This preview shows page 1. Sign up to view the full content.
Unformatted text preview: Please explain your reasoning clearly and concisely. * * * N O O O N O O H H H H H H N O O O N O O H H H H H H This one is likely to contribute less, since charge is more separated (including a formal positive charge on a very electronegative oxygen). carboxylic acid tetrahedral, sp 3 trigonal planar, sp 2 The proton that is part of the lefthand carboxylic acid is most likely to be removed. This proton is attached to an oxygen atom, the most electronegative type of atom in carbaglu. The electron density left behind upon deprotonation is delocalized (stabilized) via resonance with the attached carbonyl and inductively by the electronegative carbonyl oxygen and the nearby NHR group. Note that this NHR group is closer to the lefthand COOH group than it is to the righthand one....
View Full Document
- Spring '10