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PPS 23 solutions - N 1 reaction B C E c The starting...

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C357 PPS#23 Solutions Page 1 of 6 1) Li H H Br H Na H 2 O H 2 SO 4 NH3 (l) 1) O 3 2) (CH 3 ) 2 S + H H OH O - Na+ O H H H O O H H O H
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Page 2 of 6 2) Br O H O H N Br - O O H Br O H O H Br O O H O H O H N Br O O H O H O - Br O H O H Br O O H O H O O H O H N Br O O H O H O O - O H Br O H O H Br O O H O H O O O H O H O H N Br O O H O H O O O H - O O O H O H O O O H O
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Page 3 of 6 3) Br H NaOH OH H 4) C + H C + H C + H C + H C + H C + H C + H
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Page 4 of 6 5) A) F B) F C) T D) T E) F F) T 6) H 3 C H H 3 C H H 3 C H Chiral Achiral Chiral 7) CH 3 Br D H 2 O Heat D OH CH 3 C + CH 3 D C + CH 3 D H O H CH 3 D O + H H H O H
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Page 5 of 6 8) Chiral Chiral Achiral Achiral Achiral Product A Product B Product C Product D Product E O CH 3 OH H HO H H OH H H OH H H OH H H 9) a) The starting material(s) that would produce a single alkene product in an E2 elimination. A, B b) The starting material(s) that would likely undergo rearrangement in an E1 or S
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Unformatted text preview: N 1 reaction. B, C, E c) The starting material(s) that could undergo an S N 2 reaction but could not undergo an E2 elimination. E d) The starting material(s) that would likely NOT undergo rearrangement in an E1 or S N 1 reaction (yet could undergo the reactions). A, D e) The starting material(s) that would undergo the most rapid E2 elimination. D Page 6 of 6 10) Br ONa OH H 11) H H CH 3 H 3 C H H...
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