Ochemtest1 - Organic Chemistry II Test 1- February 1, 2008...

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Unformatted text preview: Organic Chemistry II Test 1- February 1, 2008 Chapters 8 & 10 S-Substition N-Nucleophilic 1-Unimolecular 2-Bimolecular SN1 Rate= k[Rx] SN2 Rate= k[Rx][Y:] RX + Y:- RY + X- X-halide F, Cl, Br, I Y- nucleophile Y:- or Y: OH- or H-O-H Rate determining step in SN 2 involves a carbocation All bond breaking and making occurs simultaneously- CONCERTED REACTION R-X + Y:- R-Y + X- X-alkyl halide substrate, Y- nucleophile most often an anion Most frequently used nucleophiles are metal alkoxides (MOR + ) CH 3 O- Na + , CH 3 CH 3 CH 3 O- K, CH 3 CH 2 O- K, Metals consist of Li, Na, and K and ROs consists of alcohol Example Rx: CH 3 CH 2-I + CH 3 CH 2 O- Na CH 3 CH 2-O-CH 2 CH 3 + NaI Carboxylates: CH 3 CH 2-I + CH 3-C-O- CH 3 CH 2-O-C-CH 3 + I- Hydrogen Sulfides: NaSH= Na + :S:--H CH 3 CH 2-I + NaSH CH 3 CH 2-SH + NaI Sulfur Bonds- NaSH; thiols Sulfur bonded compounds M + CN- Cyanides CH 3 CH 2-I + :CN: CH 3 CH 2-CN + I- Loose halogen carbon w/ negative charge attaches Azide N 3- NaN 3 [:N=N=N:]- KN 3 CH 3-CH 2-I CH 3 CH 2-N 3 + NaI R-X leaving group CH 2 CH 3-I CH 3 CH 2-CHCH-Br NR Only sp3 do SN1, SN2 substitution...
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This note was uploaded on 04/17/2008 for the course CHE 240 taught by Professor Hicks during the Spring '08 term at Thomas More KY.

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Ochemtest1 - Organic Chemistry II Test 1- February 1, 2008...

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