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) Reactions → Alkenes and Alkynes → Degrees of Unsaturation |
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 | ||
| Martin Luther King Day -- no classes | ||||
| 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 | ||
| 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 | ||
|
Exam 1 review
Exam 1 is Thursday evening, Feb. 4, from 7-9 PM in Shoker Science Center |
||||
| spectroscopy and structural identification |
3.1; Ch. 12-13 Organic Chemistry Online: Spectroscopy II |
13.56; 14.36; 15.41, 57, 62 | ||
| bonding and MO theory |
1.5-1.10
Organic Chemistry Online: Structure & Bonding Brief Reviews: "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 Brief Reviews: "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: Reactions → Arenes Brief Reviews: "Aromaticity -- the 4n+2 rule" |
7.59, 79; 14.31, 33, 34, 38, 39, 40, 44
Organic Chemistry Online: Reactions → Arenes Problem sets: "Aromaticity" |
||
| UV/VIS spectroscopy & catch-up |
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: Reactions → Alkanes Brief Reviews: "Conformational Analysis" |
48, 58
Organic Chemistry Online: Reactions → Alkanes Problem sets: "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: Reactions → Alkanes Brief Reviews: "Conformational Analysis" |
55, 62, 65, 67, 68, 71, 72, 73, 5.95
Organic Chemistry Online: Reactions → Alkanes Problem sets: 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 |
3.41, 50, 53; 4.51, 54, 56, 58; 7.65, 75; 10.50, 73 |
||
| the Diels-Alder reaction |
7.12
Organic Chemistry Online: Reactions → Conjugated Dienes Brief Reviews: Cycloaddition Reactions |
61, 62, 64, 68, 69, 70, 71, 72, 74, 76, 77, 78 Organic Chemistry Online: Reactions → Conjugated Dienes Problem sets: "Cycloaddition Reactions;" all three synthesis problem sets |
||
| studying reactions: using rates and the structure of products |
8.10-8.12 Organic Chemistry Online: Reactions → Alkyl Halides; Substitution & Elimination Reactions Brief Reviews: "Substitution Reactions" |
44, 45, 46, 47, 48, 51, 52, 54, 55, 57, 58, 59, 60, 61
Organic Chemistry Online: Reactions → Alkyl Halides; Substitution & Elimination Reactions Problem Sets: "Substitution Reactions" |
||
| studying reactions: using rates and the structure of products |
9.5-9.7
Organic Chemistry Online: Reactions → Alkyl Halides; Substitution & Elimination Reactions Brief Reviews: "Elimination Reactions" |
33, 36, 37, 38, 41, 46, 48, 49, 52, 53, 54, 55, 56, 57
Organic Chemistry Online: Reactions → Alkyl Halides; Substitution & Elimination Reactions Problem Sets: "Elimination Reactions;" "Reactions II" |
||
|
Exam 2 review
Exam 2 is Thursday evening, Mar. 4, from 7-9 PM in Shoker Science Center |
||||
| Spring Break -- no classes | ||||
| 100-point quiz over material covered on Exam 2 | ||||
| spectroscopy and structural identification |
Spectroscopy II problem set on Organic Chemistry Online CD: [CD]:\OCOL_HTM\OCOL\OCOL.HTM click on "Spectroscopy II" |
Pay special attention to problems 80-100 | ||
|
conformation, strain and cyclic compounds conformations of cyclohexane |
2.11-2.14
Organic Chemistry Online: Reactions → Alkanes → Brief Reviews: "Conformational Analysis" Organic Chemistry Online: Reactions → Alkanes Problem sets: Conformational Stability" See Dublin University's Conformational Analysis website, and Chair/boat cyclohexane |
48, 55, 58, 62, 65, 67, 68, 71, 72, 73, 5.95
Organic Chemistry Online: Reactions → Alkanes Problem sets: "Conformational Stability" See Newman projections See also Dublin University's Conformational Analysis website, and Chair/boat cyclohexane |
||
| the Diels-Alder reaction and molecular orbitals |
7.8, 7.12
Organic Chemistry Online: Structure & Bonding → Brief Reviews: "Ionic, Polar and Covalent Bonds;" "Atomic & Molecular Orbitals" constructing MOs for conjugated molecules Organic Chemistry Online: Reactions → Conjugated Dienes Brief Reviews: Cycloaddition Reactions see also What are anti-bonding orbitals? |
59, 61, 62, 64, 68, 69, 70, 71, 72, 74, 76, 77, 78, 79
Organic Chemistry Online: Reactions → Conjugated Dienes Problem sets: "Cycloaddition Reactions;" all three synthesis problem sets |
||
| Substitution & elimination reactions | Chapters 8 and 9 animated reaction mechanisms | 33, 36, 37, 38, 41, 44, 45, 46, 47, 48, 49, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61 | ||
| Exam review | ||||
| Aromaticity and aromatic compounds |
14.1-14.7
Organic Chemistry Online: Reactions → Arenes Brief Reviews: "Aromaticity -- the 4n+2 rule" |
31, 33, 34, 38, 39, 40, 44
Organic Chemistry Online: Reactions → Arenes Problem sets: "Aromaticity" |
||
| reactivity of substituted benzenes |
15.1-15.3; skim 15.9-15.14
Organic Chemistry Online: Reactions → Arenes Brief Review: "Electrophilic Aromatic Substitution" |
34, 35, 38, 40, 44, 55
Organic Chemistry Online: Reactions → Arenes Problem Sets: "Electrophilic Aromatic Substitution" |
||
| Good Friday -- no classes | ||||
| Easter Monday -- no classes | ||||
|
Engagement Day -- service projects Because we are behind, we will have class on substituent effects and their use in synthesis |
15.4-15.14
Organic Chemistry Online: Reactions → Arenes Brief Review: "Reactions of Aryl Side Chains" |
37, 39, 42, 43, 46, 48, 51, 52, 53, 56, 64
Organic Chemistry Online: Reactions → Arenes Problem Sets: "More Arene Reactions;" "Multistep Synthesis" |
||
|
Exam review
Exam is Thursday evening, April 8, from 7-9 PM in Shoker Science Center spend the weekend reviewing Chapters 16.1 through 17.10 Organic Chemistry Online: Reactions → Aldehydes & Ketones (except "Conjugate Addition") Organic Chemistry Online: Reactions → Carboxylic Acids Organic Chemistry Online: Reactions → Acyl Derivatives |
||||
| 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 | ||
| carbonyl reactivity: α,β-unsaturated carbonyls and keto-enol tautomerism |
17.16-17.18, 18.1-18.3
Organic Chemistry Onine: Reactions → Aldehydes & Ketones Brief Reviews: "Conjugate Addition Reactions of Aldehydes & Ketones" |
17.60, 62, 67, 80, 81, 82, 83, 84; 18.51, 52, 56, 61, 77
Organic Chemistry Onine: Reactions → Aldehydes & Ketones Problem Sets: "Synthesis I" & "Synthesis II" |
||
| reactions at the α-carbon: alkylation & acylation |
18.4-18.10
Organic Chemistry Online: Reactions → Carbonyl α-Substitution Brief Reviews: "Simple Substitution Reactions" |
58, 63, 64, 73, 74, 78, 80
Organic Chemistry Online: Reactions → Carbonyl α-Substitution Problem Sets: "alpha-Substitution Reactions" I & II |
||
| Named reactions: Michael, Aldol, Claisen, etc |
18.11-18.17
Organic Chemistry Online: Reactions → Carbonyl Condensation Reactions Brief Reviews: all topics |
53, 57, 65, 67, 68, 69, 70, 71, 76, 83, 84
Organic Chemistry Online: Reactions → Carbonyl α-Substitution Problem Sets: all problem sets |
||
| putting it all together: malonic & acetoacetic ester syntheses |
18.18-18.22
Organic Chemistry Online: Reactions → Carbonyl α-Substitution Brief Reviews: "The Malonic Ester Synthesis" & "The Acetoacetic Ester Synthesis" |
48, 49, 50, 54, 55, 59, 60, 62, 66, 72, 75, 79, 81, 82, 85
Organic Chemistry Online: Reactions → Carbonyl α-Substitution Problem Sets: all |
||
| Exam review; the examination is Thursday evening from 7-10 PM | ||||
| amine chemistry: nomenclature, reactions and synthesis |
20.1-20.7
Organic Chemistry Online: Reactions → Aliphatic & Aromatic Amines Brief Reviews: "Nomenclature;" "Reactions of Amines;" "Reactions that Yield Amines" |
26, 27a,c,f, 28, 30, 33, 40, 42c,f,i, 43, 46, 48, 49
Organic Chemistry Online: Reactions → Aliphatic & Aromatic Amines Problem Sets: "Nomenclature;" "Amines, Reactions;" "Amines, Multistep Synthesis" |
||
| amine heterocycles | amine heterocycles | 20.8-20.10 |
27b,d,e,g,h,i, 29, 31, 32, 34, 35, 36, 37, 38
Extra practice: 39, 41, 42a,b,d,e,g,h, 44, 45, 47, 50 |
|
| catch-up and review; course evaluations | ||||
| ACS Organic Chemistry Exam, 8:00 AM | ||||