Select the route that would most likely produce the desired results from the given starting material. I. (1) H₂SO₄ and heat; (2) HBr II. (1) KOH in ethanol; (2) HBr
III) (1) H₂SO₄ and heat; (2) HBr + peroxides
IV) (1) potassium tert-butoxide in tert-butanol; (2) HBr + peroxides

Question

Select the route that would most likely produce the desired results from the given starting material.

I. (1) H₂SO₄ and heat; (2) HBr II. (1) KOH in ethanol; (2) HBr
III) (1) H₂SO₄ and heat; (2) HBr + peroxides
IV) (1) potassium tert-butoxide in tert-butanol; (2) HBr + peroxides

Quizplus · Accepted Answer

The desired reaction is a substitution of a bromine atom for a hydrogen atom on the alkane. This is most likely to occur through a radical mechanism, in which a bromine radical attacks the alkane. Option IV involves the formation of a tert-butoxide ion, which can abstract a hydrogen atom from the alkane to form a radical. This radical can then react with HBr to form the desired product. Furthermore, peroxides are used in the second step of this route, which helps initiate the radical mechanism necessary. Therefore, option IV is the best choice for producing the desired product.

Select the Route That Would Most Likely Produce the Desired