Rutgers Chemistry Courses – Organic Chemistry 2 in PDF by Alex J. Roche Rutgers University, Department of Chemistry. All official syllabi / course can be found in the online web post. Clickable Lecture Notes are based on the excellent books “Organic Chemistry” by L.G. Wade, Jr., 4th…9th eds.
ORGANIC CHEMISTRY 2
Chemistry is the molecular science. Chemists believe that the best understanding of the properties of matter comes from study at the molecular level.
For example, boiling points, acidity, chemical reactivity, taste, smell, drug efficacy, colour, toxicity, etc., can all be understood/predicted/explained by a consideration of the relevant atoms and bonds connecting them.
Organic chemistry provides the basic principles that govern the structure (and therefore the behavior and reactivity) of molecules.
This course builds upon the foundational principles mastered in Organic Chemistry I, and upon successful completion, students will understand the direct connection between the properties and behavior of a substance, and its molecular structure.
- Learning goals:
Students will be familiar with the following subject matter, and be able to apply these
concepts and principles to any molecule or chemical process.
Chapter 14 deals with Ethers and Cyclic ethers; their uses, syntheses, IUPAC naming and reactions; ring opening of epoxides, acid and base catalyzed differences in regiochemistry of nucleophilic ring opening.
Chapter 15 deals with the concept of Conjugation; different types of diene; the M.O. description of π bonds and conjugated π bonds; s-cis and s-trans conformations; 1,2 and 1,4 additions; kinetic and thermodynamic control; allylic systems; Diels Alder reactions; Woodward-Hoffmann rules, HOMO-LUMO interactions, Allowed and Forbidden Pericyclic processes; UV spectroscopy.
Chapter 16 deals with the special reactivity of Benzene; its structure, MO description; closed bonding shell; cyclobutadiene and its structure, reactivity and MO description; Polygon Rule; the distinction of Aromatic, Anti-aromatic and Non-aromatic; Huckel 4N+2 rule; aromatic ions and heterocycles; structure and reactivity differences for Pyridine and Pyrrole.
Chapter 17 deals with reactions of Aromatic systems; EAS reactions, reagents and mechanisms; activation and deactivation; o/p and m directing effects; NAS reactions, reagents and mechanisms; addition and side chain reactions for benzene derivatives.
EXAMINATION 1 (usually after 6 weeks of the semester) (50pts)
Chapter 18 deals with Aldehydes and Ketones; IUPAC naming; syntheses; Nucleophilic addition reactions (both acid and base catalyzed); Wittig reaction; hydration; Relative reactivity; Condensation reactions; imines, acetals, cyclic acetals; use of protecting groups; oxidation; deoxygenation reactions.
Chapter 19 deals with Amines and N containing functional groups; IUPAC naming; Basicity and factors; ammonium salts and their purification; amine (substitution) reactions; nucleophilic acyl substitution yielding amides; Hofmann elimination; Diazonium salt formation and reactions; Syntheses of amines (reductive amination, acylation-reduction, Reduction including azides and nitriles; Hofmann rearrangement, Gabriel synthesis).
EXAMINATION 2 (usually after 10 weeks of the semester) (50pts)
Chapter 20 deals with Carboxylic acids, IUPAC; Ka and pKa values; Syntheses of carboxylic acids; Nucleophilic acyl substitution reactions; Fischer esterification; Acid chlorides preparation and reactions; Diazomethane; Reaction with amines to produce amides; Reduction to aldehydes and alcohols; Conversion to ketones.
Chapter 21 deals with Carboxylic Acids derivatives. Acid halides, anhydrides, esters, amides and nitriles. IUPAC naming of multifunctional molecules; IUPAC of carboxylic derivatives; Relative reactivity towards Nucleophilic acyl substitution, uphill/downhill reactions; effect of an early transition state and leaving group ability in substitution reactions; Acid catalyzed nucleophilic acyl substitutions; Fischer and trans-esterification; Hydrolyses of Carboxylic acid derivatives; Reduction of derivatives; Reactions with organometallics; Functional group summaries.
EXAMINATION 3 (usually last week of classes, after 14 weeks of the semester) (50pts) Often there is a Full Review of the whole semester during the very last lecture period.
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