Chapter 9, Problem 48GQ

The structure of amphetamine, a stimulant, is shown below. (Replacing one H atom on the NH₂, or amino, group with CH₃ gives methamphetamine a particularly dangerous drug commonly known as “speed.”)

(a) What are the hybrid orbitals used by the C atoms of the C₆ ring. by the C atoms of the side chain, and by the N atom?

(b) Give approximate values for the bond angles A, B, and C.

(c) How many σ bonds and π bonds are in the molerule?

(d) Is the molecule polar or nonpolar?

(e) Amphetamine reacts readily with a proton (H⁺) in aqueous solution. Where does this proton attach to the molecule? Explain how the electrostatic potential map predicts this site of protonation.