.

Problems related to nucleophilic additions to aldehydes and

ketones
52, 53, 57, 59, 62, 63, 65.

Problems related to acyl substitution reactions

72, 73, 74, 76, 78, 79, 82, 83, 97, 100.

“Grab bag” problems – a bit more challenging

101, 110, 124, 126, 131, 132, 133, 137, 143, 154, 162, 177, 184.