Dolbier HW Solutions 432

Dolbier HW Solutions 432 - 526 CARBOXYLIC ACIDS (b) As in...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
( b ) As in part ( a ), lactone formation is possible only when the hydroxyl and carboxyl groups are cis. Although the most stable conformation of cis -3-hydroxycyclohexanecarboxylic acid has both substituents equatorial and is unable to close to a lactone, the diaxial orientation is accessible and is capable of lactone formation. Neither conformation of trans -3-hydroxycyclohexanecarboxylic acid has the substituents close enough to each other to form an unstrained lactone. 19.25 ( a ) The most stable conformation of formic acid is the one that has both hydrogens anti. A plausible explanation is that the syn conformation is destabilized by lone-pair repulsions. ( b ) A dipole moment of zero can mean that the molecule has a center of symmetry. One structure
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 09/30/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

Ask a homework question - tutors are online