Haloalkanes, Alcohols and Amines. Year 1 Dr

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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..

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Chapter 7, Haloalkanes, Properties and Substitution Reactions of Haloalkanes Table of Contents 1
Chapter 7, Haloalkanes, Properties and Substitution Reactions of Haloalkanes Table of Contents 1. Alkyl Halides (Haloalkane) 2. Nucleophilic Substitution Reactions (SNX, X=1 or 2) 3. Nucleophiles (Acid-Base Chemistry, pka) 4. Leaving Groups (Acid-Base Chemistry, pka) 5. Kinetics of a Nucleophilic Substitution Reaction: An SN2 Reaction 6. A Mechanism for the SN2 Reaction 7. The Stereochemistry of SN2 Reactions 8. A Mechanism for the SN1 Reaction 9. Carbocations, SN1, E1 10. Stereochemistry of SN1 Reactions 11. Factors Affecting the Rates of SN1 and SN2 Reactions 12. --Eliminations, E1 and E2 13. E2 and E1 mechanisms and product predictions In this chapter we will consider: What groups can be replaced (i.e., substituted) or eliminated The various mechanisms by which such processes occur The conditions that can promote such reactions Alkyl Halides (Haloalkane) An alkyl halide has a halogen atom bonded to an sp3-hybridized (tetrahedral) carbon atom The carbon–chlorine and carbon– bromine bonds are polarized because the halogen is more electronegative than carbon The carbon-iodine bond do not have a per- manent dipole, the bond is easily polarizable Iodine is a good leaving group due to its polarizability, i.e. its ability to stabilize a charge due to its large atomic size Generally, a carbon-halogen bond is polar with a partial positive () charge on the carbon and partial negative () charge on the halogen C X X = Cl, Br, I Different Types of Organic Halides Alkyl halides (haloalkanes) sp3-hybridized Attached to Attached to Attached
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Classifying Halogenoalkanes Reactions Of
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Generic Functional Group Pattern in Ordero of Nomenclature Priority in Our Course. Specific Example Using Suffix (2D and 3D)
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A Perovskite-Based Paper Microfluidic Sensor for Haloalkane Assays
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Fully Halogenated Chlorofluorocarbons
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Haloalkanes and Haloarenes
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91165 Organic Chemistry Cornell Notes
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Chapter 7: Haloalkanes
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