Haloalkanes, Alcohols and Amines. Year 1 Dr. Chris Braddock [[email protected], Rm 440]: 10 lectures Aims of course: To introduce the functional group chemistry of haloalkanes, alcohols and amines, building on the functional group approach of Dr Smith's course where alkanes, alkenes, alkynes and benzene were discussed. Course objectives: At the end of this course you should be able to: • Identify correctly the various functional groups and reagents introduced on this course; • Recognise characteristic IR and NMR signals in their spectra; • Predict the product of a reaction involving an haloalkane, alcohol or amine with a given reagent; • Select reagents for the common transformations of haloalkanes, alcohols and amines into other functionalities; • Select reagents for the preparation of haloalkanes, alcohols and amines from other substrates; • Explain the mechanistic rationale underpinning the above. Recommended Texts Vollhardt and Schore, Organic Chemistry, 3rd edition, WH Freeman & Co, New York, 1999. Sykes A Primer to Mechanism in Organic Chemistry Longman, Harlow, 1995 Clayden, Greeves, Warren and Wothers Organic Chemistry OUP, Oxford 2001. Course Content A. Haloalkane Group Chemistry (Alkyl Halides) (a) Structure and Physical Properties: nomenclature; physical properties; spectroscopic properties. β (b) Haloalkane group reactivity: Nucleophilic substitution S N1 and SN2; - elimination; metal-halogen exchange. (c) Synthesis of haloalkanes: electrophilic addition to alkenes; radical addition to alkenes; from alcohols. B. Hydroxyl Group Chemistry (Alcohols) (a) Structure and Physical Properties: Structure; H-bonding; spectroscopic properties . (b) Alcohol group reactivity: Hydroxyl group acidity; Nucleophilic reactions of hydroxyl groups without C-O cleavage; nucleophilic reactions of hydroxyl groups which convert the OH into a good leaving group; nucleophilic reactions of hydroxyl groups which place a good leaving group on oxygen. (c) Synthesis of alcohols: from carbonyls via disconnection approach; from alkenes; by nucleophilic substitution. C. Amine Group Chemistry (a) Structure and Physical Properties: Structure; spectroscopic properties; basicity – comparison with alcohols (b) Amine group reactivity: with haloalkanes – (over)alkylation; with carbonyl groups – imine formation; with acid chlorides – amide fromation (c) Synthesis of amines: alkylation; Gabriel synthesis; reductive amination; from amides..