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Problems 3 B

This document outlines 10 chemistry problems involving reactions such as aldol condensations, Michael additions, and heterocycle syntheses. It asks the reader to identify reaction products, propose syntheses, and predict selectivity in various condensation reactions. Key reactions mentioned include Grignard, Wittig, aldol, Michael addition, and heterocycle formation.

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100 views

Problems 3 B

This document outlines 10 chemistry problems involving reactions such as aldol condensations, Michael additions, and heterocycle syntheses. It asks the reader to identify reaction products, propose syntheses, and predict selectivity in various condensation reactions. Key reactions mentioned include Grignard, Wittig, aldol, Michael addition, and heterocycle formation.

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Lng
Copyright
© © All Rights Reserved
Available Formats
Download as PDF, TXT or read online on Scribd
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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

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