Organic Chemistry Objectives

Objectives for CHEM 211

Lecture

Instructors in CHEM 211 agree to cover the following lecture topics. They may choose

to cover more, but they must not include material that the Department agrees will be

reserved for CHEM 212. Instructors are free to cover this material in the order they find

most convenient.

Fundamentals

  • Structural theory, Lewis structures, isomers, basic resonance theory
  • Atomic, molecular, and hybrid orbitals, covalent bonding, shapes of molecules
  • Polarity of molecules and bonds
  • Physical properties and intermolecular forces
  • Functional groups and families of organic compounds
  • Acid and base properties, equilibria, and relative acid/base strengths
  • Potential energy diagrams of reactions, activation energies of reactions

Introduction to Mechanisms and Synthesis

  • Introduction to mechanisms
  • Curved arrow notation
  • Basic retrosynthetic analysis
  • Synthesis of alkanes, alkenes, and alkynes

Organic Nomenclature

  • IUPAC Nomenclature of alkanes, cycloalkanes, bicycloalkanes, alkenes,
  • cycloalkenes, alkynes, alkyl halides, and alcohols
  • R/S Nomenclature system for chiral molecules
  • E/Z Nomenclature system for alkenes

Stereochemistry

  • Chirality
  • Optical activity, specific rotation, optical purity, enantiomeric excess
  • Enantiomers, diastereomers
  • Cyclic compounds
  • Ring strain and conformations of cycloalkanes
  • Stereochemistry in reactions
  • Resolution of a racemic mixture

Hydrocarbons (Alkanes, cycloalkanes, alkenes, and alkynes)

  • Structure and physical properties
  • Conformational analysis of ethane and higher alkanes
  • Relative stabilities of alkenes and alkynes

Reactions

  • Nucleophilic substitution reactions (SN2 and SN1)
  • Elimination reactions (E2 and E1)
  • Hydrogenation of alkenes and alkynes
  • Reduction of alkyl halides
  • Alkylation of terminal alkynes
  • Dehydrohalogenation of alkyl halides, Zaitsev and Hofmann rules
  • Dehydration of alcohols
  • Rearrangements of carbocation intermediates
  • Debromination of vicinal dibromides
  • Addition of hydrogen halides, sulfuric acid, water, and halogens to alkenes andalkynes
  • Formation of halohydrins
  • Oxidations of alkenes and alkynes, syn hydroxylation, oxidative cleavage,ozonolysis

Laboratory

Instructors in CHEM 211 Laboratory are expected to include background theory and

experiments covering the topics listed below. The schedule will allow for one or two

additional synthesis or reaction labs. Currently, an alcohol dehydration lab and a

spectroscopy review session complete the schedule.

  • Techniques – melting points, recrystallization, extraction, distillation, gas and thinlayer chromatography
  • Spectroscopy – infrared, proton nuclear magnetic resonance
  • Stereochemistry with molecular models
  • SN1 and SN2 reactions

Objectives for CHEM 212

Lecture

Instructors in CHEM 212 agree to cover the following lecture topics. They may choose

to cover more, but these topics must be included. They cannot assume their students

have exposure to topics not on the departmentally approved list of CHEM 211

objectives. Instructors are free to cover this material in the order they find most

convenient.

Fundamentals

  • Homolytic bond dissociation energies
  • IUPAC Nomenclature of alcohols, ethers, aromatic compounds, carbonyl compounds, and amines
  • Structures and properties of alcohols, ethers, alkadienes and polyunsaturated hydrocarbons, aromatic compounds, carbonyl compounds, and amines
  • Physical properties of alcohols, ethers, aromatic compounds, carbonyl compounds, and amines
  • Aromaticity of benzene and other aromatic compounds
  • Stability of allylic radicals and cations, conjugated dienes
  • Resonance theory
  • Acidity of alpha-hydrogens of carbonyl compounds
  • Keto-enol tautomerism

Mechanisms and Synthesis

  • Mechanisms of most reactions listed below
  • Retrosynthetic analysis
  • Synthesis of major classes of organic compounds, alkanes, alkyl halides, alcohols, ethers, carbonyl compounds, and amines

Reactions

  • Free radical reactions, halogenation of alkanes, radical addition to alkenes
  • Synthesis of alcohols from alkenes, acid catalyzed hydration, oxymercurationdemercuration, hydroboration-oxidation, Grignard reaction
  • Conversion of alcohols into mesylates and tosylates, mesylates and tosylates in
  • nucleophilic substitution reactions
  • Conversion of alcohols into alkyl halides, reacting alcohols with HX or PBr3 or SOCl2
  • Synthesis of ethers, intermolecular dehydration of alcohols, Williamson synthesis, ethers as protecting groups
  • Reactions of ethers, cleavage of ethers by strong acids
  • Alkene epoxidation, acid and base ring-opening of epoxides
  • Reduction of carbonyl compounds
  • Oxidation of alcohols
  • Preparation and reactions of organometallic compounds, Grignard reaction, lithium dialkylcuprates, Corey-House reaction
  • Allylic substitution, 1,4-addition reactions of conjugated dienes, Diels-Alder reaction
  • Electrophilic aromatic substitution reactions, halogenation, nitration, sulfonation,
  • Friedel-Crafts alkylation, Friedel-Crafts acylation, effects of substitutents on reactivity and orientation
  • Reactions of alkyl side chains on aromatic rings, benzylic halogenation, addition to alkenyl benzenes, oxidation of alkyl side chains
  • Nucleophilic addition reactions of aldehydes and ketones, Grignard reaction, addition of hydride ion, addition of hydrogen cyanide, Wittig reaction, addition of derivatives of ammonia
  • Acid and base-catalyzed enolization of ketones
  • Halogenation of aldehydes and ketones, haloform reaction
  • Aldol addition and condensation reactions, Claisen-Schmidt reaction, lithium enolates
  • Reactions of carboxylic acids, relative acidity, reduction reactions, conversion to acyl chlorides, acid anhydrides, esters, lactones, amides, and lactams
  • Reactions of acyl chlorides – conversion to acids, anhydrides, esters, amides, ketones, and aldehydes
  • Reactions of acid anhydrides – conversion to acids, anhydrides, esters, amides, and aryl ketones
  • Reactions of esters – acid and base hydrolysis, conversion to other esters and amides, reaction with Grignard reagents, reduction reactions
  • Reactions of amides – hydrolysis, conversion to nitriles
  • Reactions of nitriles – hydrolysis, reductions, conversion to ketones
  • Synthesis of amines – Gabriel synthesis, reduction of alkyl azides, nitriles, oximes, and amides, amination of alkyl halides, reduction of nitroarenes, reductive amination
  • Reactions of amines – relative basicity, diazotization of primary arylamines and replacement of the diazonium group, conversion to amides or sulfonamides

Laboratory

Instructors in CHEM 212 Laboratory are expected to include background theory and

experiments covering the topics listed below. The schedule will allow for several

additional synthesis or reaction labs. Currently, labs dealing with the reactions of

hydrocarbons, alcohols, and aldehydes and ketones and synthesis labs involving the

Diels-Alder reaction and oxidation and reduction reactions complete the schedule.

  • Free-radical halogenation
  • Grignard synthesis
  • Electrophilic aromatic substitution
  • Organic polymers
  • Unknowns with 13C NMR spectroscopy
  • Introduction to carbohydrates