Aldol condensation

You are to prepare anisalacetophenone (AKA 4-methoxychalcone) via an aldol condensation according to the directions on page 323 of your lab text. You will recrystallize the crude product from 95% ethanol. Run the nmr and IR (CCl4) spectra of your product.

answer the following questions:

1) In the aldol condensation you ran:

a) Why doesn't the ketone undergo a self-condensation?

b) Why doesn't the aldehyde undergo the Cannizzaro

reaction?

c) Write equations for both of the above reactions.

2) Are there geometric isomers of the product of this synthesis? Draw them. Is the reaction stereoselective or stereospecific? Which product is actually formed and why.

3) Predict the products of the following:

a) butyraldehyde, dil. NaOH

b) formaldehyde, conc. NaOH

c) acetone, p-tolualdehyde(2 mol), dil NaOH

d) 2,2-dimethylpropanal, formaldehyde, conc. NaOH

e) benzaldehyde, methyl acetate, sodium methoxide

4) Why does the intermediate in the synthesis undergo spontaneous dehydration?

5) Show the stereochemistry of the hydroxylation with potassium permanganate of trans- anisalacetophenone using Fischer projections.

Answer question 4 on page 325 of your lab text.