Chapter 14, Problem 30E

Hot and spicy foods contain molecules that stimulate pain-detecting nerve endings. Two such molecules are piperine and capsaicin:

Piperine is the active compound in white and black pepper, and capsaicin is the active compound in chili peppers.The ring structures in piperine and capsaicin are shorthand notation. Each point where lines meet represents acarbon atom.

1. Complete the Lewis structures for piperine and capsaicin, showing all lone pairs of electrons.
2. How many carbon atoms are $\text{sp}$ , ${\text{sp}}^2$ , and ${\text{sp}}^3$ hybridized in each molecule?
3. Which hybrid orbitals are used by the nitrogen atomsin each molecule?
4. Give approximate values for the bond angles marked a through l in the above structures.