Problem_Set_2_Answer_Key

Problem_Set_2_Answer_Key - Organic Chemistry c3046y H+ 1. N...

Info iconThis preview shows pages 1–3. Sign up to view the full content.

View Full Document Right Arrow Icon
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 +
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
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?
Background image of page 2
Image of page 3
This is the end of the preview. Sign up to access the rest of the document.

This homework help was uploaded on 04/16/2008 for the course CHEM C3046 taught by Professor Leighton during the Spring '08 term at Columbia.

Page1 / 3

Problem_Set_2_Answer_Key - Organic Chemistry c3046y H+ 1. N...

This preview shows document pages 1 - 3. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online