Ch 7 Halides - R-OH R ʼ S-sulfide R-SR ʼ R ʼ-O(alkoxide ether R-O-R ʼ NH 3 amine NH 3 R-NH 2 H-O-R ʼ ether R-O-R ʼ H-O-H alcohol

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Haloalkanes Nomenclature - Halogens are designated by bromo, chloro, fluoro and iodo in alphabetical order with other alkyl substituents. - They are numbered according to the substituent encountered first. - The suffix and numbering are determined by the functional group.
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S N 2 Reaction - a single step reaction - 2 reactants (nucleophile + alkyl halide) lead to a transition state - backside attack - single transition state ie. no intermediate - Rate = k [R-X][Nuc] - inversion of configuration - methyl > 1 ° >2 ° >>3 °
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S N 1 Reaction - unimolecular nucleophilic substitution - one reactant leads to an intermediate - carbocation intermediate - Rate = k [R-X] - product is a racemic mix - 3 ° > 2 ° >> 1 ° or Me - often solvolysis = solvent is reactant
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Nucleophiles Product best Cl - , Br - , I - alkyl halide R-X SH - thiol R-SH OH - alcohol
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Unformatted text preview: R-OH R ʼ S-sulfide R-SR ʼ R ʼ-O-(alkoxide) ether R-O-R ʼ NH 3 amine NH 3 + ! R-NH 2 H-O-R ʼ ether R-O-R ʼ H-O-H alcohol R-O-H -charged species > lone pairs > water, alcohol best worst Elimination Reactions (often occur with S N 1 or S N 2 reactions) Alkyl halide + strong base ! alkene A strong base can also be a nucleophile so elimination reactions can compete with S n 1 and S N 2 reactions. E2 - 2 species transition state - one step reaction - concerted E1 - one species as intermediate - carbocation is formed (as in S N 1) - 3 ° carbocation > 2 ° carbocation > 1 ° carbocation >> methyl - usually a mix of S N 1 and E1 products ** S N 2 and E2 ; S N 1 and E1 reactions can compete ! a mix of products especially for 2 ° alkyl halides ** Remember that Zaitsev ʼ s rule applies...
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This note was uploaded on 03/01/2010 for the course CHEM 1570 taught by Professor Usher, d during the Spring '08 term at Cornell University (Engineering School).

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Ch 7 Halides - R-OH R ʼ S-sulfide R-SR ʼ R ʼ-O(alkoxide ether R-O-R ʼ NH 3 amine NH 3 R-NH 2 H-O-R ʼ ether R-O-R ʼ H-O-H alcohol

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