PPS 20 solutions - 3 Cl H H 3 CH 2 C Br H Br H Br H Cl H Br...

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C357 PPS#20 Solutions Page 1 of 3 1) Circle the better of each pair of nucleophiles: O - OH O - O - O - S - O O - O - Cl- Br- I- Br- 2) Circle the better of each pair of leaving groups: O O - O - I- Br- Cl- Br- HO- H 2 O 3) Circle the solvents below that would be suitable solvents for the S N 2 reaction: OH OH O O N F F F F F F S O CCl 4 H 2 O
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Page 2 of 3 4) Predict the S N 2 products (if any) of the following reactions and be sure to include stereochemistry where appropriate. Unless otherwise stated, assume NaOH is added in excess. The statement “1 equiv.” means the NaOH is added one to one (equal amounts) with the alkyl halide. CH
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Unformatted text preview: 3 Cl H H 3 CH 2 C Br H Br H Br H Cl H Br H H 3 C H Br H H CH 3 Heat Heat Heat 1 equiv. NaOH Heat 1 equiv. NaOH Heat a) b) c) d) e) CH 3 HO H CH 2 CH 3 H OH H OH H OH Cl H H OH H 3 C H H HO H CH 3 NaOH NaOH NaOH Page 3 of 3 4) Cont from page 2 H Br Heat Br Heat Cl H Heat Br Heat g) h) i) j) Br Heat f) No Sn2, but if allowed to sit, Sn1 will happen and produce these products: HO HO HO H No Reaction of any kind! Why? No Reaction of any kind! Why? H OH NaOH NaOH NaOH NaOH NaOH P.S. E2 could happen as well, but the question is asking about substitution!...
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PPS 20 solutions - 3 Cl H H 3 CH 2 C Br H Br H Br H Cl H Br...

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