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Introduction to Organic Chemistry

Prof. S. Connon (28 lectures)

This introductory course on organic chemistry covers the structures and properties of compounds containing the common functional groups. Strong emphasis is placed on a mechanistic understanding of the chemistry involved, rather than on rote learning functional group chemistry.

Topics dealt with include:

Alkanes, isomers, homologous series, IUPAC nomenclature, physical properties and molecular size, the tetrahedral carbon atom, shapes of organic molecules, alicyclic rings, concept of bond strain, conformations of ethane and of the cyclohexane ring, chair and boat forms and their relative stabilities, axial and equatorial bonds.

Alkyl halides, idea of leaving group, introduction to the use of curly arrows in representing mechanism, idea of nucleophiles and electrophiles, nucleophilic substitutions, SN1 and SN2 mechanisms, carbocations, dehydrohalogenation, elimination mechanisms E1 and E2 emphasising common intermediate for SN1 and E1, direction of elimination, Saytzeff rule, organo lithium and Grignard reagents as carbon nucleophiles.

Alcohols, hydrogen bonds, differences between primary secondary and tertiary, amphoteric nature of the OH group, alkoxides, mechanism of dehydration, oxidation.

Alkenes, nomenclature, the double bond as an electron rich centre mechanism of electrophilic addition of hydrogen halides, water, and halogens to the double bond, Markownikoff rule, shape of the double bond, geometric isomerism, cis-trans isomers and E-Z nomenclature, catalytic hydrogenation, oxidative cleavage of double bond including ozonolysis.

Alkyne reactions treated briefly as a simple extension of alkene reactions, acidity of alkynes and nucleophilic character of the alkyne anion.

Amines as bases and as nucleophiles.

Aldehydes and ketones, nucleophilic attack on the carbonyl carbon, cyanohydrins, oximes, hydrazones, Grignard products, acetals and the mechanism of their formation, oxidation and reduction of the carbonyl group, keto-enol tautomerism, the enolate anion, resonance, haloform reaction, aldol condensation.

Carboxylic acids, acid strength, carboxylate anions, esters, acid halides, acid anhydrides, amides, emphasis on electrophilic nature of carbonyl group, mechanism of esterification and hydrolysis.

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