Instead of the usual dark purple 2,3,4,5-tetraphenylcyclopentadienone product, a

Question

Instead of the usual dark purple 2,3,4,5-tetraphenylcyclopentadienone product, a (fictional) Chem 246 student isolated a different crystalline solid from the aldol reaction of Chapter 14. After a significant amount of spectroscopic analysis, the student determined the molecular structure of this substance and named it compound X. After referring to their own laboratory notebook narrative, the student made a shocking discovery: One important detail of the procedure was completely forgotten! Consider the structure of compound X and determine what part of the procedure was not performed. Propose a mechanism for the synthesis of this product. The student isolated 1.38 g of pure compound X from the reaction. If the reaction was carried out on the same scale as your Chapter 14 experiment, what is the % yield of this product?

Explanation / Answer

its an aldol reaction:

the initial compound is the centre compound without the two branches, i.e, two benzene rings joined by 3 carbon linear chain and a ketone at the centre. By taking 3 of these molecules, and reacting with a mild base, we can form aldol reaction to form the given product.

first the base takes proton from the carbon adjacent to benzene, and a negative charge develops there. This negative charge attacks the ketone of the 2nd starting compound, which undergoes dehydration to form one of the branches. This step repeats with the another carbon of the starting compund, thus both branches attaches.

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