ACPHS Home | Organic Chemistry I | Organic Chemistry II | Lecture | Laboratory
| Instructor Martha A. Hass, PhD Office: OB 118 email: martha.hass@acp.edu Phone: (518) 694-7238 |
Organic Chemistry II Spring 2015 Lecture Syllabus |
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Textbook Organic Chemistry, 8th Edition John McMurry (HYBRID) (ISBN: 0-840-05444-0) Access the eBook and OWL problems Virtual Textbook of Organic Chemistry William Reusch, PhD (Relevant Topics and Practice Problems) |
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Week |
Outlines |
Chapter Section(s) * available in print or eBook on OWL |
(Recordings for lectures
and review sessions are available by clicking on
this link. For some lectures/reviews, recordings are
not available)
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Homework Problems *additional problems available in OWL |
Relevant
Old Exam Questions |
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Chapter 17 (updated 2-14-14) |
17.1-17.2 2.12 |
Introduction Definition and Structure of Alcohols and Phenols ___________________________________________________ Physical Properties of Alcohols and Phenols |
Problem Set #1 17.1, 17.2, 17.5, 17.25, 17.28, 17.29 (Solutions) |
S2011 Exam 2: 8, 15, 17, 24 S2012 Exam 2: 15, 19 S2013 Exam 1: 4, 21, 22, 25 Exam 2: 24 |
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Jan.26-30 |
Oxidation Summary |
8.7-8.8, 10.8, 17.3, 17.7 |
Physical Properties of Alcohols and Phenols (Lecture recording for 1/27/14 not available) Preparation and Reactions of Alcohols: Oxidations Preparation and Reactions of Alcohols: Oxidative Cleavage Reactions |
Problem Set # 2 8.13, 8.26(d,f), 17.41, 17.42, 18.28, 18.30c, 18.35, 18.36 (Solutions) Problem Set # 3 8.14, 8.16, 8.28a, 8.35 (e,f), 8.45, 17.14, 10.12, 10.13, 17.34c, 17.62 (Solutions) |
S2011 Exam 2: 1, 7, 9 S2012 Exam 2: 1, 14 Exam 3: 1, 8, 13, 20, 22, 24 S2013 Exam 1: 3, 8, 12, 14, 15, 19 Exam 3: 2, 7, 12 |
Feb. 2-6
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Review of Substitutions and Eliminations Stereochemistry Review |
8.1, 11.7, 11.10 17.3, 17.6 |
Oxidative Cleavage: Formation of Diols and Carbonyls Oxidative Cleavage of Alkene: Formation of Epoxides _______________________________________ Reactions of Alcohols: Dehydration of Alcohols (E1 and E2) Formation of Alkenes and Dienes |
Problem Set #4 10.8, 10.21 (a,b,d), 10.39, 11.45, 11.51, 11.58, 17.34 (a,b), 17.40, 17.55, 17.65 (Solutions) |
S2011 Exam 1: 21 Exam 3: 13, 18 S2012 Exam 1: 9 Exam 2: 4 S2013 Exam 1: 1 |
Feb.9-13 |
Chapter 18 Review of Thermodynamics and Kinetics |
10.5, 11.2-11.5, 17.6 5.1-5.7 18.1-18.2 |
Reactions of Alcohols: Dehydration of Alcohols (E1 and E2) Formation of Alkenes and Dienes Preparation and Reactions of Alcohols: SN1 and SN2 Reactions Conversion of Alcohols to Alkyl Halides and Tosylates Conversion of Alcohols to Ethers via SN1 and SN2 Reactions |
Problem Set #6 11.4, 11.12, 11.27, 11.31, 11.33, 11.41, 11.42, 11.45, 11.47, 11.57 (Solutions) Problem Set #7 18.1, 18.5, 18.6, 18.23, 18.24, 18.25 (Solutions) |
S2011 Exam 2: 13, 16, 22 Exam 3: 10, 21 S2012 Exam 1: 6 Exam 2: 23 S2013 Exam 1: 2,5, 6, 7, 11, 13, 17, 23, 24 |
Feb.16-20 |
Review of Additions Chapter 14 Diene Structures Resonance Review Hybridization Review |
7.7-7.8 8.4-8.5, 8.12-8.13 17.3 14.1 14.2 14.3 14.4-14.5 |
Preparation of Alcohols: Markovnikov and Anti-Markovnikov Additions Types of Dienes Reactions of Dienes: Electrophilic Addition Thermodynamic and Kinetic Control in the Electrophilic Addition of Conjugated Dienes |
Problem Set #5 8.7, 8.8, 8.9, 8.10, 8.27e, 8.28 (c,d), 17.6 8.14, 8.28b, 8.32c (Solutions) Problem Set #8 14.2, 14.3, 14.20, 14.21 (Solutions) Problem Set #9 14.7, 14.23, 14.22 (a, c, e) (Solutions) |
S2011 Exam 3: 12, 16 S2012 Exam 2: 9 Exam 3: 9, 16 S2011 Exam 2: 2, 10, 11, 20 S2013 Exam 1: 2,5, S2012 Exam 1: 18, 19, 21, 23 S2012 Exam 1: 7, 11, 16, 20, 25 |
| Exam 1 Wednesday, February 18, 2015 Time: 7:00-9:00pm Room: SC 201/202 (back to top) |
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Feb.23-27 |
Chapter 14 Resonance Review |
14.4-14.5 |
Reactions of Dienes: Diels Alder Reaction Resonance and Substituent Effects Substituent Effects in the Diels Alder Reaction |
Problem Set #10 14.8, 14.9, 14.26, 14.27, 14.28, 14.32, 14.35, 17.51 (Solutions) |
S2012 Exam 1: 7, 11, 16, 20, 25 |
Mar. 2-6 |
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15.1; 15.2 15.3, 15.6 15.4, 15.5 2.7-2.11 |
Structure and Nomenclature of Benzene and Substituted Benzenes Criteria for Aromaticity; Polycyclic Aromatics Aromatic Ions; Heteroaromatics ________________________ Acids and Bases Consequences of Aromaticity Other Consequences of Aromaticity |
Problem Set #11 15.1, 15.2, 15.3, 15.18, 15.19, 15.20, 15.21 (Solutions) _____________ Problem Set #12 15.5, 15.10, 15.11, 15.12, 15.25, 15.31, 15.35, 15.38, 15.42, 15.43, 15.44 (Solutions) |
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Mar.9-13
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Chapter 16 |
20.2-20.4 24.2-24.5 |
Substituent Effects on the pKa of Ionizable Substitutents on Benzene (Benzoic Acids, Phenols, Anilines and Sulfonamides) Sigma Values |
Problem Set #13 16.40, 16.64, 16.71, 16.73, 16.74, 17.52, 17.5 (Solutions) |
S2011 Exam 2: 19 S2012 Exam 1: 22, 24 |
| SPRING
BREAK No Classes March 16-20, 2015 |
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Mar.23-27 |
Summary of Substituent Effects Chapter 16 |
16.1-16.3 16.4-16.6 |
Substituent Effects on the Electrophilic Addition of Styrenes Substituent Effects on the Hydrolysis of Benzoate Esters Electrophilic Aromatic Substitutions Substituent Effects on Electrophilic Aromatic Substitutions |
Problem Set #14 16.1, 16.3, 16.5, 16.6, 16.7, 16.8, 16.9, 16.12, 16.14, 16.39, 16.43, 16.48, 16.50, 16.52, 16.65 (Solutions) |
2011, Exam 2: 4, 10, 12, 21 2012, Exam 2: 8, 12, 20, 21 2013, Exam 2: 7, 9, 12, 22 ______________ 2011, Exam 1: 5,9,13,14, 17,20,23,25 2012, Exam 2: 2,5,10,11,17 2013, Exam 2: 12, 20, 25 2013, Exam 3: 4,5,10, 21 |
EXAM 2
Wednesday, March 25, 2015
Time:
7:00-9:00pm SC201/202 (back to top) |
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Mar. 30-Apr 3 |
Summary of Substituent Effects Chapter 16 |
16.7, 16.8 ___________________ 16.9-16.10 |
Substituent Effects on Electrophilic Aromatic Substitutions _________________________________________________ Benzyne Reaction Nucleophilic Aromatic Substitutions _________________________________________________ Oxidations of Substituents on Benzene Reductions of Substituents on Benzene |
Problem Set #15 16.16, 16.17, 16.61, 16.62, 16.63 (Solutions) __________________ Problem Set # 16 16.18, 16.20, 16.47, 16.48 (a,c), 16.51, 16.58, 16.68, 16.69 (Solutions) |
2011, Exam 1: 12, 15, 16 2012, Exam 2: 1,6,7 2013, Exam 3: 6, 14, 19, 23 ___________________ 2011, Exam 2: 5,6,14,23,25 2012, Exam 2: 3, 14, 16, 22,24,25 2013, Exam 3: 15, 25 |
Apr 6-10 |
Overview of Carbonyls ____________ Chapter 19 |
17.4-17.5 Preview of Carbonyls pp. 712-720 21.6 _________________ 10.6-10.7 19.7 22.1, 22.5-22.6 |
Carbonyl-Containing Functional Groups: Structure and General Reactivity _____________________________________________________ Preparation of Aldehydes and Ketones Organometallic Reagents Reaction of Organometallics with Carbonyls |
Problem Set #17 2, 3 (pg. 721), 17.7, 17.8, 17.31, 17.43 (Solutions) |
2012, Exam 3: 1,8,20, 22 2013, Exam 1: 22 2013, Exam 3: 2,7,12,24 |
Apr.13-19 |
Chapter 19 |
5.11 19.4-19.81 |
Prochirality and Stereochemistry of Nucleophilic Acyl Additions Reactions of Carbonyls Nucleophilic Acyl Additions: Aldehydes and Ketones |
Problem Set # 18 19.9,19.10,19.18,19.20, 19.40 (b,c,d,e,f,h), 19.61, 19.75, 21.68 (Solutions) _________________ Problem Set # 20 17.9, 17.10, 17.30, 17.32, 17.54, 19.34d, 19.36, 19.41, 5.23a, 5.24, 5.59 (Solutions) |
2011, Exam 3: 2 2012, Exam 3: 2,15,23 2013, Exam 3: 20 _____________________ 2011, Exam 2: 3 2011, Exam 3: 5,6,8,20,23 2012, Exam 2: 13 2012, Exam 3: 3, 11 2013, Exam 3: 9, 13, 18, 22 |
Apr.20-24 |
Chapter 22 Chapter 23 |
Reactions of Carbonyls Nucleophilic Acyl Additions: Aldehydes and Ketones Generation of Enols and Enolates Substitution Reactions |
Problem Set # 19 10.11, 10.34, 10.36, 22.1, 22.20, 22.22, 22.24, 22.34, 22.35, 22.46, 22.48, 22.58 (Solutions) Problem Set # 23 19.22, 23.16, 23.17, 23.41, 23.45 (Solutions) |
2011, Exam 2: 3 2011, Exam 3: 4, 5,6,8,14,23 2012, Exam 2: 13 2012, Exam 3: 2,3,6,10,12,15,25 2013, Exam 3: 9, 13, 18, 20 |
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| EXAM 3 Tuesday, April 21, 2015 Time: 7:00-9:00pm Room: SC 201/202 (back to top) |
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Apr. 27- May 1 |
Chapter 23 Chapter 21 |
23.1-23.3, 23.5-23.9 22.7 19.13 23.10 21.3, 21.6 21.4, 21.5, 21.7 |
Condensation Reactions: Aldol, Mixed Aldol and Conjugate Addition Reactions to Unsaturated Aldehydes and Ketones Michael Addition Reactions Nucleophilic Acyl Substitutions: Other Carboxylic Acid Derivatives Claisen Condensations; Intramolecular Condensations |
Problem Set # 24 23.1, 23.3, 23.5, 23.8, 23.10, 23.11, 23.14, 23.30, 23.35 (Solutions) Problem Set # 22 20.33, 20.36, 20.37, 20.52; 21.5, 21.39 (Solutions) Problem Set # 21 21.18, 21.19, 21.35, 21.40, 21.41 (Solutions) |
2011, Exam 2: 4,12,18,21 2011, Exam 3: 2,3,9,15,17,22,25 2012, Exam 2: 12,21 2012, Exam 3: 4,5,7,11,14,17,19,21,23 2013, Exam 2: 7 2013, Exam 3: 8 |
FINAL EXAM TBD All Chapters Above, All Lab Experiments |
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