LECTURE OUTLINE/RECOMMENDED ASSIGNMENTS
CHEM 2541: ORGANIC CHEMISTRY I LECTURE, Summer 2010

 

This web page will not be updated. All dates are tentative.

The page and problem numbers refer to the 5th edition of Brown & Foote. The page and problem numbers for the 4th edition are in parenthesis.

 

1 - Covalent Bonding and Shapes of Molecules.

05/17/10: Electron Configuration - Aufbau Principle, Pauli Exclusion Principle, Hund's Rule. Pages 1-4 (4th 1-4).Problems 1.1, 1.20-21. (4th 1.1, 1.19-1.20)

05/17/10: Lewis Dot Structures. - Valence electrons, valence shell. Octet Rule. Type of Bonds. Polarity of Bonds. Pages 5-11. (4th 5-11). Problems: 1.2-5, 1.23-24, 1.26. (4th 1.2-5, 1.22-23, 1.25).

05/19/10: Lewis Structures of molecules and polyatomic Ions. Formal charge. Pages 11-15 (top), 16 (4th 11-15). Problems: 1.6-1.7, 1.27-32 (4th 1.6-1.7, 1.26-1.31). Internet: A B

05/19/10: Functional Groups - Examples: alcohol, amine, aldehyde, ketone, carboxylic acid, - ester, - amide. Quiz 1. Pages: 18-22 (4th 18-23). Problems 1.8-12 (4th 1.8-12). Practice Problems for class discussion on 01/29/10.

05/21/10: Discussion of functional group handout. Shapes of Organic Molecules. Hybridization, Types of bonds. Pages 22-24 (4th 23-26). Problems 1.13a, 1.13c, 1.38, 1.39, 1.41, 1.42a, 1.48. (4th 1.13 a, 1.13c, 1.37, 1.38, 1.40, 1.41a, 1.47).

05/21/10: Shapes of atomic, sigma and pi-bonding orbitals. Bond lenghts/strengths. Resonance. Pages: 40 (Table 1.10), 41-43, 50 (Table 1.11). (4th 45 (Table 1.10), 46 (Table 1.11) 29-31). Problems: 1.15-17, 1.52, 1.56-1.57. (4th 1.15-1.16, 1.18, 1.51, 1.55-1.56)

05/24/10:  Resonance - Estimating realtive Importance of Contributing Structures. Quiz 2 Pages 43-45 (4th 32-34). Problems: 1.18, 1.54 (4th 1.17, 1.53).

2 - Alkanes and Cycloalkanes.

05/24/10: Structure of Alkanes. Molecular Formula, Line-angle formula (also called skeletal formula), (Condensed) Structural Formula. Constitutional Isomers/Stereoisomers (Definition). Pages: 61-63. (4th 56-59). Problems 2.1, 2.16-2.17, 2.20-2.23 (4th 2.1, 2.16-2.17, 2.20-2.23)

05/26/09: IUPAC Nomenclature of Alkanes. Common names of Alkanes. Classification of Carbon atoms. Pages: 65-68, 70-71 (4th 61-64, 67-68). Problems: 2.3, 2.27 a-f, 2.28 a-f (4th 2.3, 2.27 a-f, 2.28 a-f).

05/26/10: IUPAC names of Cycloalkanes. Quiz 3 Pages 73-74 (68-69). Problems: 2.5, 2.28 g,h. (4th 2.5, 2.28 g, h)

05/28/10 Conformations of ethane and butane. Newman Projections. Pages: 73-75 (4th 70-72). Problems: .8a, 2.33, 2.34a,b. (4th 2.8a, 2.33, 2.34a,b. More Newman projection problems


05/28/10: Energy profile of butane as function of dihedral angle. Conformations of Cyclopropane, -butane, -hexane. Chair conformation of cyclohexane. Pages: 76-84 (4th 72-81). Problems: 2.8b, 2.34c, 2.9, 2.10 (4th 2.8b, 2.34c, 2.9, 2.10).

06/02/10: Conformations of disubstituted Cyclohexanes. Models
. Cis/Trans Isomerism in Cycloalkanes. Pages: 85-90 (4th 82-89). Problems: 2.12-2.14 (4th 2.12-2.14)

06/02/10: Review isomerism. Cis/trans isomers examples. Relative stability of substituted cycloalkanes.Isomer Problems
. (Problem 2, only - In this case "configurational isomers" has the same meaning as "cis/trans isomers")

06/04/10: Midterm Exam 1 

 

3 - Stereochemistry and Chirality

06/04/10: Stereoisomerism. Chirality - The Handedness of Molecules. Quiz 4. Pages: 112-116 (4th 111-116 ). Problems: 3.1.

06/07/10: Naming Chiral Centers - The R,S System. Pages: 117-119 (4th 116-120). Problems:  3.2-3. More practice problems (skip #4, 5, 8) Even more practice problems (carbon grey, nitrogen dark blue, hydrogen turqoise, oxygen red).

06/07/10: (A)cyclic Molecules with Two or More Chiral Centers: 120-124 (4th 120-124) (skip Fischer Projection), 125-128 (4th 125-128). Problems: 3.4-5, 3.7-8. More practice problems (skip #4, 5, 6, 10)

 

4 - Acids and Bases

06/09/10: Bronsted-Lowry Acids and Bases. Relative Strength of Acids and Bases, Position of the Equilibrium. Pages 150 (first 3 paragraphs, we will talk about those curved arrows later, so skip it), 156-161 (4th 152-155, 158-163). Problems: 4.1, 4.6 (no calculation)

06/09/10: Molecular Structure and Acidity. Pages 165-171 (4th 165-170). Practice problems Even more practice problems

5 - Alkenes

06/11/10: Index of hydrogen deficiency. cis/trans alkenes. Nomenclature of simple acyclic alkenes. Pages 185-189. (4th 184-189). Problems: 5.1-5.4.

06/14/10: E/Z Nomenclature. Nomenclature Cycloalkenes. Pages: 189-190. (4th 189-190). Problems: 5.5, 5.6. More Practice problems

06/14/10: Midterm Exam 2

 

 6 - Reactions of Alkenes

06/16/10: Additions of Hydrogen Halides. Pages: 208-214 (4th 209-216). Problems: 6.1-3

06/16/10: Carbocation rearrangements. Pages: 216-218 . A few Carbocation Rearrangement Problems

06/18/10: Addition of Bromine or Chlorine. Pages: 219-221 (4th 221-223) Problem: 6.7

06/18/10: Addition of HOCl or HOBr. Pages: 221-223 . (4th 223-225). Problem: 6.8. Addition of water: a) Acid catalyzed. Pages: 214-216 (4th 216-218). Problems: 6.4, 6.5, 6.6.

06/18/10: Addition of water: b) oxymercuration-reduction and c) hydroboration-oxidation. Quiz 5 Pages: 223-229 (4th 226-232).

06/21/10: Oxidation Reactions of Alkenes (You are not required to know the mechanism). Reduction of Alkenes - Hydrogenation. Pages: 232-236 (4th 235-239). Problems: 6.12

 

7 - Alkynes

06/21/10: IUPAC Nomenclature of Alkynes. Acidity of Alkynes. Alkylation of Alkynes. Hydration of Alkynes. Catalytic Reduction. Pages: 257, 259-260, 265-270. (4th 265, 267-269, 274-280. Problems: 7.1, 7.4, 7.5.

06/21/10: Dissolving Metal Reduction. Organic Synthesis. Pages: 271-275 (4th 281-284). Problems: 7.6, 7.14, 7.17. A few Synthesis Problems

 

8 - Haloalkanes, Halogenation, and Radical Reactions

06/23/10: IUPAC Nomenclature. Preparation of Haloalkanes - Radical Halogenation of Alkanes. Pages: 287-287, 296-298 (4th 293-294, 304-306).

06/23/10: Radical Halogenation of Alkenes. Allylic Halogenation. Radical Addition of HBr to Alkenes. Pages: 303-307, 310-312.

9 - Nucleophilic Substitution and beta-Elimination

06/23/10: Nucleophilic Substitution: Pages: 321-334, 340-344 (4th 329-332, 334-337, 341-354) Problems 9.1-9.5, 9.11, 9.13.

06/25/10: Beta-elimination: Pages 344-353 (4th 354-364) 9.6-9.7, 9.37-9.39.A few Substitution/Elimination Problems
(Answers: www.d.umn.edu/~pgrundt/2541/Problem_Sets/Sub_Eli_Answers.pdf)

 

10 - Alcohols

06/25/10: Nomenclature of Alcohols. Physical Properties - hydrogen bonding. Acidity/Basicity of Alcohols. Pages: 375-379 (4th 385-389), 381-382 (4th 392-393). Problems: 10.1-3, 10.14, 10.16.

06/25/10 Reaction of Alcohols with active metals. Quiz 6
Page 382 (4th 393). Problem 10.6.

06/28/10: Conversion to Haloalkanes/Sulfonates. Pages: 383-388 (4th 394-400). Problems: 10.7, 10.31 c, d, h.

06/28/10: Acid-Catalyzed Dehydration. Oxidation Reactions. Pages: 389-393, 396-398 . (4th 401-406, 409-413). Problem: 10.8-9, 10.31 a, e

06/28/10: Midterm Exam 3