Chemistry 210 - Review Sheet for Exam #3

You should be familiar with key terms listed below. You should solve the assigned problems. Some of these problems, or problems very similar, will be on the exam.  If you can solve them, you should do well on the exam.

Chapter 7 Molecular Chirality Enantiomers The Chirality Center Symmetry in Achiral Structures Optical Activity Absolute and Relative Configuration The Cahn-Ingold-Prelog R-S Notation System Fischer Projections Properties of Enantiomers Chiral Drugs Reactions That Create a Chirality Center Chiral Molecules With Two Chirality Centers Achiral Molecules With Two Chirality Centers Chirality of Disubstituted Cyclohexanes Molecules With Multiple Chirality Centers Reactions That Produce Diastereomers Resolution of Enantiomers Stereoregular Polymers Chirality Centers Other Than Carbon Chiral carbons asymmetric carbons stereocenter carbons Enantiomers Diastereomers meso plane of symmetry optical activity plane-polarized light polarimeter observed rotation (α) specific rotation ([α]) Chapter 8: Nucleophilic Substitution Functional Group Transformation by Nucleophilic Substitution Relative Reactivity of Halide Leaving Groups The SN2 Mechanism of Nucleophilic Substitution

Chapter 8 (continued) Stereochemistry of SN2 Reactions How SN2 Reactions Occur Steric Effects in SN2 Reactions Nucleophiles and Nucleophilicity An Enzyme-catalyzed Nucleophilic Substitution of and Alkyl Halide The SN1 Mechanism of Nucleophilic Substitution Carbocation Stability SN1 Reaction Rates Stereochemistry of SN1 Reactions Carbocation Rearrangements in SN1 Reactions Effect of Solvent on the Rate of Nucleophilic Substitution Substitution and Elimination as Competing Reactions Sulfonate Esters as Substrates in Nucleophilic Substitution Chapter 9 -- Alkynes Sources of Alkynes Nomenclature Physical Properties of Alkynes Structure and Bonding in Alkynes: sp Hybridization Alkynes Preparation of Alkynes by Alkylation of Acetylene Preparation of Alkynes by Elimination Reactions alkyne nomenclature alkyne structure terminal alkyne internal alkyne alkynes as acids sodium amide (NaNH2) nucleophilic acetylide anions electrophilic addition hydrogen halide reactions hydration - enols keto-enol tautomerism Lindlar catalyst hydrogenation Na reduction of alkynes free radicals

Chapter 9 (continued) cis (Z) - trans (E) hydrogenation Reactions of Alkynes Hydrogenation of Alkynes Metal-Ammonia Reduction of Alkynes Addition of Hydrogen Halides to Alkynes Hydration of Alkynes Addition of Halogens to Alkynes Ozonolysis of Alkynes Chapter 10 Conjugation in alkadienes and Allylic Systems The Allyl Group Allylic Carbocations Allylic Free Radicals Allylic Halogenation Classes of Dienes Relative Stabilities of Dienes Bonding in Conjugated Dienes Bonding in Allenes Preparation of Dienes Addition of Hydrogen Halides to Conjugated Dienes Halogen Addition to Dienes Diene Polymers The Diels-Alder Reaction Ethylene and 1,3-Butadiene Diels-Alder Reaction Chapter 13: NMR chemical-shift equivalent integration spin-spin coupling nuclear spin magnetic moment relaxation shielding deshielding equivalent hydrogens equivalent carbons doublets & triplets