The Claisen-Schmidt reaction involves the synthesis of an α,β-unsaturated ketone by the condensation — Organic Chemistry Chemistry Question

The Claisen^-Schmidt reaction involves the synthesis of an α,β-unsaturated ketone by the condensation of an aromatic aldehyde with a ketone. The aromatic aldehyde possesses no hydrogens α-to the carbonyl group, it cannot therefore undergo self condensation but reacts rapidly with the ketone present.

The initial aldol adduct cannot be isolated as it dehydrates readily under the reaction conditions to give an α,β-unsaturated ketone. This unsaturated ketone also possesses activated hydrogens α-to a carbonyl group and may condense with another molecule of the aldehyde.

[VISUAL]

In this experiment you will carry out the base catalysed aldol condensation of p-tolualdehyde with acetone. The product will be purified by recrystallisation and its structure determined using the spectra provided.

Experimental
Substances
* p-tolualdehyde, solid
* acetone, liquid
* sodium hydroxide, 10% aqeous solution
* diethyl ether, liquid
* petroleum ether (*), liquid
_______
(*) This compound will not be used at the Olympiad

Procedure
Dissolve p-tolualdehyde (2.5 cm₃) and acetone (1 cm₃) in ethanol (25 cm₃) contained in a stoppered flask. Add bench sodium hydroxide solution (5 cm₃ of aqueous 10%) and water (20 cm₃). Stopper the flask and shake it for 10 minutes, releasing the pressure from time to time. Allow the reaction mixture to stand for 5 -10 minutes with occasional shaking and then cool in an ice bath. Collect the product by suction filtration, wash it well on the filter with cold water and recrystallise from ethanol.
Record the yield of your product. Run a thin layer chromatogram on a silica plate using ether/petroleum ether 2 : 8 as the eluent and record the Rf value of the product.
Measure and record the m.p. of X.