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As illustrated for the reaction of benzaldehyde with a general ketone, the ketone looses a proton from
an -carbon to form an enolate ion, which attacks the carbonyl carbon of the aldehyde to yield, after
protonation, a -hydroxy ketone. This intermediate is, for aromatic aldehydes at least, instable and
undergoes base-catalyzed dehydration to yield the unsaturated product.
OBJECTIVE:
PROCEDURE
1. 0.75g of 3-nitrobenzaldehyde was weigh and was placed in 50ml Erlenmayer flask
2. 0.60ml of acetophenone and 4.0ml of 95% ethanol was added to the flask containing the
aldehyde
3. The flask was swirled to mix the reagent and any solids was dissolved. The solution was cooled
at room temperature.
4. 0.5 ml of NaOH solution was added. The mixture was stirred until it solidified.
5. 10ml of ice water was added to the flask.
6. The mixture was transferred to a beaker with 15ml of water.
7. The solid was collected by vacuum filtration on a bunchner funnel. The solid was washed with
cold water and was allowed it to dry for 30 minutes.
8. The solid was weighed and the crude percent yield was determined.
9. 0.5 g of solid from 20ml of hot methanol was recrystallized. The solid was collected by vacuum
filtration and was dry it in the oven.
10. The dry pure product was weight and the percent yield was determined
11. The melting point was measured and a proton NMR spectrum of the product obtained.
RESULT
Mass of 3-nitrobenzaldehyde
Mass of crude product
Melting point
CALCULATION
Mass of 3-nitrobenzaldehyde = 0.7489g
No. mol of 3-nitrobenzaldehyde = Mass of 3-nitrobenzaldehyde
MW
= 0.7489 g
151.12 g/mol
= 0.005 mol
H
H H O
- C = O + CH3- C -
-C=CC-
NO
+ H2O
NO
3-nitrobenzaldehyde
3-nitrochalcone
Percentage yield =
Theoretical yield
= 0.5104 x 100%
1.2663
= 40.31%
T.W. Graham Solomons & Craig B. Fry Organic Chemistry, 9th Edition (2007)
Donald L. Pavia, Gary M. Lampman, George S. Kriz, & Randall G. Enge Introduction of Organic
Laboratory Techniques, 2nd Edition (2005)
http://en.wikipedia.org/wiki/Aldol_condensation
http://www.cis.rit.edu/htbooks/nmr/inside.htm
http://en.wikipedia.org/wiki/Chalcone