Answers to Problem 56, Chemistry 226 - 2022

O
Pr
Et KOH/H2O Ketone 1 has no acidic protons. Therefore, it
Ph maintains its optical activity because it cannot
or H3O+ undergo a keto/enol tautomerization.
Me
1

Me O
Pr
KOH/H2O Ketone 2 has acidic protons. However,
keto/enol tautomerization does not change the
Ph stereochemistry (maintains optical activity)
Et or H3O+ because the acidic protons are not attatched to
2 the stereogenic carbon.

O
Me
O O
Et KOH/H2O
Ph Me Et
or H3O+ Et Me
H Ph Ph
+
3
H H

Racemate

Ketone 3 has an acidic proton attached to the

stereogenic carbon. Therefore, keto/enol
tautomerization will result in a scrambling of
stereochemistry & result in a loss of optical
activity.