Substitution Reaction Practice answers

Substitution Reaction Practice answers - DMF S N 2 DMSO S N...

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Substitution Reactions Chemistry 14D – Gould Instructions: For each of the following reactions determine if the reaction proceeds via a S N 2 or S N 1 mechanism. Draw the major product(s). Provide a reasonable solvent for each reaction try not to use the same solvent more than 3 times. Draw the full mechanism for two (2) S N 2 reactions and two (2) S N 1 reactions. Br Br Br Br Br Br NaOH H 2 O NaOCH 3 CH 3 OH NaI NaOCH 3 OH OH OCH 3 OCH 3 I OCH 3 Acetonitrile S N 2 (shown) or S N 1 depending on Solvent choice; if S N 1 watch out for rearrangement S N 1 Water is a good solvent and nucleophile in this case
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Unformatted text preview: DMF S N 2 DMSO S N 1 S N 2 Methanol is a good solvent and nucleophile in this case Acetone S N 2 Compare your mechanisms to the mechanisms in the notes or text. Br OTs I Br Br OTs CH 3 OH CH 3 Li H 2 O NaI CH 3 SH H 2 O OCH 3 CH 3 OH I SCH 3 OH S N 1 DMF Methanol S N 1 S N 2 S N 1 Methanol is a good solvent and nucleophile in this case Acetone Water is a good solvent and nucleophile in this case S N 2 (shown) or S N 1 depending on Solvent choice S N 1 Water is a good solvent and nucleophile in this case...
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This note was uploaded on 08/20/2008 for the course CHEM 14D taught by Professor Hardinger during the Spring '08 term at UCLA.

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Substitution Reaction Practice answers - DMF S N 2 DMSO S N...

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