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.
| "Lecture" Date | Topic | Reading assignment | Problems |
| Intro to course | |||
| Mass spectrometry |
12.1-12.5; see also 3.1 Organic Chemistry Online Spectroscopy I: Mass Spectroscopy (all sections) |
3.42, 3.45, 6.35; 12.41, 47, 50, 52, 53, 55, 67 | |
| IR spectroscopy |
12.6-12.10
Organic Chemistry Online Spectroscopy I: Infrared Spectroscopy (all sections) |
42, 45, 48, 54, 58, 61, 62, 65, 68 | |
| IR spectroscopy |
12.11-12.15 Organic Chemistry Online Spectroscopy I: Infrared Spectroscopy (all sections) |
43, 49, 51, 56, 57, 60, 63, 66, 69 | |
| NMR theory |
13.1-13.6
Organic Chemistry Online Spectroscopy I: Proton & Carbon NMR: "Background" and "Chemical Shift" |
43a, 49, 68 | |
| 1H NMR: signals & splitting |
13.7-13.11
Organic Chemistry Online Spectroscopy I: Proton & Carbon NMR: "Spin Coupling", "Splitting" and "H-NMR Chart" |
44, 45, 47, 50, 51, 54, 56, 57, 58, 65, 66, 67 | |
| Martin Luther King Day -- no classes | |||
| 1H NMR: splitting patterns and structure |
13.12-13.16
Organic Chemistry Online Spectroscopy I: Proton & Carbon NMR: "Spin Coupling" and "Splitting" |
46, 48a,b,c,d,e,f,i,,j, 60, 61, 62, 63, 69, 70, 71 | |
| 13C NMR, DEPT & COSY |
13.17-13.22
Organic Chemistry Online Spectroscopy I: Proton & Carbon NMR: "Carbon NMR," "C-NMR Chart" and "The NOE" |
43b, 48g,h, 52, 53, 55, 59, 72, 73, 74 | |
| spectroscopy and structural identification |
3.1; Ch. 12-13 Organic Chemistry Online: Spectroscopy II |
12.69, 13.64, 16.56, 60, 65, 74 | |
| spectroscopy and structural identification |
3.1; Ch. 12-13 Organic Chemistry Online: Spectroscopy II |
13.71, 72; 15.63; 16.51, 70, 71 | |
| spectroscopy and structural identification |
3.1; Ch. 12-13 Organic Chemistry Online: Spectroscopy II |
13.56; 14.36; 15.41, 57, 62 | |
| In-class Examination | |||
| bonding and MO theory |
1.5-1.10
Organic Chemistry Online: Structure & Bonding "Ionic, Polar and Covalent Bonds," "Atomic & Molecular Orbitals" |
72, 88, 92, 95, 96, 97, 98, 99, 100 | |
| bonding and VB theory |
1.7-1.14
Organic Chemistry Online: Structure & Bonding "Valence & Hybridization," "Resonance" |
69, 70, 71, 77, 80, 83, 85, 86, 93, 101 | |
| bonding theory, pi molecular orbitals and aromaticity; hyperconjugation |
7.8; 14.1-14.7; see also 4.2
constructing MOs for conjugated molecules Organic Chemistry Online: McMurry TOC > 15. Benzene & Aromaticity "Aromaticity -- the 4n+2 rule" |
7.59, 79; 14.31, 33, 34, 38, 39, 40, 44
Organic Chemistry Online: McMurry TOC > 15. Benzene & Aromaticity "Aromaticity" |
|
| UV/VIS spectroscopy |
12.16-12.20 see also What are anti-bonding orbitals? |
6.48; 12.44, 46, 59, 64, 70; 14.49, 50 | |
| conformation, strain and cyclic compounds |
2.10-2.14
Organic Chemistry Online: McMurry TOC > 4. Stereochemistry of Alkanes and Cycloalkanes "Conformational Analysis" |
48, 58
Organic Chemistry Online: McMurry TOC > 4. Stereochemistry of Alkanes and Cycloalkanes "Conformational Stability" See Newman projections See also Dublin University's Conformational Analysis website, and Chair/boat cyclohexane |
|
| strain in cyclohexanes |
2.12-2.14
Organic Chemistry Online: McMurry TOC > 4. Stereochemistry of Alkanes and Cycloalkanes "Conformational Analysis" |
55, 62, 65, 67, 68, 71, 72, 73, 5.95
Organic Chemistry Online: McMurry TOC > 4. Stereochemistry of Alkanes and Cycloalkanes "Conformational Stability" See Dublin University's Conformational Analysis website, and Chair/boat cyclohexane |
|
| studying reactions: reaction coordinates & stability | 3.1, 3.7, 3.8, 4.3, 7.8, 7.11 | ||
| the Diels-Alder reaction | 7.12 | 61, 62, 64, 68, 69, 70, 71, 72, 74, 76, 77, 78 | |
| studying reactions: using rates and the structure of products | 8.10-8.12 | 44, 45, 46, 47, 48, 51, 52, 54, 55, 57, 58, 59, 60, 61 | |
| studying reactions: using rates and the structure of products | 9.5-9.7 | 33, 36, 37, 38, 41, 46, 48, 49, 52, 53, 54, 55, 56, 57 | |
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Mid-Term Examination review The Mid-Term examination is Wednesday, February 25, 2009, from 7 until 9 PM. |
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| Spring Break -- no classes | |||
|
synthetic methods: organometallic coupling reactions |
10.13 | 43, 45, 49, 55, 62 | |
| studying reactions: free-radical reactions | 11.1-11.5 | 21, 22, 23, 25, 27, 28, 30, 33, 34, 36, 37 | |
| free radicals in synthesis | 11.6-11.11 | 20, 24, 26, 29, 31, 32, 38, 39, 40 | |
| reactivity of substituted benzenes | 15.1-15.3 | 34(except h), 35(except i), 38, 40, 44, 55 | |
| substituent effects and their use in synthesis | 15.4-15.8 | 37, 39, 42(except d), 43, 46, 48, 51, 52, 53, 56, 64 | |
| diazonium salts in synthesis; formation of diazonium salts from amines; nucleophilic aromatic substitution | 15.9-15.14 | 34h, 35i, 36, 42d, 45, 47, 49, 50, 54, 58, 59 | |
| diazonium salts in synthesis; formation of diazonium salts from amines; nucleophilic aromatic substitution | 15.9-15.14 | 60, 61, 65, 66, 67, 68, 69, 70 | |
| reaction review | review chapters 16.1 through 17.10 | 16.72, 73, 75b,e,f, 76, 77, 82-88 | |
| In-class Examination | |||
| synthetic methods: protection, Wittig, synthons and disconnects | 17.11-17.15 | 53, 54, 55, 57, 63, 64, 65, 66, 68, 72, 73, 74, 75, 78, 79 | |
| Engagement Day -- service projects | |||
| carbonyl reactivity: α,β-unsaturated carbonyls and keto-enol tautomerism | 17.16-17.18, 18.1-18.3 | 17.60, 62, 67, 80, 81, 82, 83, 84; 18.51, 52, 56, 61, 77 | |
| reactions at the α-carbon: alkylation & acylation | 18.4-18.10 | 58, 63, 64, 73, 74, 78, 80 | |
| Named reactions: Michael, Aldol, Claisen, etc | 18.11-18.17 | 53, 57, 65, 67, 68, 69, 70, 71, 76, 83, 84 | |
| Good Friday -- no classes | |||
| Easter Monday -- no classes | |||
| putting it all together: malonic & acetoacetic ester syntheses | 18.18-18.22 | 48, 49, 50, 54, 55, 59, 60, 62, 66, 72, 75, 79, 81, 82, 85 | |
| amine chemistry: nomenclature, reactions and synthesis | 20.1-20.7 | 26, 27a,c,f, 28, 30, 33, 40, 42c,f,i, 43, 46, 48, 49 | |
| amine heterocycles | 20.8-20.10 | 27b,d,e,g,h,i, 29, 31, 32, 34, 35, 36, 37, 38 | |
| amine heterocycles | 20.8-20.10 | 39, 41, 42a,b,d,e,g,h, 44, 45, 47, 50 | |
| catch-up and review; course evaluations | |||
| ACS Organic Chemistry Exam, 1:30 PM | |||