Download Organic Chemistry –Syllabus- one Semester Sackler faculty of

Organic Chemistry –Syllabus- one Semester
Sackler faculty of medicine
Tel-Aviv University-Israel
CONTENTS:
Electronic Structure and Bonding, Acids and Bases
The Structure of an Atom, The Distribution of Electrons in an Atom, Ionic, Covalent,
and Polar Bonds, Lewis Structures, Skeletal Structure (Line-Bond Structure), Formal
Charge, Bond strength, Bond length, Hybridization(sp3, sp2, sp), geometry of
molecules, Dipole Moment, Functional Groups , Resonance, Acids and Bases: The
Brønsted-Lowry Definition, conjugation acid-base pair, Ka ,pKa ,Kb, how to
determine the position of acid-base reaction, The Effect of Structure on pKa, The
Henderson–Hasselbalch Equation, A buffer Solution, Lewis Acids and Bases.
Organic Compounds + Alkanes
double bond equivalent, alkyl group, Nomenclature (IUPAC rules), intermolecular
forces( van der Waals force, Dipole–dipole interaction, Hydrogen bonds), Solubility,
Conformations of alkanes(staggered-eclipsd) , Cycloalkanes, geometric isomers, The
chair conformation of cyclohexane, Combustion of alkanes, Oxidation and Reduction
in Organic Chemistry, Halogenation of alkanes.
Stereochemistry
Classification of Isomers, Chirality, Enantiomers, Achiral molecules, chirality center,
Meso compounds, Naming Enantiomers ( R,S configurations), Fischer Projection,
Optical Activity, Racemic Mixture, Diastereomers, Resolution of a Racemic Mixture,
Discrimination of Enantiomers by Biological Molecules.
Substitution and Elimination reactions
substitution and elimination reactions- definitions, Thermodynamics and Kinetics
(activation energy, transition state, intermediate product, reaction order, Catalysis,
free energy, exergonic and endergonic reaction reaction), Mechanism of an SN2
Reaction, Nucleophilicity, Mechanism of an SN1 Reaction, rearrangement,
Mechanism of an E1 and E2Reactions, SN2- SN1 conditions, Competition Between
Substitution and Elimination, Williamson ether synthesis, SAM Reagent.
Alcohols and Ethers
Converting Alcohols into Alkyl Halides, Dehydration of Alcohols, Alcohol oxidation,
Acid-base catalyzed ring-opening of epoxides, Grignard Reagents, Biological
Oxidants and Reductants.
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Alkenes
Nomenclature , Structure and Properties, Addition of Hydrogen Halides,
Markovnikov’s Rule, Addition of Water, Addition of Halogens, addition of A
Peroxyacids to an Alkene, Hydroboration, anti-Markovnikov addition of HBr,
Addition of Hydrogen, Relative Stabilities of Alkenes, Ozonolysis, reaction of alkene
with KMnO4.
Alkynes and Dienes
Nomenclature , Structure and Properties, Addition of Halogens and Hydrogen to
alkynes, Addition of Water (Markovnikov and anti-Markovnikov), complete
hydrogenation of alkyne, Lindlar Reduction, Reduction With Na or Li, alkylation.
Dienes: 1,2 and 1,4 additions of Conjugated Dienes, Thermodynamic Versus Kinetic
Control, The Diels–Alder Reaction.
Carboxylic acid derivatives
Nomenclature , Structure and Properties, Addition-Elimination Mechanism, Reactions
of Acyl Halides, Reactions of Acid Anhydrides, Reactions of Esters, Ester
Hydrolysis, Fischer esterification, reaction of amides and carboxylic acids, Hydrolysis
of Nitriles, Activation of Carboxylic Acids, Dicarboxylic Acids, Reaction of esters,
acyl halides and Nitriles with Grignard Reagents, reduction of esters, carboxylic
acids, acyl halides , amides and nitriles.
Aldehydes and Ketones + Reactions at the α-Carbon
Nomenclature , Structure and Properties, Reactions of Aldehydes and Ketones with
Grignard Reagents, cyanide ion, acetylide ion, hydride and Nitrogen Nucleophiles.
Reductive amination, reduction of ketones to alkanes, ketones oxidation, Reactions of
Aldehydes and Ketones with water and Alcohols.
Reactions at the α-Carbon: Acidity of α –Hydrogens, Keto–Enol Tautomerism,
Halogenation of the α -Carbon of Aldehydes and Ketones, Enolization, Alkylation of
the α -Carbon of Carbonyl Compounds, The Michael Reaction, aldol condensation,
Claisen Condensation, Dieckmann condensation, Decarboxylation, The Malonic Ester
Synthesis, The Acetoacetic Ester Synthesis, A Biological Aldol and Claisen
condensations, Fatty acid biosynthesis.
Aromatic compounds
Aromaticity, Nomenclature , Structure and Properties, Electrophilic
Aromatic Substitution Reactions, Halogenation, Nitration, Sulfonation, Friedel–Crafts
Acylation, Friedel–Crafts Alkylation, activating and deactivating substituents, ortho–
para directors, meta directors, Reducing a Nitro Substituent, oxidation of Alkyl
Substituents.
If time allows we will learn in general some of the following topics:
Proteins, carbohydrates, nucleic acids, lipids, metabolic pathways, Identification of
organic compounds (UV, IR, MS, NMR), Drugs.
Bibliography:
1.Organic chemistry,P. Bruice, 6th edition.
2.Organic chemistry, J. McMurry, 8th edition.
3. Fundamentals of Organic Chemistry,J. McMurry, 7th edition.
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