This schedule is tentative and subject to change in consultation with students.

We will be covering Grossman's The Art of Writing Reasonable Organic Reaction Mechanisms according to the following schedule. You are expected to do the reading and problem assignments before class.

Go to the next meeting after

Enter date as "mm/dd".

"Lecture" Date Topic Reading assignment (through page...) Problems
Intro to course; bonding theories and computational chemistry
acids, bases, curly arrows Chapter 1 (25) 1, 2, 5
classes of mechanisms Chapter 1 (43) 3, 4
SN2 vs. elimination under basic conditions Chapter 2 (58) 2a, 2e, 2i, 2r, 2s, 2bb
(conjugate) addition to carbonyl compounds Chapter 2 (69) 2d, 2h, 2j, 2k, 2q, 2u, 2y
nucleophilic substitution at sp2 centers; singlet carbenes Chapter 2 (80) 2b, 2c, 2f, 2o, 2p, 2z, 2aa
2c, 2g, 2l, 2m, 2z, 2cc, 2dd
free-radical and related substitution; singlet carbenes; base-promoted rearrangement Chapter 2 (92) 2g, 2l, 2m, 2n, 2t, 2w, 2cc, 2dd
2b, 2f, 2n, 2o, 2p, 2t, 2w, 2aa
two multistep reactions Chapter 2 (97) 1, 2v, 2x, 2ee, 2ff, 2gg, 3, 4
catch-up and review Chapter 2 bring Ch2 problems you have trouble with
carbocations: generation and rearrangement Chapter 3 (117) 1, 3
SN2/SN1 vs. E1 under acidic conditions; electrophilic addition and substitution Chapter 3 (131) 4b, 4f, 4g, 4j, 4k, 4n, 4o, 4q, 4s, 4t, 4u, 4y
nucleophiles and electrophilic p-bonds Chapter 3 (141) 4a, 4c, 4d, 4e, 4h, 4i, 4l, 4m, 4p, 4r, 4v, 4w
catch-up and review Chapter 3 2, 4x, 4z, 4aa, 4bb, 4cc, 4dd
Catch-up and review
Midterm exam
Spring Break -- no classes
review midterm exam
further review
introduction to pericyclic reactions and polyene molecular orbitals Chapter 4 (156) 1 (name mechanisms only)
Electrocyclic reactions Chapter 4 (169) 1(photo/thermal), 3, 6b, 6r, 6ii
typical cycloaddition reactions Chapter 4 (182) 6a, 6c, 6f, 6g, 6i, 6j, 6l, 6m
regio- and stereo-chemistry of cycloaddition Chapter 4 (195) 6n, 6p, 6s, 6t, 6u, 6v, 62, 6x
sigmatropic rearrangements Chapter 4 (209) 4, 5, 6d, 6e, 6o, 6q, 6z
ene reactions, catch-up Chapter 4 (215) 6h, 6k, 6y, 6aa, 6bb, 6cc
review mechanisms Chapter 4 6dd, 6ee, 6ff, 6gg, 6hh
bring problems you have difficulty with
introduction to free radicals Chapter 5 (238) 1 (see p. 242 for definition of "autoxidation"), 2, 3b
free-radical chain reactions Chapter 5 (252) 3a, 3f, 3h, 3j, 3l, 3n, 3p, 3r, 3s, 3v
non-chain free-radical and triplet reactions Chapter 5 (264) 3c, 3d, 3e, 3g, 3i, 3k, 3m, 3o, 3q, 3u
review Chapter 5 mechanisms Chapter 5 (264) 3t, 3w-3ee, 4
Final exam, 9 AM