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CHEM 316 problem%20set%207.006%20solutions

CHEM 316 problem%20set%207.006%20solutions - Problem Set 7...

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O O O C N O O N O N O C Br O NH F I Cl Br N(CH 3 ) 2 OCH 3 F I Cl Br N(CH 3 ) 2 OCH 3 1. Identify sites in each molecule that can act as nucleophiles and electrophiles. 2. Rank each of the following sets of reactive intermediates from most to least stable: set 1: set 2: set 3: set 4: set 5: set 6: Problem Set 7 Solutions Chem 316 1 2 3 4 1 2 3 4 4 2 1 3 1 2 3 4 5 6 7 1 2 3 4 5 6 H 7 O 1 O H 2 3 H 4 O H 5 6 : nucleophiles : electrophiles These are ordered from most stable (1) to least stable. Some of the values in set 5 are arguable without concrete electronegativity data.
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Br - Br - doesn't form because the intermediate would be a 1˚ carbocation and not resonance-stabilized (very unstable carbocation) H + Br - Br Br Br Br - OH Br - major isomer: comes from more stable carbocation 3. Show the electron flow (add the appropriate arrows and any missing intermediates) to show the mechanisms for the following reactions. Classify each reaction as an addition, elimination, or substitution.
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