Download CHEM 2412

Chemistry Courses Topics Lists
Last updated: 3/24/10
Course Name and Number: ___CHEM 2412: Organic Chemistry II_____________
Instructors: _ Clower , Hornbuckle, Kirberger _____________
List of topics that should be covered in this course:
(Mechanism should be covered for each reaction listed below unless noted.)
Reactions of Alkenes
Addition Reactions with symmetrical addition reagents (H2, Br2, Cl2); Addition Reactions with
asymmetrical addition reagents (H2O, HBr, HCl, Hg(OAc)2 and H2O then NaBH4); Markovnikov’s Rule;
Carbocation Rearrangement; Anti-Markovnikov Addition (HBr and ROOR, hydroboration-oxidation);
Halohydrin synthesis; Stereochemistry of addition reactions; Epoxidation; Glycol formation; Ozonolysis
and oxidative cleavage by permanganate
Alkynes
Nomenclature and drawing of alkynes; Physical properties of alkynes; Hybridization and bond lengths, scharacter; Acidity of terminal alkynes; Acetylide formation and reactions with alkyl halides and carbonyl
compounds; Elimination reactions used to form alkynes (terminal/internal isomerization); Addition
reactions (H2 with and without Lindlar’s Catalyst, Br2, Cl2, H2O, HBr, HCl, oxymercurationdemercuration, HBr and ROOR, hydroboration-oxidation); Enol-keto tautomerism
Structures and Synthesis of Alcohols
Nomenclature and drawing of alcohols (including hydroxyalkyl groups, diols, triols); Common names of
alcohol of 4 carbons or less; Primary, secondary, tertiary alcohols; Physical properties of alcohols; Phenol
(very briefly); Absolute alcohol; Denatured alcohol; Acidity of alcohols and phenols; Formation of
alkoxide ions; Review methods of alcohol synthesis covered in earlier chapters; Grignard reagents
(reactions with ketones, aldehydes, esters, acid halides, epoxides); Functional groups that interfere with
Grignard Reactions; Reduction reactions using sodium borohydride, lithium aluminum hydride, and H2
with Raney Ni; Organolithium reagents
Reactions of Alcohols
Oxidation of alcohols: Chromic acid reagents, PCC, Swern Oxidation (no mechanism); Formation of
tosylate esters; Methods for reducing alcohols; SN1 and SN2 reactions; Lucas Reagent; PX3 (with
stereochemistry); SOCl2 (with stereochemistry); Dehydration reactions reviewed; Pinacol Rearrangement;
Esterification of alcohols (Fischer esterification, acid chlorides); Williamson ether synthesis
Aromatic Compounds
Benzene structure and stability; Historical structure deduction (Kekulé); Unusual reactions of benzene;
Resonance stabilization; Aromatic, Antiaromatic and Nonaromatic compounds; Huckel’s Rule; Aromatic
ions; Pyridine, pyrrole, furan; Nomenclature and drawing of benzene derivatives (including phenyl and
benzyl groups); Physical properties of aromatic compounds
Reactions of Aromatic Compounds
Electrophilic Aromatic Substitution; Br2/FeBr3; Cl2/AlCl3; I2 + HNO3; Nitration; Sulfonation;
Desulfonation; ortho para-directors; meta-directors; activating and deactivating groups; inductive effect
and resonance effect; Friedel-Crafts Alkylation and limitations; Friedel-Crafts Acylation; Clemmensen
Reduction; Gattermann-Koch Formylation; Permanganate oxidation of side chains; Halogenation in the
benzyllic position
Ketones and Aldehydes
Carbonyl group; Ketone nomenclature and structure drawing; Aldehyde nomenclature and structure
drawing; Oxo and formyl groups; Oxa groups; Carbaldehyde groups; Physical properties of ketones and
aldehydes; Review ketone and aldehyde preparations covered in earlier chapters; Synthesis of aldehydes
and ketones using 1,3-dithianes; Synthesis of ketones from carboxylic acids; Synthesis of aldehydes and
ketones from carboxylic acids; Nucleophilic addition to aldehydes and ketones; Formation of
cyanohydrins; Formation of imines (Schiff Base); Formation of hemiacetals and acetals; Acetals as
protecting groups; Oxidation of aldehydes vs. ketones; Hydration of carbonyl groups reviewed; WolffKishner reduction; Clemmenson reduction reviewed
Amines
Chemistry Courses Topics Lists
Last updated: 3/24/10
Amine nomenclature and structure drawing (including ammonium salts, amino groups); Primary,
secondary, tertiary amines; Physical properties of amines: odor, boiling points, solubility, pH,
intermolecular forces; Relative basicity of nitrogen containing organic compounds; Acid-base reactions;
Alkylation of amines; Acylation of amines
Carboxylic Acids
Carboxylic acid and carboxylate salt nomenclature and structure drawing; Physical properties of
carboxylic acids: odor, boiling points, solubility, pH, intermolecular forces; Relative acidity of substituted
carboxylic acids; Acid-base reactions; Properties of carboxylate salts; Preparations of carboxylic acids:
Oxidation of primary alcohols, Oxidative cleavage of alkenes and alkynes, Oxidation of alkyl benzenes,
Carboxylation of Grignard reagents; Chemical reactions of carboxylic acids: Fischer esterification, Acid
chloride synthesis, Acid anhydride synthesis, Amide synthesis, Reduction of carboxylic acids, Alkylation
of carboxylic acids to form ketones – reviewed
Carboxylic Acid Derivatives
Acid chloride, Acid anhydride, ester, amide nomenclature and structure drawing
Physical properties of acid chlorides, acid anhydrides, esters, and amides: odor, boiling points, solubility,
pH, intermolecular forces; Interconversion of acid derivatives by nucleophilic acyl substitution;
Transesterification; Hydrolysis of acid derivatives
List of optional topics that can be taught in this course:
Carbene addition to alkenes, Polymerization of alkenes
Thiols
Phenol synthesis using H2O2 and FSO3H, Birch Reduction
Nucleophilic Aromatic Substitution
Benzyne
Wittig Reaction
Nitrile chemistry
The Hofmann Elimination
The Cope Elimination
Reactions of amines with nitrous acid
Reactions of Arenediazonium salts
The Sandmeyer reaction
Reductive amination
Acylation-reduction to synthesize amines