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Organic Chemistry Supplement: Alkyl Halides Reactions in Nucleophiles' Realm

Learn how alkyl halides react with nucleophiles and bases in this organic chemistry supplement. Discover the polarized nature of carbon-halide bonds, leading to electrophilic carbon. Explore SN2 reaction kinetics, stereochemistry, and biological substitution reactions. Unveil the E2 reaction and deuterium isotope effect for alkene formation. Dive into the world of organic chemistry with insights on biological substitutions and the significance in ATP phosphoanhydride bonds.

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Organic Chemistry Supplement: Alkyl Halides Reactions in Nucleophiles' Realm

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  1. Organic Chemistry SupplementAlkyl Halides React with Nucleophiles and Bases • Alkyl halides are polarized at the carbon-halide bond, making the carbon electrophilic • Nucleophiles will replace the halide in C-X bonds of many alkyl halides(reaction as Lewis base) • Nucleophiles that are Brønsted bases produce elimination

  2. 11.2 The SN2 Reaction • Reaction is with inversion at reacting center • Follows second order reaction kinetics • Ingold nomenclature to describe characteristic step: • S=substitution • N (subscript) = nucleophilic • 2 = both nucleophile and substrate in characteristic step (bimolecular)

  3. SN2 Transition State • The transition state of an SN2 reaction has a planar arrangement of the carbon atom and the remaining three groups

  4. Stereochemistry of SN1 Reaction • The planar intermediate leads to loss of chirality • A free carbocation is achiral • Product is racemic or has some inversion

  5. 11.6 Biological Substitution Reactions • SN1 and SN2 reactions are well known in biological chemistry • Unlike what happens in the laboratory, substrate in biological substitutions is often organodiphosphate rather than an alkyl halide

  6. 11.8 The E2 Reaction and the Deuterium Isotope Effect • A proton is transferred to base as leaving group begins to depart • Transition state combines leaving of X and transfer of H • Product alkene forms stereospecifically

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  8. This can be extended to Phosphoanhydride bonds found in ATP 5

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