CHEM 102 Lecture Notes - Lecture 5: Amine, Phenyl Group, Triethylamine

• School: BRCC
• Department: CHEM - Chemistry
• Course: CHEM 102
• Professor: Larry Dalton

Document Summary

We consider a reaction that at first sight seems to go against what we have told you so far. It"s an elimination catalysed by a strong base (koh), so it looks like e2. But the leaving group is hydroxide, which we categorically stated cannot be a leaving group in e2 eliminations. The key to what is going on is the carbonyl group. Negative charges are stabilized by conjugation with carbonyl groups, and the table on p. 000 demonstrated how acidic a proton adjacent to a carbonyl group is. The proton that is removed in this elimination reaction is adjacent to the carbonyl group, and is therefore also rather acidic (pka about 20). This means that the base can remove it without the leaving group departing at the same time the anion that results is stable enough to exist because it can be delocalized on to the carbonyl group.