CHEM 222 Lect.

51 and 03 Winter 2018

Lec. Lec.3 Topics Pages in Suggested problems Chapters in Coursepack
51 Coursepack
1 Jan. Jan. Syllabus, Introduction, Index of
8th 9th hydrogen deficiency (Figures needed,
Moodle week 1)
2 Jan. Jan. Mass Spectrometry: Fragmentation 3-12 Bruice 13.30, 13.34, 13.39 Organic Chemistry (4th ed., Bruice)
8th 11th and isotope; IR: Introduction Sections 13.1-13.3,13.6-7
3 Jan. Jan. IR: fingerprint and characteristic 12-20 Bruice 13.32 fgjkl, 13.33, Organic Chemistry (4th ed., Bruice)
15th 16th bands (Figures needed, Moodle week 13.41a, 13.44-45ac, 13.47, Sections 13.8-15.
2) 13.49, 13.50-51, 13.54a
4 Jan. Jan. NMR: spin state, equivalent proton, 25-31 Bruice14.41, 14.43 Organic Chemistry (4th ed., Bruice)
15th 18th chemical shift BONUS TEST Sections 14.1-14.7
5 Jan. Jan. NMR: integration and splitting 31-37 Bruice 14.44, 14.46a-g, 13.48-
Organic Chemistry (4th ed., Bruice)
22th 23th (Figures needed, Moodle week 3) 49, 14.52, 14.54-55, 14.60,
Sections 14.8-14.11
14.64, 14.67
6 Jan. Jan. 13
C NMR Structure determination: 43-45 Bruice 14.53, 14.57, 14.59, Organic Chemistry (4th ed., Bruice)
22th 25th problem solving 14.69bcd, 14.71 Sections 14.18
7 Jan. Jan. Conjugated diene: conjugation and 59-62, 68-70 McMurry 14.21, 14.39, 14.40, Organic Chemistry (8th ed., McMurray)
29th 30th UV-Vis spectroscopy (Figures 14.43 Sections 14.1 and 14.7-14.8
needed, Moodle week 4)
8 Jan. Feb. Conjugated diene: kinetic vs 62-64 McMurry 14.22abcd, 14.23-25, Organic Chemistry (8th ed., McMurray)
29th 1st thermodynamic control. 14.44, 14.51 Sections 14.2-14.3
9 Feb. Feb. TEST 1 Alcohols: acidity and basicity 319- 323 Solomons 11.25-26abcde Organic Chemistry (10th ed., Solomons &
5th 6th Fryhle) Sections 11.1A-11.3
10 Feb. Feb. Alcohols: addition, substitution. 323-328 Solomons 11.27-30a, 11.32 Organic Chemistry (10th ed., Solomons &
5th 8th Fryhle) Sections 11.4-11.10,
11 Feb. Feb. Alcohols: oxidation, elimination, 331, 41-42, Solomons 11.34-35, 12.13abde, Organic Chemistry (10th ed., Solomons &
12th 13th protection and spectroscopy. (Figures 342-349, 351- 12.15a, 12.16-17abc Fryhle) Sections 12.2-12.4, 12.7B, 12.8AB,
needed, Moodle week 6) 352, 356 12.9 and
Organic Chemistry (4th ed., Bruice)
Sections 14.15-16
12 Feb. Feb. Ether and epoxide: synthesis and 320-323, 329- Solomons 11.26fghij,11.38- Organic Chemistry (10th ed., Solomons &
12th 15th reaction 331, 332-337, 40defij, 11.41ab, 11.42-43, Fryhle) Sections 11.1B-11.3, 11.11-11.15,
351 11.47-48 12.7B
13 Feb. Feb. Benzene: nomenclature and 76-86 McMurry 15.18-22, 15.29, Organic Chemistry (8th ed., McMurray)
26th 27th aromaticity 15.33-34, 15.37 Sections 15.1-15.7
14 Feb. Mar. Diels Alder reaction (Figures needed, 64-67 McMurry 14.26-35, 14.48 Organic Chemistry (8th ed., McMurray)
26th 1st Moodle week 7) Sections 14.4-14.5
CHEM 222 Lect.51 and 03 Winter 2018

15 Mar. Mar. Electrophilic aromatic substitution: 93-96 McMurry 16.28-30, 16.32-33, Organic Chemistry (8th ed., McMurray)
5th 6th mechanism 16.37-38, 16.40, 16.43, 16.49- Sections 16.1-16.2
53
16 Mar. Mar. EAS: activation and directing effect 99-105, 109- McMurry 16.31a-g, 16.34- Organic Chemistry (8th ed., McMurray)
5th 8th (Figures needed, Moodle week 8) 112 36abc, 16.45-47abc, 16.48, Sections 16.4-16.6
16.54-55a, 16.68-69
17 Mar. Mar. EAS: Friedel-Craft reactions. 97-99, 107- Brown 16.15-16a-h Organic Chemistry (8th ed., McMurray)
12th 13th Reactions on substituents (Figures 111, 373-375 Sections 16.9-16.11 Organic Chemistry (10th
needed, Moodle week 9) TEST 2 ed., Solomons & Fryhle) Sections 20.6 A-B-
20.7
18 Mar. Mar. Carbonyl: introduction. 121-129 Brown 16.19-22 Organic Chemistry (3rd ed., Brown & Foote)
12th 15th Sections 16.1-16.5
19 Mar. Mar. Aldehyde and Ketone: nucleophilic 128-134, Brown 16.31, 16.36 Organic Chemistry (3rd ed., Brown & Foote)
19th 20th addition, reduction, Grignard reagent 349-355 Sections 16.5-16.6, Organic Chemistry (10th
ed., Solomons & Fryhle) Sections 12.6-12.8
20 Mar. Mar. Aldehyde and Ketone: hydration, 137-145 Brown 16.43 Organic Chemistry (3rd ed., Brown & Foote)
19th 22th acetal Sections 16.8
21 Mar. Mar. Aldehyde and Ketone: imine and 147-150, Brown 16.24-25, 16.54a-c,e-j, Organic Chemistry (3rd ed., Brown & Foote)
26th 27th enamine formation 158-165 16.55a-c,e-j, 16.56-57, 16.60- Sections 16.10,16.13
61, 17.7a-d, 17.8-9, 17.17,
17.25-28
22 Mar. Mar. Aldehyde and Ketone: Wittig 134-136, Brown 17.18ad, 17.19bcd, Organic Chemistry (3rd ed., Brown & Foote)
26th 29th reactions. Carboxylic acids: 183-192 17.20a-e,g, 17.21-23, 17.32- Sections 16.7 Organic Chemistry (3rd ed.,
nomenclature, acidity 33, 17.35 Brown & Foote) Sections 17.1-17.4
23 Apr. Apr. Lab Exam Carboxylic acids: 192-196 18.13-14a,b-f, i, 18.17-21, Organic Chemistry (3rd ed., Brown & Foote)
9th 3th formation and hydration (Figures 18.24abc, 18.25-30, 18.32-33, Sections 17.5-17.6
needed, Moodle week 12) 18.35, 18.41, 18.45, 18.47-48
24 Apr. Apr. Carboxylic acid derivatives: Reaction, 196-203, Brown 16.50 Organic Chemistry (3rd ed., Brown & Foote)
9th 5th Hydrolysis, nucleophilic acyl 217-252 Sections 17.7-17.8,18.1-18.11
substitution
25 Apr. Apr. Enols and enolates: tautomerization, 151-158 20.19abcqst, 20.20abei, 20.22a- Organic Chemistry (3rd ed., Brown & Foote)
16th 10th bromination and alkylation e, 20.23a, 20.24a, 20.25abc, f- Sections 16.11-16.12
m, 20.26, 20.30a-d, g 20.31a-j,
m
26 Apr. Apr. Enols and enolates: Aldol and Claisen 269-276, McMurry 16.28-30, 16.32-33, Organic Chemistry (3rd ed., Brown & Foote)
16th 12th condensation. 279-282, 16.37-38, 16.40, 16.43, 16.49- Sections 19.1, 19.3A, Organic Chemistry
Amine: Basicity and alkylation 361-365, 53 (10th ed., Solomons & Fryhle) Sections 20.1-
367-370 20.3 A-E, 20.4 A-D