problem set 6 key - orgo

problem set 6 key - orgo - c) O HO O O Br H H Br 2 H 2 O O...

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Monday Night Problem Set 6 Chemistry 221 1. Complete the following reactions. Show stereochemistry , where appropriate. H 2 Pd/C Br 2 H 2 O KMnO 4 OH H H syn addition hydrobromination, -OH goes markovnikov -Br goes antimarkovnikov OH Br oxidative cleavage O OH O cyclopropanation CH 2 I 2 Zn/Cu Antimarkovnikov hydration= hydroboration BH 3 , NaOH H 2 O 2
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2. Propose a mechanism for each of the following reactions: H 2 SO 4 a) OH O H 2 SO 4 H 2 O OH b) H + OH H + OH O H - H + product OH 2 OH 2 - H + product this is a pretty standard Markovnivkov addtion of H 2 O This mechanism is analogous to the one in part a), though the alcohol acts as an internal nucleophile!
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Unformatted text preview: c) O HO O O Br H H Br 2 H 2 O O HO Br-Br O HO Br O O Br H H O O Br H H H- H + 3. Show the starting material for each of the following reactions: O O O 3 Zn Br Br Br 2 CCl 4 The carbons with the carbonyl groups were formerly doubly bound to each other Careful, since Br 2 adds anti, sterochemistry is important rotate Br Br 4. Draw the organic product for this acid base reaction between propyne and sodium amide (a very powerful base). H H 3 C + NaNH 2 H 3 C...
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This note was uploaded on 04/29/2008 for the course CHEM 221 taught by Professor Fillinger during the Spring '08 term at Ithaca College.

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problem set 6 key - orgo - c) O HO O O Br H H Br 2 H 2 O O...

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