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Solution: Many compounds with desirable medicinal properties are isolated from natural sources and are thus referred to as natural products. However, a compound’s medicinal properties are often known before the structure of the compound has been determined. Below are examples of compounds where the first proposed structure was incorrect (Angew. Chem. Int. Ed. 2005, 44, 1012–1044). In each case, the corresponding correct structure is also shown. Identify all functional groups in each pair of compounds and then compare the similarities and differences between their molecular structures. 

Problem

Many compounds with desirable medicinal properties are isolated from natural sources and are thus referred to as natural products. However, a compound’s medicinal properties are often known before the structure of the compound has been determined. Below are examples of compounds where the first proposed structure was incorrect (Angew. Chem. Int. Ed. 2005, 44, 1012–1044). In each case, the corresponding correct structure is also shown. Identify all functional groups in each pair of compounds and then compare the similarities and differences between their molecular structures.