13 - Chem 10172, Spring 2008 PROBLEM SET 13 SOLUTIONS Due...

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Chem 10172, Spring 2008 PROBLEM SET 13 SOLUTIONS Due Tuesday, April 29 1 Problems for Discussion: (1) Remember that syntheses may have many possible good solutions (alas, they also have many possible bad solutions as well), so if your answer differs from the one given it may be quite acceptable. (e) H NaNH 2 C C CH 3 I Na NH 3 (liq.) (f) H Br 2 CH 2 Cl 2 Br Br NaO t Bu (2 equiv) BuOH Note that the geometry of the dibromide ensures elimination of the proper hydrogens: Br Br H H H only these H's are anti-periplanar to the Br's and will be eliminated in this E2 reaction these H's cannot become anti-periplanar (g) Br 1) BH 3 2) H 2 O 2 , OH OH HBr (2) More butadiene brouhaha. When butadiene is stirred with bromine in cold methanol, four products are obtained, as shown below. Br 2 /CH 3 OH -15˚ C Br OCH 3 Br Br Br Br Br OCH 3 A (63%) D (4%) C (10%) B (22%) (a) Br Br Br H OCH 3 Br O CH 3 H Br Br OCH 3 (b) Br Br Br Br Br Br Br Br (c) At 60 ºC, carbocation formation would be expected to be somewhat reversible, so the
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This note was uploaded on 05/18/2008 for the course CHEM 10172 taught by Professor Brown during the Spring '08 term at Notre Dame.

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13 - Chem 10172, Spring 2008 PROBLEM SET 13 SOLUTIONS Due...

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