Question

A C₆H₁₂ compound reacts with ozone to yield a single C₃H₆O product. Gas phase free radical bromination of the hydrocarbon gives a single C₆H₁₁Br product. A likely identification of this compound is ..

A) cyclohexane
B) cyclohexene
C) 3-hexene
D) 2,3-dimethyl-2-butene

Answer 1

The hydrocarbon C6H12 is likely 2,3-dimethyl-2-butene, a symmetrical compound that gives a single product after reaction with ozone and bromine due to its double bond and identical tertiary hydrogen atoms.

Step-by-step explanation:

The compound C6H12 reacts with ozone to yield a single C3H6O product, suggesting that the original compound is symmetrical and likely has a double bond in the middle, as cleavage by ozone normally occurs at the double bond. The fact that free radical bromination of the hydrocarbon gives a single C6H11Br product suggests that there is only one kind of hydrogen that can be abstracted to form a stable radical.

These pieces of information together imply that the hydrocarbon is probably 2,3-dimethyl-2-butene. This substance has a symmetrical structure that would explain the single product formed during ozonolysis. Similarly, it has identical tertiary hydrogen atoms that would explain the single product from bromination. Halogenation reactions like those with bromine (Br2) typically occur at sites that yield the most stable radicals.