TEXTBOOK: Solomons & Fryhle, Organic Chemistry, eighth edition with Study Guide ISBN 0-471-47246-8
The numbers are the section numbers of the text that that should be read.
These sections correspond to the material covered in lectures.
The numbers after "Problems" are problem assignments.
Chapter 1, Chemical Bonding
Readings - All material except antibonding orbitals on p 23–25
Problems - 1 – 6, 8, 12 –17, 19 – 23, 25
Optional Problems - 7, 33, 34, 39
Chapter 2, Functional Groups
Readings - All except Section 2.16
Problems - 1, 3, 5 – 7, 11 – 13, 17, 18, 20 – 23, 25 – 28, 32 – 35, 37, 42
Optional Problems - 4, 8, 9, 16, 36, 41, 48
Chapter 3, Acid and Bases
Readings - All of the chapter
Problems - 1 – 4, 6 – 11, 14 – 25, 27, 29, 31 – 35, 40
Optional Problems - 5, 12, 13, 26, 28, 30, 36, 39
Chapter 4, Alkanes
Readings - Sections 4.1, 4.1A-4.1C, to get the general idea, 4.2 - 4.4A, 4.4B, to get the general idea, 4.5 -4.12, 4.12A, to get the general idea, 4.13 - 4.14, 4.15, to get the general idea, 4.16, 4.17A, 4.17C -4.18, 4.19, to get the general idea (examples will be covered later)
Problems - 1, 2, 4, 5, 7 – 9, 11 – 13, 19, 22, 27, 29, 30, 32, 35, 37, 44, 45
Optional Problems - 10,15, 20, 31, 34, 39 – 41, 46, 51, 54, 56
Chapter 5, Stereochemistry
Readings - Sections 5.1 -5.10A, 5.10B - 5.11 to get the general idea, 5.12 - 5.15, 5.16 - 5.18 to get the general idea
Problems - 1, 2, 4, 7, 9, 11 – 14, 17 – 21, 24, 31, 33
Optional Problems - 5, 22, 23, 26, 35, 45
Chapter 6, Nucleophiles, Carbocations, etc.
The material on carbocation stability in section 6.11B is critical to understanding the material in chapter 8. The entire chapter should be read to refresh your memory of the topics covered in
Chemistry 123. Sections 6.15 – 6.18 can be skipped.
Problems - 1 – 4, 6, 9, 11, 13, 16, 24, 39
Optional Problems - 8, 14, 18, 20, 43
Chapter 7, Alkene and Alkyne chemistry
Readings - Sections 7.1- 7.4, 7.7, 7.10 - 7.15, except 7.14B
Problems - 1 – 3, 9, 14 – 17, 18, 20, 21, 25, 28, 32, 33, 37, 38
Optional Problems - 19, 24, 39 – 42, 46
Chapter 8, Addition Reactions of Alkenes and Alkynes, Acidity of Terminal Alkynes
Readings - Sections 8.1 - 8.2C, 8.5, 8.12 - 8.14, 8.18 - 8.19
Problems - 1 – 3, 5 – 7, 16, 24, 29 (not 29.bc and e), 32, 36
Optional Problems - 8, 15, 17, 35, 37, 43, 48, 50, 52
Chain Growth polymers (polyalkenes)
Page 485 - 489, section 23.3A
Problems - A.2, A3
Optional Problems - A.1, A.4
Chapter 13, Resonance
Readings - Sections 13.1 - 13.2, 13.2A to get the general idea, 13.3 -13.8, but ignore the discussion of nonbonding and antibonding orbitals on p 583, 586, 13.10 - 13-10A Kinetic vs. thermodynamic control
Problems - 1 – 6, 9, 10, 23, 34
Optional Problems - 18 (not 18f), 33, 38
Chapter 14, Aromatic Compounds
Readings - Sections 14.1 - 14.9 but skip Figs 14.4 and 14.6 and the related discussion of molecular orbitals. Also skip 14.7B NMR spectroscopy of aromatics.
Problems - 1, 2, 7 – 9, 12, 16, 22 and A1 on p 488
Optional Problems - 13, 17, 18, 20, 23
Chapter 15, Reactions of Aromatics
Readings - Sections 15.1 - 15.7, Skip Sections 15.8 – 15.11, Read 15.12A benzylic systems.
Problems - 1, 3
Optional Problems - 2, 4
Chapter 12, Grignard reagents
Readings - Sections 12.6-12.8
Problems - 7, 9
Optional Problems - 8, 10
Chapter 16, Aldehydes and ketones.
Readings - Sections 16.1 - 16.3, 16.5B, 16.6 - 16.9, but skip 16.7D thioacetals, 16.13
Problems - 1, 2, 4a, d–h, 5-14, 16, 23, 24a -d, g k m n, 25a b c g k m n,
28 all except i,q, 35, 49
Optional Problems - 3, 37, 40, 47
Chapters 18, 23 Carboxylic Acids and Their Derivatives
Readings - Sections 18.1 18.2I, 18.4 - 18.8F, 18.8H - 18.HI, 18.10, 23.1 - 23.2A, 23.2C
Problems - 1–3, 5abdi, 6bef, 7ab, 10, 11, 14, 16b, 19a–d, 20, 23ab, 24–e, 25ac, 29a–d, 30ab
Optional Problems - 4, 8, 9, 29f, 37, 39
Condensation Polymers
p 867 - 872 (polyesters and polyamides)
p 1167 (Polyamino acids, proteins)
Problems - p 871, B2– B5.
Optional Problems -
Chapter 17, Enolates and Aldol type reactions
Readings - Sections 17.1 - 17.5A, 17.6 -17.7
Problems - 1 – 14,18 – 22, 28a – d, f - i, 29a – d, f - i, 30 (not e,f,h), 31 (not c,g)
Optional Problems - 23, 28el, 29el, 42
Chapter 19, b-dicarbonyl compounds
Readings Sections 19.1 - 19.3A, 19.3C - 19.4, 19.6
Problems - 1 – 8, 10 – 14, 25 (not g,h)
Optional Problems - 15, 16, 26 (not a), 27 - 29, 32, 41, 45, 47, 48
Chapter 22, Carbohydrates
Readings - Sections 22.1 - 22.4, 22.6A - 22.6C, 22.7 - 22.13 (skip 22.9B), 22.11 only to get the general idea
Problems - 1 – 6, 11 – 13, 15, 20, 28
Optional Problems - 14, 17, 21, 27