CHM 235 Course Outline and Homework in McMurry (6th ed.)
Fall 2006
Chapter 1: 1.19-1.26, 1.28-1.31, 1.34, 1.36-1.39, 1.46, 1.47
 Atomic orbitals (s,p), electronic configuration (through calcium)
 Covalent vs ionic bonds, Lewis structures, valence electrons
 Valence bond theory, hybridization (sp3, sp2, sp, N and O)
 Molecular shape (tetrahedral, trigonal planar, linear), molecular orbital theory
Chapter 2: 2.25-2.31, 2.35-2.37, 2.39-2.41, 2.43-2.46, 2.49, 2.55, 2.56
 Polar covalent bonds, electronegativity, dipole moments
 Formal charge
 Resonance
 Acids and bases (B-L, and Lewis), pKA
 Drawing condensed and skeletal structures
Chapter 3: 3.23-3.28, 3.30, 3.32, 3.34, 3.36, 3.39, 3.44-3.49, 3.53, 3.54
 Functional groups (alkanes, alkenes, alkynes, halides, alcohols, ethers, amines,
nitriles, aldehydes, ketones, carboxylic acids, esters, amides)
 Constitutional isomers
 Nomenclature of straight-chain alkanes (up to dodecane), branched alkanes, alkyl
groups, and cycloalkanes (including cis/trans)
Chapter 4: 4.24-4.26, 4.29-4.32, 4.38, 4.41, 4.42, 4.46
 Sawhorse and Newman projections
 Conformations of ethane, propane, butane (staggered, eclipsed, gauche, anti)
 Ring strain, steric strain
 Conformations of cyclohexane (axial and equatorial hydrogens, ring flip, mono and
disubstituted cyclohexanes)
Chapter 5: 5.19, 5.21, 5.23, 5.24, 5.27, 5.28, 5.30, 5.32, 5.37, 5.39-5.42, 5.47
 Overview to addition, elimination, substitution, and rearrangement reactions
 Free radical halogenation reactions (initiation, propagation, termination)
 Polar reactions (electrophile, nucleophile)
 Curved arrow formalism (“arrow-pushing”) to show reaction mechanisms
 Thermodynamics (Go = Ho - TSo) (exergonic, endergonic, exothermic,
endothermic)
 Bond dissociation energies (Ho = energy used to break bonds–energy gained by
making bonds)
 Energy diagrams (reaction coordinates, transition states, reaction intermediates, RDS)
1
Chapter 6: 6.23-6.32, 6.39-6.44, 6.78, 6.48
 Degree of unsaturation in alkenes
 Naming alkenes
 Cis/trans isomerism and E, Z designation
 Alkene stability (most substituted alkene is the most stable) and hyperconjugation
 Electrophilic addition of HX across the double bond (Markovnikov’s rule)
 Carbocation stability (30 more stable than 20 more stable than 10) and rearrangements
 Hammond postulate
 Rearrangement reactions (H- and CH3- transfer)
Chapter 7: 7.23-7.30, 7.32-7.36, 7.40-7.44
 Preparation of alkenes: elimination reactions (reactions 1a, 1b)
 Addition of HX (rxn 2a), X2 (rxn 2b), X2 + H2O (2c)
 Addition of H2O: acid catalyzed hydration, oxymercuration (rxn 2d), hydroboration
(rxn 2e)
 Syn addition of H2 (hydrogenation) (rxn 2f)
 Syn addition of OH (hydroxylation) (rxn 2g)
 Addition of carbenes to alkenes (rxns 2h1 and 2h2)
 Oxidative cleavage reactions: ozonolysis (rxn 3a), aqueous acidic KMnO4 (rxn 3b),
and HIO4 (rxn 4)
 Polymerization
Chapter 8: 8.19-8.29, 8.31-8.37
 Electronic structure and IUPAC names for alkynes
 Preparation of alkynes: elimination reactions (rxn 1a)
 Addition of HX (rxn 2a) and X2 (rxn 2b)
 Addition of H2O: Hg(II)-catalyzed hydration (rxn 2c) and hydroboration/oxidation
(rxn 2d)
 Addition of H2 (reduction) (rxn 2e1 and 2e2)
 Oxidative cleavage (rxn 2h)
 Alkyne acidity and formation of acetylide anions (R—CC) (rxn 1b)
 Alkylation of acetylide anions, a substitution reaction (rxn 1b)
 Introduction to organic synthesis (the fun part!)
Chapter 9: 9.34-9.36, 9..38-9.46, 9.51-9.55, 9.65, 9.67, 9.79, 9.80
 Enantiomers, chirality, specific rotation
 Sequence rules for R and S
 Diastereomers and meso compounds
 Racemic mixtures and their resolution (chiral drugs!)
 Fischer projections
 Stereochemistry in reactions (addition of HBr, Br2)
2
Chapter 10: 10.17-10.25, 10.28, 10.31-10.33, 10.36-10.38, 10.40
 Naming alkyl halides
 Preparation of alkyl halides using free radical halogenation
 Preparation of alkyl halides by addition to alkenes (rxn 1b), allylic bromination of
alkenes (rxn 1a); substitution reactions with alcohols (rxns 1c1-1c3)
 Stability of the allylic radical
 Grignard reagent formation (rxn 2a), Gilman reagent formation (rxn 2b)
 Reactions of Grignards and Gilman reagents (rxns 2c and 2d)
 Oxidation/reduction reactions in organic chemistry
Chapter 11: 11.25-11.31, 11.34-11.38, 11.41, 11.45-11.47, 11.50, 11.54, 11.55, 11.5911.60, 11.68
 The SN2 substitution reaction (stereochemistry, kinetics, the substrate, the attacking
nucleophile, the leaving group, the solvent) (rxn 1b)
 The SN1 substitution reaction (stereochemistry, kinetics, the substrate, the attacking
nucleophile, the leaving group, the solvent) (rxn 1a)
 The E2 elimination reaction and Zaitsev’s rule (rxn 2b)
 The E1 elimination reaction (rxn 2a)
Chapter 12: 12.17-12.19, 12.28-12.30, 12.34-12.40
 Introduction to mass spectrometry
 Introduction to IR spectroscopy
Chapter 13: 13.31-13.32, 13.35-13.44, 13.46, 13.49-13.52 (and maybe some others)
 Introduction to NMR and chemical shift
 13C NMR and DEPT 13C NMR
 1H NMR (proton equivalence, chemical shifts, integration, spin-spin splitting,
complex spin-spin splitting)
3