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Problem_Set_2_Answer_Key

Problem_Set_2_Answer_Key - Organic Chemistry c3046y H 1 N...

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Organic Chemistry c3046y Problem Set 2 - ANSWER KEY H 2 NCH 3 2. A little less straightforward, this problem illustrates the fact that ketals can exchange to other ketals if treated with H + (NOTE that it is H + , NOT H 3 O + ) and if there is another alcohol around. In this case, the driving force is the simple fact that a 5-membered ring ketal is more stable than an 8-membered ring ketal. In fact, there is also a 7-membered ring ketal that can form, and as long as the acid is around, all 3 of these possible ketals will be in equilibrium with each other. The equilibrium, however, will overwhelming favor the 5-mem. ring. 3. 1. + N CH 3 H + N CH 3 H H 2 O H N OH 2 H 3 C -H + , +H + N OH H 3 C H H O H O Hopefully very straightforward. O O Me Me HO H + O O Me Me OH O O Me Me HO H O HO OH Me Me O O Me Me OH H H + Ph CH 3 OH H + O H + Ph CH 3 HO O Ph CH 3 O O Ph CH 3 O O H +
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4. ? O O Et Me exo -Brevicomin OH Et OH O O Et Me HO HO Et O Me That stuff I wrote in italics above? Important. What is the product? It's a ketal. How are ketals made?
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