Organic Chemistry I/II - 2009-2010

Ch 24: Amines and heterocycles

Nomenclature; properties and basicity of amines; synthesis; reductive amination; Hoffman elimination; Sandmeyer reaction; heterocycles; spectroscopy

Ch 23: Carbonyl condensation reactions

Aldol reaction; dehydration; mixed aldol; intramolecular aldol; Claisen reaction (mixed, intramolecular); Michael reaction; Stork enamine reaction; Robinson annulation

Ch 22: Carbonyl alpha-substitution reactions

Keto-enol tautomerism; reactivity of enols; alpha-halogenation; enolate ion formation and reactivity; alkylation of enolate ions

Ch 21: Carboxylic acid derivatives

Naming; nucleophilic acyl substitution reactions; reactions of carboxylic acids; chemistry of acid halides, anhydrides, esters, amides; biological thioesters and acyl phosphates; step-growth polymers; spectroscopy

Ch 20a: Carboxylic acids

Carboxylic acid nomenclature; structure and properties; acidity; the Henderson-Hasselbalch equation; substituent effects on acidity; preparation; spectroscopy

Ch 19: Aldehydes and ketones: nucleophilic addition reactions

Aldehyde and ketone nomenclature; preparation of aldehydes and ketones; oxidation;hydration; cyanohydrin formation; Grignard and hydride reactions; imine and enamine formation; acetal formation; Wittig reaction; conjugate addition; spectroscopy

Ch 18: Ethers and epoxides; thiols and sulfides

Ether nomenclature, synthesis, cleavage; epoxide synthesis and ring-opening; thiols and sulfides; spectroscopy of ethers

Ch 17: Alcohols and phenols

Nomenclature; acid-base properties; synthesis of alcohols from alkenes; reduction of carbonyl compounds; Grignard reaction; conversion of alcohols into alkyl halides and tosylates; dehydration and oxidation of alcohols; protection; spectroscopy

Ch 16: Chemistry of benzene: electrophilic aromatic substitution

Bromination; other aromatic substitutions; alkylation of aromatic rings: the Friedel-Crafts reaction; substituent effects in aromatic rings; trisubstitued benzenes: additivity of effects; oxidation and reduction of aromatic compounds; synthesis

Ch 15: Benzene and aromaticity

Aromatic compound nomenclature; benzene MOs; 4n+2 rule; aromatic ions; aromatic heterocycles; polycyclic aromatic compounds; spectroscopy of aromatic compounds

Ch 14: Conjugated compounds and UV spectroscopy

Conjugation, MOs, allylic carbocations, Diels-Alder reaction, UV spectroscopy

Ch 12: Mass spectrometry and infrared spectroscopy

MS theory; interpretation of mass spectra; IR theory, interpretation of IR spectra

Jan 12: Intro to 2062

Ch 13: Nuclear magnetic resonance spectroscopy

NMR absorptions; chemical shift; 13C NMR; 1H NMR; integration; spin-spin splitting

Ch 11: Substitution and elimination

SN2 reaction; SN1 reaction; elimination reactions and Zaitsev's rule; E2 reaction and cyclohexane conformation; E1 reaction; summary of reactivity; synthesis practice

Nov 24: Exam 3 review; substitution and elimination

CA 13, CA 14

Ch 10: Organohalides

Nomenclature and structure of organohalides; radical halogenation; preparation of organohalides; Grignard and Gilman reagents

Ch 9: Stereochemistry

Chirality; enantiomers; assigning configuration; diastereomers; meso compounds; racemic mixtures; stereochemistry of reactions

Nov 17: Radical halogenation

CA 15, CA 13A

Ch 8: Alkynes: an intro to organic synthesis

Nomenclature; preparation of alkynes; addition of HX and X2; hydration and tautomerism; reduction; formation and alkylation of acetylide ions