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Ian R Gould  > igould@asu.edu CHM 234 : General Organic Chemistry II  > Spring 2012
 CHM 234/238
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Summarized here are the suggested textbook problems that correlate with the notes sections

     
I have fewer self-written problems for second semester organic (234) compared to first (233), also, second semester organic tends to be more conventional in terms of the material covered, and so the textbook problems are a more valuable study resource this semester compared to last. The problems summarized here appear at the end of each chapter of the 3rd Edition of the Smith textbook, for example, problem 15.40 is at the end of Chapter 15, etc.
Retrosynthesis
Making bromides and alkenes: 15.37, 15.40 (b, d), 15.45, 15.48 (c, d, e, f, g, h, i), 15.51 (a, d), 8.27, 8.35, 9.49
Synthesis and Retrosynthesis: 7.79, 7.80 , 7.82, 15.62 (b, c, d, f, h, i), 15.63 (a, b), 15.64 (b only)
Alkynes
Making alkynes, alkyne properties and reactions: 11.27, 11.28, 11.36, 11.37, 11.39, 11.40, 11.41, 11.44, 11.45, 11.48, 12.40 (a, b, c), 15.64
Mechanisms: 11.33, 11.34, 11.35, 11.52, 11.54, 11.55 (b), 11.57
Synthesis and Retrosynthesis: 11.58, 11.59, 11.60, 11.62, 11.64, 11.67, 15.64
Alcohols
Making alkynes, alkyne properties and reactions: 9.40, 9.42 (a, b, c, d, i), 9.47 (b, d, e, f, g, i), 9.48 (a, c), 9.51, 9.52 (not b, and ignore stereochemistry in c), 9.53 (a, b), 12.32, 12.41 (a, b, c, g), 12.42 (a, b, c, d), 12.43, 12.44 (d only), 20.39 (a, b, c, e, j, k), 20.40 (a, b, c, e, j, k)
Mechanisms: 9.54, 9.57, 9.63, 9.64
Synthesis and Retrosynthesis: 10.72, 12.69 (a, b, d), 12.70, 12.71
Organometals
Reactions: 20.39 (g, h), 20.40 (g, h), 20.41 (b, e), 20.42 (a, b, c, d, e, f, g, j, k), 20.45 (a, c, e), 20.49 (a, b), 20.50 (b, d, e, f, i), 20.51 (a, c, h)
Mechanisms: 20.56 (a only)
Synthesis and Retrosynthesis: 20.59, 20.60, 20.61, 20.62, 20.64, 20.66 (a, c)
Ethers/Epoxides
Making ethers/epoxides, properties and reactions: 9.41 (a, b, c, f), 9.47 (h), 9.48 (g), 9.65, 9.66, 9.67, 9.70 (a, b, c, d, e), 9.71
Mechanisms: 9.68, 9.73
Synthesis and Retrosynthesis: 9.76 (c), 9.77 (c), 20.66 (c)
Conjugated Systems
Reactions, Properties: 16.31, 16.34, 16.44, 16.45, 16.47, 16.48, 16.49, 16.51, 16.52, 16.54, 16.55, 16.59, 16.62, 16.63
Pericyclic Reactions: C1, C3 (ignore excited state), C4 (Ignore excited state), C13, C14, C15, C20 (these problems are in the Pericyclic Reactions Supplement, Click HERE)
Mechanisms: 16.61
Synthesis and Retrosynthesis: 16.58
Aromatic Systems
Properties: 17.32, 17.33, 17.34, 17.39, 17.42, 17.47, 17.49
Benzenes
Reactions, Properties: 17.29, 18.35 (a - g, i, k, l), 18.36 (a, b, c, e), 18.37, 18.38 (not c), 18.41 (a, b, c, d, f), 18.43, 18.44, 18.47
Mechanisms: 18.52, 18.53, 18.54, 18.56, 18.61
Synthesis and Retrosynthesis: 18.62, 18.63, 18.64, 18.79, 18.76, 18.77, 20.69, 20.71
Aldehydes and Ketones
Reactions, Properties: 21.42 (a, b, c, e, f, h, j, k, l), 21.43, 21.45 (a, b, c, d, e, f, g, h, i, j), 21.46 (a, b, c, d), 21.47, 21.48, 21.49, 21.51 (a, b, c, d, f, g, h), 21.52, 21.53, 21.57
Mechanisms: 21.73, 21.76, 21.77, 21.81
Synthesis and Retrosynthesis: 20.66 (g, h), 21.60, 21.61, 21.63 (a, d, e), 21.64, 21.66 (not e), 21.67, 21.69, 21.71, 20.72 (a, b, c, e)
Enols/Enolates
Reactions, Properties: 23.30, 23.33, 23.34, 23.36, 23.39, 23.40, 23.44, 23.54 (c, d, e, h, i), 23.55, 24.27, 24.29, 24.30, 24.35, 24.37, 24.39, 24.46 (c, d)
Mechanisms: 23.46, 23.60, 23.72, 24.53, 24.54
Synthesis and Retrosynthesis: 23.47, 23.48, 23.49, 23.64 (a, c, d), 23.65 (a, c, d), 23.68 (a, b), 24.31, 24.33, 24.38, 24.60, 24.62
Carboxylic Acids
Reactions, Properties: 22.48 (a, b, c, e, g, h), 22.52 (a, g, i), 22.55 (b), 22.71
Acid Derivatives
Reactions, Properties: 22.43, 22.44, 22.46 (c, d, e), 22.47 (b, e), 22.48 (b, c, e, k, i), 22.51 (a, c, f), 22.52 (a, b, f, g, h, k), 22.53
Mechanisms: 22.57, 22.59, 22.62, 22.63, 22.64
Synthesis and Retrosynthesis: 22.69, 22.70 (c, d, f, h), 22.71, 22.74, 22.75, 22.76
Amines
Reactions, Properties: 25.41, 25.45, 25.46, 25.52, 25.54, 25.55, 25.56, 25.57 (NaBH3CN serves the same purpose as H2/Pd/C), 25.60 (a, b, e, f, g), 25.62 (a, b, d, f), 25.63, 25.68