Lecture schedule,

We will be covering Bruice's Organic Chemistry 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 Problems
Intro to course:
review of concepts: Lewis structures, octets, VSEPR
Bonding & Lewis structures:
condensed structures and line-bond structures 		1.1-1.4
review VSEPR from Gen Chem 		You may ignore "hybridization"
68, 69, 71, 75, 78, 85, 86, 90, 93
isomers and alkane nomenclature: roots and prefixes
homologs, isomers, substituents 		2.1-2.2 45f,i,m,n,o; 46(1,4,6); 47, 49, 50e, 52, 54e,h,j,k; 56, 61a,d,g; 66b,d,e,f;
nomenclature: prefixes and suffixes
cycloalkanes, halides, ethers, alcohols, amines; skeletal structures; primary etc 		2.3-2.7
Formal structure of IUPAC names
Nomenclature handout #1 		45a-e,g,h,j,k,l; 46(2,3,5,7-11); 50a-d,f-j; 54a-d,f,g,i,l; 57, 60, 61b,c,e,f,h,i; 64, 66a,c; 69
structure & properties of saturated compounds
cis/trans isomers, structure-property relationships, bond rotation; epoxide nomenclature 		2.8-2.10 51, 53, 59, 63, 70
alkene structure & nomenclature
infixes and suffixes; cis/trans stereoisomers; E/Z nomenclature 		3.1-3.5 34, 35, 36, 37, 38, 40, 44, 46, 47, 48
alkyne structure & nomenclature
nomenclature with two infixes 		6.1-6.2 25, 27, 29, 30, 34, 39, 49
functional groups and identifying them
names of functional groups 		see table, inside back cover see problems for next class day
nomenclature of substituted benzenes 14.8, 15.1
see also Aromatic Nomenclature handout 		14.30; 15.34(except e), 35(except i)
nomenclature of functional groups: prefixes and suffixes; priority rules; heterocyclic nomenclature 16.1, 17.1, 20.1; also the ring names on page 646 (14.4)
nomenclature handout #2 		16.45, 46(except c,i); 17.45; 20.26
chirality and stereoisomers
chirality; enantiomers; R/S nomenclature; introduction to Fischer projections 		5.1-5.7
Chirality module
practice with R and S
Fischer projection module with exercises
see also this online drill series and Drawing 3D structures in 2D 		58, 59, 60, 61, 62, 73, 75; 16.46c,i
optical activity; compounds with more stereocenters
enantiomeric excess; diastereomers and meso compounds 		5.8-5.12 63, 66, 67, 71, 72, 74, 78, 81, 82, 86
Exam 1 review
nomenclature & reactivity of chiral compounds
naming more than one stereocenter; how stereocenters affect reactivity 		5.13-5.17 65, 79, 80, 83, 84, 89, 94
Fischer projections 5.90
Fall Break -- no classes
organic acids and bases
polar bonds, dipoles, pKa 		1.15-1.19; Appendix II
pKas you should know 		73, 76, 89, 92
organic acids and bases; curved arrows
structure-reactivity relationships; Lewis acids & bases 		1.20-1.26; 3.6
for practice, go to Curly Arrows 		1.74, 79, 81, 82, 84, 87, 88, 89, 91
alkene reactions: electrophilic addition
carbocations & regioselectivity 		3.6, 4.1, 4.2, 4.4 4.37, 43, 45, 47a,f, 49, 52, 54, 58-61
alkene reactions: hydration & hydrohalogenation
methods of hydration; epoxidation (nomenclature handout) 		4.5, (4.6), 4.7-4.9 40, 47b,c,d,e,g,h, 55
alkene reactions and organic synthesis
hydroboration; hydrogenation; introduction to synthesis 		4.10-4.12 38, 39, 41, 42, 44, 46, 48, 50, 57
reaction stereochemistry
stereochemistry of electrophilic addition 		5.18-5.21 64, 68, 69, 70, 77, 85, 87, 88, 91, 92, 93, 96
alkyne reactions
alkyne reactions compared to alkenes 		6.3-6.7
keto-enol equilibria 		24, 40, 43
alkyne reactions and synthesis 6.8-6.12 26, 28, 31, 32, 33, 36, 37, 38, 41, 42, 44, 45, 46
Exam 2 review
localized and delocalized bonding
resonance contributors & hybrids 		7.1-7.5
see also Curly Arrows 		6.47, 50; 7.40, 41, 43, 45, 46, 47, 49, 50, 53
delocalization and reactivity
delocalization energy; pKa and other reactivity effects 		7.6, 7.7, 7.9, 7.10
pKas you need to know 		42, 44, 48, 51, 52, 54, 55, 56, 57, 58
nucleophilic substitution reactions
the SN2 reaction and the SN1 reaction 		8.1-8.5
animations of nucleophilic substitution and elimination reactions 		33, 35, 36, 37, 39, 40, 42, 49, 56
elimination reactions
E2 and E1 reactions 		9.1-9.4
animations of nucleophilic substitution and elimination reactions 		31, 32, 37a,b,e,f, 40, 44, 47, 50
converting alcohols into leaving groups
making alkyl halides; making sulfonate esters 		10.1-10.3 43a,b,c,h, 47, 56, 71, 76
substitution on alcohols, ethers and epoxides
dehydration and oxidation of alcohols; reactions of ethers vs epoxides 		10.4-10.8; 19.2
the Swern oxidation 		43d,f,g, 44, 48, 49a-e, 52, 54, 57, 58, 60, 61, 63, 64, 65, 66, 72
miscellaneous alcohols, ethers and analogs
thiols and sulfides 		10.9-10.12 43i, 46, 49f,g,i, 51, 53, 67, 68, 69, 70
nucleophilic acyl substitution
reactions of acyl halides; anhydrides; esters 		16.2-16.10
reactions of carbonyl compounds 		47, 48, 50, 52, 58, 61, 82, 83, 84, 86, 87
acid- & base-catalyzed nucleophilic acyl substitution
reactions of esters, acids and amides 		16.11-16.17 53, 54, 55, 57, 59, 67, 68
using imides and nitriles in synthesis
making primary amines; ring synthesis; activating acids 		16.18-16.23 49, 63, 64, 66, 69, 72, 76, 78, 79, 80, 81
reactivity of aldehydes and ketones 17.2-17.4
reactions of carbonyl groups 		47, 52, 61, 76
Exam 3 review
Thanksgiving Break -- no classes
nucleophilic acyl addition & carbonyl substitution
reactions with nucleophiles and ambiphiles 		17.5-17.8 46(except g), 48, 59, 69, 70, 77
hydrates, hemiacetals and acetals
reactions with water and alcohols 		17.9-17.10 46g, 49, 50, 51, 53(all but c), 56, 58, 71
Exam 3 retake (in class) -- You must take the makeup exam on this date.
preparation of monosubstituted benzenes
electrophilic aromatic substitution 		14.9-14.15 32, 37, 43, 48
reactions of aryl substituents 14.16, 14.18-14.19 41, 42, 45, 46, 47
Catch-up and review
Final Examination, 9:00 AM