10 - Br I e) Fastest S N 1 reaction Br NaI acetone NaI...

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Br Br H Br TsO Br I Br Br Br OH H I Chem 212 Alkyl Halide Problems 2 1. Provide the products, reagents or starting materials needed for the following reactions, show all stereochemistry. 2. Identify whether the reaction goes by an S N 2 or an S N 1 mechanism. NaI acetone Cl a) b) NaN 3 DMSO Cl c) I d) NaCN DMF H Br H Br NaBr acetone e) NaBr H 2 O f) g) h) NaBr H 2 O O I) NaI H 2 O j) Br H 2 O Br k) Br NaCN DMSO l) Br NaBr H 2 O Br Br m) n) NaBr acetone o) Br MeOH I p) Br 3. Give the indicated rankings for the following. Provide explainations for your rankings I a) Fastest S N 2 reaction with NaI in acetone OH O b) Fastest S N 1 reaction with NaI in water c) fastest S N 2 reaction Br NaI acetone d) best solvent for a S N 2 reaction I NaI hexane
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Unformatted text preview: Br I e) Fastest S N 1 reaction Br NaI acetone NaI water Br f) fastest S N 1 reaction NaI water Cl Br I NaI water g) fastest reaction with NaSH h) best Nucleophile NaCN NaOH NaBr i) best nucleophile NaI NaBr NaF Br OH Br NaH NaI acetone S N 2 I N 3 H CN OMs Br OTs S N 2 S N 2 S N 1 S N 1 S N 1 S N 2 S N 2 H 2 O NaI H 2 O S N 1 I S N 1 + S N 1 Br NC H Br S N 2 S N 1 S N 1 OMe I TsO OH S N 2 H MsO H OMs slowest best best slowest faster slower faster fastest fastest slowest faster slower worst fastest slower about the same best...
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