QO-IV Problems 3b

1. Indicate the reaction products

a. Pentanal + potassium hydroxide (water 0º)
b. Octanal + sodium ethoxide (ethanol, reflux)
c. Acetone + barium hydroxide (water r.t.)
d. Acetone + Dowex-50 (water, refux)
e. Methyl t-butyl ketone + benzaldehyde + sodium hydroxide (ethanol, reflux)
f. Acetone + benzaldehyde + `potassium hydroxide (ethanol, r.t.)
g. 3-pentanone + phthalaldehyde+ sodium ethoxide
2. Complete the following reactions
1. LDA
2. MeI
O
O
LDA allyl bromide
25º
THF -78º

ethylene
LDA oxide
MeCN

O O LDA LDA
(1 eq.) (1 eq.) 1. Et-I
Ph CH3
2. H2O
3. Propose a synthesis for
O O
OH O
O O NH 2

Br
meparfynol

HO
CO2H
HO
4. The following compounds are produced through a Michael reaction, indicate the
starting materials
O
a c d
NC CONH2 b Ph CO 2Et
O2N
Ph CO2Et
CO2Me MeO2C CO2Et CO2Et
CO2Me
e O h CO2Et
O f g

O O
O O
5. Draw the main disconnection for these molecules
O
a CO2Et b OH c OH
CHO
O O O
O
O
Cl Cl
QO-IV Problems 3b

6. Propose a synthesis for the heterocyclic compound

O
N
O
7. Explain the reactions implied in the following process
OH
CH2O
CHO
NaOH OH
8. Indicate a possible synthesis for the acetal
O C7H15

9. Explain the selectivity in the next reactions

O O
a PhCHO + OH KOH
Ph CO2H
O
O O
OHC
b
KOH
O O

c NaH
CO(OMe)2
O O

CO2Me
10. Predict the only condensation product formed in each transformation
a. 1-phenyl-1,4-pentanodione + NaOH
b. Isopropyl methyl ketone + base
O
O
+ Py
N CHO O AcOH
c. O