9 33 S N 2 The Leaving Group The more stable the anion the better the leaving

9 33 s n 2 the leaving group the more stable the

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9 - 33 S N 2 The Leaving Group The more stable the anion, the better the leaving ability The most stable anions are the conjugate bases of strong acids (a.k.a. halides) I - > Br - > Cl - > H 2 O >> F - > CH 3 CO - > HO - > CH 3 O - > NH 2 - Reactivity as a leaving group Stability of anion; strength of conjugate acid rarely function as leaving groups O Cool manipulation: Good leaving group!
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9 - 34 Structure of R - X (Electrophile) S N 2 reactions: Governed by steric factors Relative ease of approach of a nucleophile to the reaction site Governed by steric factors S N 2 R 3 CX R 2 CHX RCH 2 X CH 3 X Access to the site of reaction (3°) (methyl) (2°) (1°)
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9 - 35 Effect of - Branching 1.2x 10 -5 1.2 x 10 -3 Relative Rate (S N 2) Alkyl Bromide - branches 0 1 2 3 1 0.41 Br Br Br Br Bromoethane (Ethyl bromide) 1-Bromo-2,2-dimethylpropane (Neopentyl bromide)
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9 - 36 Solvents Review Protic solvent: a solvent that is a hydrogen bond donor Many common protic solvents contain -OH groups Aprotic solvent: a solvent that cannot serve as a hydrogen bond donor Nowhere in the molecule is there a hydrogen bonded to an atom of high electronegativity
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