In Chapter 13, we discuss the ring-opening reactions of epoxides, such as the one shown here.

(a) Based on the bonds formed and the bonds broken, calculate ∆H°.

The halogenation of an alkane when there is an alkene present in the molecule does not proceed with the regioselectivity you might expect. Using principles similar to those developed in this chapter, rationalize the formation of A as the only product. We study this reaction further in Chapter 8.

In light of your answers to parts (b) and (c), where both were shown to be quite favorable, imagine a scenario where either reaction is possible. Of the two, which would you expect to be faster? Which would you expect to be more favored? Explain each in the context of the important thermodynamic and/or kinetic parameters.

When a student attempted a bromination to produce compound A, they generated compound B instead. Rationalize the formation of B using the arrow-pushing formalism.

Parts (a)–(d) of this assessment assist in the development of what will become a common theme in organic reactions and should be worked in order. [Think carefully about how each question relates to the others.]

(c) Without worrying about the mechanism of the reaction, estimate an equilibrium constant for the following carbonyl addition reaction based on the relative stability of the Lewis bases.

In Chapter 13, we discuss the ring-opening reactions of epoxides, such as the one shown here.

(b) Predict the sign of ∆S°.

Calculate K_eq for the following acid–base reaction.