Question

Acid catalyzed hydration (H2SO4/water/△) of an unknown compound (A)with a chemical formula C6H12, yielded a racemic mixture of product C6H13OH. Which, if any, of the following compounds is/are possible structures for the initial compound (A)?

A) compound 1 only
B) compounds 2 and 3
C) compound 2 only
D) compounds 1 and 3
E) none of the above

Answer 1

When an unknown compound with a chemical formula C6H12 undergoes acid-catalyzed hydration, a racemic mixture of product C6H13OH is obtained. The only possible structure for this initial compound is compound 2.

Step-by-step explanation:

When an unknown compound (A) with a chemical formula C6H12 undergoes acid-catalyzed hydration, a racemic mixture of product C6H13OH is obtained. Let's analyze which of the compounds provided could be possible structures for compound (A).

Compound 1 and compound 3 both have the molecular formula C6H12. Compound 1 has no chiral carbon, which means it cannot produce a racemic mixture, so it is not a possible structure for compound (A). Compound 3 has a chiral carbon, but when it undergoes acid-catalyzed hydration, it would produce a product with two enantiomers, not a racemic mixture. Therefore, compound 3 is also not a possible structure for compound (A).

Compound 2, on the other hand, has a chiral carbon and can produce a racemic mixture when it undergoes acid-catalyzed hydration. Hence, the only possible structure for the initial compound (A) is compound 2.