PRACTICE EXAM QUESTIONS: CARBONYL CHEMISTRY MODULE
Predict the reaction products for the following reactions. You should be able to write
curly-arrow mechanisms for each reaction.
O
Ph
NaOH
(low concentration)
H
+
O
H2 O
Ph
H
O
Ph
H
+
H 2 SO 4
O
H 2O
Ph
H
O
Ph
OH
+
!
H2 C
+
N
N
O
H3C
O
EtO
1) NaOH/H2O
OEt
O
2) HCl
1) NaOEt
OEt 2) CH3 Br /
EtOH
The ketone shown below is subjected to reaction with the amines shown below.
a) Which of the three reactions will give a product with an enamine?
b) Draw the curved arrow mechanism that results in formation of a neutral tetrahedral
intermediate species in the reaction to make an enamine.
c) Why won't the other two amines form an enamine?
d) What will be the outcome of the other two reactions?
H
N
NH2
O
H3 C
heat
H+, H2 O
CH3
N
Match the reactants on the right with the products on the left.
O
O
O
O
+ CH3 OH
O
H2 C
O
OCH3
EtOOC
Ph
COOEt
OH
O
NaOEt
O
O
O
KOH
CH3
heat
EtOOC
H2
C
Ph
EtOOC