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 molecule?
(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.

Transcribed Image Text:

H Н C. Н Н H H -c-CH3 -H :N Н Amphetamine