CHEM 2724: Organic Chemistry II

1) Infrared Spectroscopy: absorption spectroscopy, electromagnetic spectrum, c=λν,
E=hv, photons, infrared region, wavenumbers, molecular
vibrations, infrared spectrum, bond stretching frequencies, finger
print region, IR active and inactive vibrations, infrared
spectrometer, FT-IR, reading and interpreting IR spectra (C-C
bond stretching, conjugation, C-H bond stretching,
characteristics of alcohols, amines, carbonyl compounds, C-N
bonds, etc)

2) Mass Spectrometry: the mass spectrometer, electron impact ionization, fragmentation,
molecular ion, separation of ions by mass, the mass spectrum,
base peak, GC-MS, HRMS, fragmentation patterns in MS,
reading and interpreting mass spectra
Interpreting IR and MS together
3) Nuclear Magnetic Resonance Spectroscopy: NMR
theory, nuclear spin, magnetic field, NMR absorption, shielding,
NMR spectrometer, chemical shift, TMS, proton NMR chemical
shifts, number of signals, chemically equivalent protons, area of
peaks, measuring integral traces, splitting, N+1 rule, multiplet
leaning, coupling constants, reading and interpreting Proton
NMR spectra, C-13 NMR spectroscopy, carbon chemical shifts, comparison
between proton and C-13, splitting, off-resonance decoupling,
interpreting C-13 NMR spectra, using IR, MS, HNMR and C-13
NMR to deduce structure of an unknown compound

4) Ethers, Epoxides and Thioethers:
Ethers: structure, physical properties, as solvents, as
complexes, IUPAC nomenclature, common names, cyclic
ethers, Williamson ether synthesis, synthesis of phenyl ethers,
alkoxymercuration-demercuration, bimolecular condensation of
alcohols, cleavage of ethers by HBr and HI, autooxidation of
ethers
Thioethers: properties, naming, synthesis via Willamson,
generation of thiolate ions, oxidations, as nucleophiles
Silyl ethers: as alcohol protecting groups
Epoxides: synthesis, peroxyacid epoxidation, cyclization of
halohydrins, acid and base catalyzed ring opening of epoxides,
reactions with Grignards and organolithiums

5) Conjugated Systems, Orbital Symmetry and
Ultraviolet Spectroscopy: conjugation, stability of dienes,
Molecular orbitals of conjugated systems, allylic cations, 1,2-and
1,4-additions, kinetic and thermodynamic control in additions,
allylic radicals, molecular orbitals of allylic systems, allylic
anions, SN2 reactions of allylic halides and tosylates, Diels-Alder reaction mechanism,
Ultraviolet absorption spectroscopy, absorptions and electronic
transitions, Beer’s law, interpreting UV-Vis spectra

6) Aromatic Compounds: structure, properties, stability,
MOs, energy diagrams of benzene, Aromatic, Antiaromatic and
Nonaromatic compound/ion criteria, Huckel’s Rule, IUPAC
Nomenclature of benzene derivatives, physical properties

7) Reactions of Aromatic Compounds: electrophilic
aromatic substitution reaction/mechanism, halogenation,
nitration, sulfonation of benzene and substituted benzene,
activating and deactivating groups, ortho-, para-, meta- directing
substituents, effect of multiple substituents on EAS,
Friedel-Crafts alkylation and acylation reaction mechanisms,
Clemmensen reduction, nucleophilic
aromatic substitution mechanisms (addition-elimination and
elimination-addition), substitutions using organometallics, Heck
reaction, Suzuki reaction, addition reactions of benzene derivatives, catalytic
hydrogenation of aromatic rings, Birch reduction, oxidation of
phenols, EAS of phenols

8) Ketones and Aldehydes: carbonyl structure, IUPAC
nomenclature of ketones and aldehydes, common names,
physical properties of ketones and aldehydes, industrial
importance, synthesis of ketones and aldehydes (review:
oxidation of alcohols, ozonolysis of alkenes, Friedel-Crafts
acylation, hydration of alkynes), synthesis of ketones from
carboxylic acids/organolithiums, ketones and aldehydes from
nitriles/organometallics, reduction of nitriles using Al hydrides,
aldehydes and ketones from acid chlorides and esters, reactions of ketones and
aldehydes: nucleophilic addition to carbonyl groups mechanism,
hydration, formation of cyanohydrins, imines, condensations
with amines, formation of acetals, acetals as protecting groups,
Wittig reaction, oxidation of aldehydes, reductions of ketones
and aldehydes

9) Amines: Primary, secondary, tertiary amines, quaternary
ammonium salts, IUPAC nomenclature and common names,
structure, physical properties, basicity and factors affecting,
basicity, electrophilic aromatic substitution of
arylamines/pyridine, nucleophilic aromatic substitution of
pyridine, alkylation and acylation of amines, formation of
sulfonamides, Hofmann Elimination, oxidation of amines, the
Cope elimination, diazotination, synthesis, reductive amination,
acylation-reduction, alkylation, reductions

10) Carboxylic Acids: carboxyl group, carboxylate ion,
nomenclature, common and IUPAC, dicarboxylic acids, structure
and physical properties, acidity, factors that affecting, salts of
carboxylic acids, commercial sources, synthesis, oxidations from
alcohols and aldehydes, from alkenes, oxidation of
alkylbenzenes, carboxylation of Grignard reagents, hydrolysis of nitriles, reactions of carboxylic acids and
derivatives, nucleophilic acyl substitution, condensations,
Fischer Esterification, using diazomethane, acids with amines,
reduction of carboxylic acids, alkylation of carboxylic acids,
synthesis and use of acid chlorides

11) Carboxylic Acid Derivatives: Structure and IUPAC
nomenclature of esters, amides, nitriles, acid halides, acid
anhydrides, and multifunctional groups, physical properties,
addition-elimination of nucleophilic acyl substitution, reactivity,
interconversions, acid chloride to anhydride, ester, amide, acid
anhydride to ester, amide, ester to amide, transesterification,
hydrolysis of acid halides, anhydrides, esters (saponification),
amides, nitriles, reduction of acid derivatives to alcohols,
aldehydes, amines, reactions with organometallics

12) Condensations and Alpha Substitutions of Carbonyl
Compounds: alpha substitution, condensations, addition of
enolate to aldehydes and ketones, substitution of an enolate on
an ester, keto-enol tautomerism, alkylation of enolate ions,
formation and alkylation of enamines, alpha halogenation of
ketones, alpha bromination of carboxylic acids, acid and base
catalyzed aldol condensation, dehydration of an aldol, crossed
condensations, aldol cyclizations, Claisen ester condensation,
syntheses, using β-dicarbonyl compounds, Malonic ester
synthesis, acetoacetic ester synthesis