PPS 21 solutions - 5) Answers continued from page 3. H +...

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C357 PPS#21 Solutions Page 1 of 6 1) Propose a mechanism to account for the formation of the following reaction products. Cl CH 3 CH 2 CH 3 H CH 3 CH 2 CH 3 H + or H 3 CO CH 3 CH 2 CH 3 H OCH 3 CH 3 H 3 CH 2 C H H H + + H 3 CO CH 3 CH 2 CH 3 H OCH 3 CH 3 H 3 CH 2 C H CH 3 OH CH 3 OH CH 3 OH 2) Propose a mechanism to account for the following reaction products. OH Br OH + OR OH + OH OCH 3 H + OH OCH 3 O H + O CH 3 OH CH 3 OH CH 3 OH
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Page 2 of 6 3) Propose a mechanism to account for the following reaction product. Br H 3 C H 3 C + H 3 C + H 3 C OCH 3 H + H 3 C OCH 3 CH 3 OH CH 3 OH 4) Propose a mechanism to account for the following reaction products. Br H 3 C CH 3 H 3 C CH 3 + OR H 3 C CH 3 H + H 3 C CH 3 H + H 3 C CH 3 O CH 3 CH 3 H H + H 2 O HO CH 3 CH 3 H 2 O H 2 O
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Page 3 of 6 5) Draw and circle all of the SN1 and E1 products you expect from the following reaction. Br H H + 2 o Carbocation can rearrange to two different 3 o carbocations H + H + H H 3 o carbocation 3 o carbocation Cation A Cation B Cation C Cations A, B, and C can result in products. See the following pages for products from each cation.
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Unformatted text preview: 5) Answers continued from page 3. H + Cation A H H HO OH E1 H H H 1 2 3 4 5 Sn1 H + H 3 o carbocation Cation B H H HO 6 E1 H H 7 H Same as #3 Sn1 Continued on page 5 Page 5 of 6 5) Continued from page 4 H + H 3 o carbocation Cation C H H H H HO HO 8 9 E1 H H Same as #5 Same as #4 H H H 10 H H H 11 CH 3 H H H H H H H 3 C 12 13 Sn1 End of problem #5 Page 6 of 6 6) Propose a mechanism to account for the following reaction product. Br + + O H H + OH H 2 O H 2 O 7) Propose a mechanism to account for the following reaction products. Br H CH 3 H CH 3 + OR H CH 3 + H CH 3 + OR or H 3 CO H CH 3 H CH 3 O CH 3 H H + + H OCH 3 CH 3 H 3 CO H CH 3 H H H H CH 3 CH 3 CH 3 OH CH 3 OH CH 3 OH CH 3 OH CH 3 OH...
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PPS 21 solutions - 5) Answers continued from page 3. H +...

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