This preview shows page 1. Sign up to view the full content.
Unformatted text preview: C C CH 3 CH 3 H H H OH View TURN TURN TURN: Using the view of the bond indicated, draw the major 6 Newman projections by rotating the front carbon 60 clockwise. Circle the most stable conformation, put a square around the least stable conformation. HO CH 3 H H CH 3 H HO CH 3 H H H H 3 C HO CH 3 H CH 3 H H HO CH 3 H H H H 3 C Note the chiral center - this configuration must be preserved in your Newmans, otherwise you have changed the molecule check your drawings: have you rotated (good) or flipped (Bad)?! HO CH 3 H CH 3 H H HO CH 3 H H CH 3 H It is fairly obvious that the OH is less of a steric issue than the CH 3 groups (O is like the skinny guy, doesn't even have a fat head - think of -OCH 3 for skinny with fat head!) the O has two lone pairs and only an H, while the methyl group has 3 Hs attached in the same space. The most stable HAS to be a staggered: the methyls are bigger, so it is more important that they are anti. Note the other two staggered conformers: both has methyl-methyl gauche interaction, but the top right ALSO has methyl and OH gauche more...
View Full Document
This note was uploaded on 01/28/2011 for the course CHEM 215 taught by Professor Koreeda during the Spring '07 term at University of Michigan.
- Spring '07