ch 22:

Question 1

what is an alpha carbon?

Answer 1

the carbon next to the carbonyl carbon

Question 2

is the alpha carbon nucleophilic or electrophilic?

Answer 2

nucleophilic
- reacts with carbonyl carbon

Question 3

enol form

Answer 3

C=C and OH instead of C=O
- enol and keto are tautomers
- ALPHA H IS MOVING FROM ALPHA CARBON TO CARBONYL

Question 4

tautomers

Answer 4

isomers that are in equilibrium with each other
- constitutional isomers

Question 5

is the keto or enol form favored?

Answer 5

keto form because C=O is stronger than C=C

Question 6

what is needed for an enol to form?

Answer 6

alpha carbon with alpha hydrogen

Question 7

if the ketone is unsymmetrical, how many enols are possible?

Answer 7

two

Question 8

KNOW ACID CATALYZED TAUTOMERIZATION

Answer 8

carbonyl protonates itself which breaks C=O, forming carbocation
acid attacks alpha H which creates C=C

Question 9

KNOW BASE CATALYZED TAUTOMERIZATION

Answer 9

base attacks alpha hydrogren forming a negative on the alpha carbon
alpha carbon forms C=C breaking C=O
oxyanion protonates itself