CHEMISTRY 2541, Fall Semester 2015

RECOMMENDED READING AND PROBLEM ASSIGNMENTS 

"Organic Chemistry", 5th edition (2009) or 6th edition (2011) by Brown & Foote

Answers to the recommended problems can be found in:
"Brown Organic Chemistry student solutions manual/study guide" (e-book or hard copy)

Chapter 1. COVALENT BONDING AND SHAPES OF MOLECULES
1.1. Electronic Structure of Atoms
1.2. Lewis Model of Bonding
How To: Draw Lewis Structures from Condensed Structural Formulas
1.3. Functional Groups
1.4. Bond Angles and Shapes of Molecules (VSEPR)
1.5. Polar and Nonpolar Molecules (molecular dipole moments)
1.6. Quantum or Wave Mechanics )introduction, shapes of s and p orbitals)
1.7. A Combined Valence Bond and Molecular Orbital Theory Approach to Covalent Bonding (MO and orbital hybridization)
1.8. Resonance (rules for writing ontributing structures)
How To: Draw Curved Arrows and Push Electrons in Creating Contributing Structures
1.10. Bond Lengths and Bond Strengths in Alkanes, Alkenes, and Alkynes

Problems and Examples: 1.1-1.20, 1.22-1.25, 1.27-1.28, 1.51-1.54

Chapter 2. ALKANES AND CYCLOALKANES
2.1. The Structure of Alkanes
2.2. Constitutional Isomerism in Alkanes
2.3. Nomenclature of Alkanes and the IUPAC System
2.4. Cycloalkanes
2.5. Conformations of Alkanes and Cycloalkanes
2.6. Cis, Trans Isomerism in Cycloalkanes
2.7. Physical Properties of Alkanes and Cycloalkanes

Problems and Examples: 2.1-2.10, 2.12-2.14, 2.16-2.28, 2.33-2.35, 2.40, 2.42-2.43, 2.48

Chapter 3. STEREOCHEMISTRY AND CHIRALITY
3.1. Stereoisomerism
3.2. Chirality
How To: Draw Chiral Molecules
3.3. Naming Chiral Centers—The R,S Systems
How To: Assign R or S Configuration to a Chiral Center
3.4. Acyclic Molecules with Two or More Chiral Centers
3.5. Cyclic Molecules with Two or More Chiral Centers
3.6. Properties of Stereoismers
3.7. Optical Activity—How Chirality Is Detected in the Laboratory

Problems and Examples: 1-8, 14, 16-18, 20, 22, 25-27, 30, 31

Chapter 4. ACIDS AND BASES
4.2. Brønsted-Lowry Acids and Bases
4.3. Acid Dissociation Constants, pKa, and Strengths of Acids and Bases
4.4. The Position of Equilibrium in Acid-Base Reactions
4.6. Molecular Structure and Acidity
4.7. Lewis Acids and Bases

Problems and Examples: 4.1-4.4, 4.8, 4.9, 4.11, 4.6 (skip math), 4.26 (b, c)

Chapter 5. ALKENES
5.1. Structure of Alkenes
How To: Calculate the Index of Hydrogen Deficiency
5.2. Nomenclature of Alkenes
5.3. Physical Properties of Alkenes

Problems and Examples 5.1-5.2, 5.32, 5.33c, 5.34d, 5.3-5.7

Chapter 6. REACTIONS OF ALKENES
6.1. Reactions of Alkenes—An Overview
6.2. Organic Reactions Involving Reactive Intermediates
6.3. Electrophilic Additions
6.4. Hydroboration-Oxidation
6.5. Oxidation
6.6. Reduction

Problems: 1-13, 15-22, 24, 26, 30-34, 36, 37-41, 42, 44, 48

Chapter 7. ALKYNES
7.1. Structure of Alkynes
7.2. Nomenclature of Alkynes
7.4. Acidity of 1-Alkynes
7.5. Preparation of Alkynes
7.6. Electrophilic Addition to Alkynes
7.7. Hydration of Alkynes to Aldehydes and Ketones
7.8. Reduction of Alkynes
7.9. Organic Synthesis

Problems: 1-6, 8, 10-12, 16, 17, 20, 21, 23-25, 29-31

Chapter 8. HALOALKANES, HALOGENATION, AND RADICAL REACTIONS
8.1. Structure
8.2. Nomenclature
8.3. Physical Properties of Haloalkanes
8.4. Preparation of Haloalkanes by Halogenation of Alkanes
8.5. Mechanism of Halogenation of Alkanes
8.6. Allylic Halogenation
8.8. Radical Addition of HBr to Alkenes

Problems:  1, 2, 5-7, 8-10, 13, 14, 24-26, 28-30 

Chapter 9. NUCLEOPHILIC SUBSTITUTION AND β-ELIMINATION
9.1. Nucleophilic Substitution in Haloalkanes
9.2. Mechanisms of Nucleophilic Substitution
9.3. Experimental Evidence for SN1 and SN2 Mechanisms
9.4. Analysis of Several Nucleophilic Substitution Reactions
9.5. β-Elimination
9.6. Mechanisms of β-Elimination
9.7. Experimental Evidence for E1 and E2

Problems and Examples: 9.1-9.7

Chapter 10. ALCOHOLS
10.1. Structure and Nomenclature of Alcohols
10.2. Physical Properties of Alcohols
10.3. Acidity and Basicity of Alcohols
10.4. Reaction of Alcohols with Active Metals
10.5. Conversion of Alcohols to Haloalkanes and Sulfonates
10.6. Acid-Catalyzed Dehydration of Alcohols
10.8 (A and B). Oxidation of Alcohols

Problems and Examples: 10.1-10.9, 10.11