CHEM 2541
ORGANIC CHEMISTRY 1
Spring 2008

TENTATIVE LECTURE SCHEDULE: Text book: "Organic Chemistry" by John McMurry (7th edition) - Recommended pages and problems

PAGE WILL BE UPDATED DAILY AFTER CLASS

Chapter 1. Structure and Binding.

Lecture 1 (01/23/08): Aufbau chart, Pauli exclusion principle, Hund's rule, electron configuration. Pages 1-6. Problems 1-2, 23
Lecture 2 (01/25/08): Octet rule, Lewis structures (electron-dot structures, line-bond structures), tetrahedral carbon, stereochemical representation of methane and ethane, covalent and ionic bonds, bond angles, sp3-hybridization. Pages 7-14, 19-20. Problems 3-9, 14, 24, 28, 31a
Lecture 3 (01/28/08): sp2/sp-hybridization, pi bond, sigma bond, skeletal/condensed structures. Pages 15-19, 22-24. Problems 10-13, 15-21, 25, 26, 27, 29, 31 b, c, d, 35, 56.

Chapter 2. Polar Covalent Bonds; Acids and Bases.
Lecture 4 (01/30/08): Electronegativity, dipole moments, formal charges, resonance. Pages 35-46. Problems 1-3, 5-6, 10, 20-21, 24-26, 32-34, 36, 41, 54-55.
Lecture 5 (02/01/08): Resonance, acids and bases. Pages 49-60. Problems 14-17, 36, 37, 38, 39, 40, 43-47, 53, 58.

Quiz 1: Monday, February 3, 2008

Chapter 3. Organic Compounds: Alkanes and Their Stereochemistry.
Lecture 6 (02/06/08): Functional Groups, Isomers, IUPAC Nomenclature. Pages 73-91. Problems 1b, 2, 3a, 3b, 6, 7-10, 22, 23, 25.
Lecture 7 (02/08/08): Conformations of Ethane, Propane and Butane. Pages 93-98. Problems 16a-c, 17, 42a-b.
Lecture 8 (02/11/08): Newman projection, sawhorse - structures, dash-and-wedges - structures. Problems: Use your modeling kit to build the structures mentioned in class.

Chapter 4.  Organic Compounds: Cycloalkanes and Their Stereochemistry. 
Lecuture 9 (02/13/08): Cycloalkanes, Nomenclature of cycloalkanes. Pages 107-109. Problems: 1, 2, 3, 25.
Lecture 10 (02/15/08): Ring strain, conformations of cycloalkanes, axial/equitorial bonds. Pages 113-124. Problems: modeling kit: Build a 1,2 disubstituted cyclopropane derivative and identify the trans and cis isomers. Build cyclohexane and identify chair, twist boat and boat conformations; axial and equatorial protons.

Quiz 2: Monday, February 18, 2008

Lecture 11 (02/20/08): Review Quiz 2.
Lecture 12 (02/22/08): Stability of cis and trans 1,2-disubsituted cylcohexanes. 1,3-diaxial interactions. Pages 124-128. Problems: 18, 19, 21, 22, 23, 29, 30.

Chapter 5: An Overview of Organic Reactions
Lecture 13 (02/25/08): Kinds of Organic Reactions. Reaction Mechanisms. Polar Reactions. Pages 137-139, 142-146, 149-152. Problems: 1, 4, 8, 9, 19-21, 30.

Midterm Exam 1: Wednesday, February 27, 2008, 11:00-11:50

Lecture 14 (02/29/08): Review Midterm Exam 1.

Chapter 6. Alkenes: Structure and Reactivity.
Lecture 15 (03/03/08): Alkenes. Molecular formula. Degree of Unsaturation. IUPAC Nomenclature - Part 1. Pages: 172-178. Problems 1-6, 20, 23-25.
Lecture 16 (03/05/08): IUPAC Nomenclature Part 2: cis/trans isomers, E/Z nomenclature, Priority rules, Methylen-, vinyl-, allyl-substituents. Electrophilic Addition of HBr. Markovnikov's rule. Pages: 179-193. Problems: 9-12, 26-32.
Lecture 17 (03/07/08): Mechanism of electrophilic addition. stability of carbocations, hydride/alkyl shift. Pages: 194-197, 200-202. Problems: 14-15, 19, 39, 40-42, 47-49 58.

Chapter 7.  Alkenes: Reactions and Synthesis.
Lecture 18 (03/10/08): Addition of halogens to alkenes, bromonium ion intermediates, halohydrin formation, stereoselectivity, regioselectivity. Pages 215-220. Problems: 3-6.
Lecture 19 (03/12/08): Oxymercuration and hydroboration. Pages: 220-226. Problems: 9-11, 21, 22.
Lecture 20 (03/14/08): Acid catalyzed addition of water to alkenes, oxidation of alkenes: epoxidation, hydroxylation. 233-239. Problems: 16-17.
Lecture 21 (03/24/08): Hydrogenation, ozonolysis. Pages: 227-233. Problems: 12, 13.
Chapter 8. Alkynes: An Introduction to Organic Synthesis.
IUPAC Nomenclature of alkynes. Preparation of Alkynes: Elimination reactions of dihalides. Pages 259-261. Problems: 1-2, 18.

Midterm Exam 2: Wednesday, March 26, 2008, 11:00-11:50

Lecture 22 (03/28/08): Reactions of Alkynes: Addition of HX and X2. Reduction of Alkynes. Alkyne Acidity. Alkylation of Acetylide Anions. Pages: 261-263, 268-270, 270-273. Problems: 3, 8, 9, 21
Lecture 23 (03/31/08): Hydration of Alkynes. Introduction to Organic Synthesis. Pages: 264-267, 274-278. Problems: 4-5, 6-7, 12-13, 23-26, 31-35.

Chapter 9. Stereochemistry.
Lecture 24 (04/02/08): Enantiomers, chirality, optical activity, rules for specifying configuration. Pages: 289-302. Problems: 1-5, 8-11, 31.
Lecture 25 (04/04/08): Levorotatory/dextrorotatory. Racemic mixtures. Amino acid nomenclature.
Lecture 26 (04/07/08): Diastereomers. Meso Compounds. Pages: 302-305. Problems: 12-16, 38, 39, 40, 41, 53.

Quiz 3: Monday, April 7, 2008

Lecture 27 (04/09/08): Fischer projection, separation of enantiomers.
Lecture 28 (04/14/08): Review: stereochemistry, isomers.
Chapter 10.  Organohalides.
IUPAC nomenclature of organohalides. Radical reactions - mechanistic aspects.
Pages: 332-339. Problems: 1-3, 17-19.
Lecture 29 (04/16/08): Bromination of cis and trans 2-butene. Comparison of electrophilic addition and allylic bromination. Resonance structures of allyl radicals. Pages: 339- 343. Problems: 5-7, 19-21, 24, 27-30.
Lecture 30 (04/18/08): Radical addition of HBr onto alkenes. Preparation of alkyl halides from alcohols. Grignard reagents. Gilman reagents. Pages: 344-348. Problems: 9-11, 22, 35-36.
Lecture 31 (04/21/08): Stille/Suzuki coupling, oxidation and reduction in organic chemistry. Pages: 348-350. Problems: 12-13, 31-33.

Midterm Exam 3: Wednesday, April 23, 2008, 11:00-11:50

Lecture 32 (04/25/08): Review Midterm Exam 3.

Chapter 11. Reactions of Alkyl Halides: Nucleophilic Substitutions and Elimination.
Lecture 33 (04/28/08): Sn2 reaction. Kinetics. Mechanism. Nucleophiles. Subtrates. Leaving groups. Solvents. Pages: 362-372. Problems: 1-7, 25-27, 28, 30.
Lecture 34 (04/30/08): Sn1 reaction. Characteristics of Sn1 reaction. Pages 372-381. Problems: 8, 9, 11, 12, 13, 36, 37.

Quiz 4: Monday, May 5, 2008

Lecture 35 (05/05/08): Zaitsev's rule. E2 reaction. E2 reaction and cyclohexane conformation. Pages 383-391. Problems: 15, 16, 17, 18.
Lecture 35 (05/07/08): E2 reaction
Chapter 12. Structure Determination: Mass Spectroscopy and Infrared Spectroscopy.
Handout IR spectroscopy. Problems: 7a, 7b, 8a, 30b, 30 c.
IR spectra examples

Final Exam. Monday, May 12, 2008, 10:00-11:55