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Synthesis of Dibenzalacetone

Purpose: To synthesize dibenzalacetone via an Aldol condensation reaction


(See Handout for mechanism)
Reaction Equation
O
CH
O

O
NaOH

H3C

CH3

H
C

H
C

H
C

H
C

Materials:
Apparatus
Vacuum Filter
Melting point thermometer

H2O

Chemicals
Benzaldehyde Acetone
C7H6O
C3H6O

Molar
Mass
(g/mol)
BP (C)
MP(C)
Density
(g/ml)
Solubility

Sodium
Ethanol
Hydroxide C2H6O
NaOH

Dibenzalacetone/
Dibenzylideneacetone
C17H14O

106.12

58.08

39.9971

46.07

234.292

178.1
57.12
1.044

57
93
0.791

1,388
318
2.13

78.37
114
0.789

130
112
1.1

In ammonia

In water

Polar
solvents
1.357

Polar solvents
1.361

Soluble in nonpolar
solvents
1.649

Wikipedia

Chemnet.com

Refractive 1.545
Index (nD)
Reference Wikipedia

1.359

Wikipedia Wikipedia

Pre Laboratory Questions:


1. Write a mechanism for the formation of benzalacetone from acetone and
benzaldehyde.
2. Why did you use specific quantities of reagents that are called for in the synthesis
of dibenzylacetone?
OH is known to yield the enolate, which we must generate from acetone, in small
amounts. So we must add more than a 1:1 ratio of acetone and sodium hydroxide
in order to generate more enolate. I chose to add a molar ratio of acetone to
sodium hydroxide 10:1 which calls for me to add .0625g acetone.
3. In principle, both cis and trans dibenzalacetone can form. How could you use
proton NMR to distinguish between cis-cis and trans-trans?
The trans isomer will show doublets with a higher coupling constant.

4. Identify each of the attached spectra as benzaldehyde, acetone or


dibenzalacetone.
Procedure

Observations

Procedure:
1. Weigh out 0.265g of benzaldehyde
and a theoretical quantity of
acetone. Calculate the theoretical
quantity of acetone before you
arrive for lab!
2. Add the correct quantities of these
reagents together. (Use the Rainin
pipet to dispense the correct amount
of acetone in microliters.)
3. Dissolve 0.25g of NaOH in 2.5 mL
of water, then add 2.0mL of
ethanol.
4. Cool the hydroxide solution to
room temperature.
5. Add one-half of your
benzaldehyde-acetone mixture to
the hydroxide solution.
6. After about 15min. add the
remainder of this mixture.
7. Rinse the container with a small
amount of ethanol and add this to
the reaction mixture.
8. Swirl occasionally for 30 min.
9. Stir with a stirring rod to allow the
precipitate to break up and
crystallize.
10. Collect the product by.
11. Wash the crystals with 5mL of
water three times to remove any
NaOH.
12. Recrystallize from 95% ethanol
using 2.5mL per gram of product.
13. Check the melting point of the
recrystallized product (110 o to 111o
C).

Acetone is very volatile so reaction must be


capped
Theoretical quantity of acetone is .092ml
Volume of benzaldehyde is 0.254ml
When we mixed the benzaldehyde acetone
solution with the NaOH solution, the
solution turned clear yellow to an opaque
yellow.

Dibenzalacetone Data Table

gm Benzaldehyde:________0.265_______ mol Benzaldehyde:______.0025______

Moles Acetone__.00136____
gm Acetone:____.07277_______
L Acetone:______________
Theoretical Yield (moles)_____.00136______
Theoretical Yield (grams):___.3186_____
Actual yield of recrystallized product:__.2314.3186100 = 72.6_________
Percent Yield:_____72.6%__________
Melting point of recrystallized product:______111.7____________
Conclusion
We were able to successfully synthesize DNB via an aldol mechanism. We got a high
yield due to the equilibrium being pushed to the right throughout the experiment. This
crossed aldol reaction is considered synthetically useful because the structure of the
reagents permitted only one molecule to exclusively be converted to enolate.

Dibenzalacetone

Acetone

See chemical shift


assignments in the
Table below.

Dibenzalacetone