A student synthesized Compound 1 (below). To purify the compound, she extracted

Question

A student synthesized Compound 1 (below). To purify the compound, she extracted it into aqueous base and then acidified the solution to protonate the acid so that she could extract it back into ether. When she evaporated the ether, she found that her product had been converted entirely into Compound 2 What is the functional group that forms the ring in Compound 1? In Compound 2? How many carbon atoms are there in Compound 1? In Compound 2? Where did the other carbon atoms go? When did the reaction occur: When the student added the base, or when she added the acid? Propose a mechanism for the conversion of Compound 1 to Compound 2.

Explanation / Answer

a) compound 1 - ether compound 2 - carboxyl b)compound 1 - 7 compound 2 - 5 c) acid

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