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

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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
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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 + :CΞN: CH 3 CH 2 -CΞN + 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 -CHΞCH-Br NR Only sp3 do SN1, SN2 substitution Factor controlling substitution rate R-X + Y: - RY + :X: - , alkyl halides- X
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