Chapter 11, Problem 26P

Answer the following questions about erlotinib and phomallenic acid C. Erlotinib, sold under the trade name Tarceva, was introduced in 2004 for the treatment of lung cancer. Phomallenic acid C is an inhibitor of bacterial fatty acid synthesis.

a. Which $\text{C}-\text{H}$ bond in erlotinib is most acidic?

b. What orbitals are used to form the shortest $\text{C}-\text{C}$ single bond in erlotinib?

c. Which H atom in phomallenic acid C is most acidic.

d. How many $sp$ hybridized carbons are contained in phomallenic acid C?

e. Rank the labeled bonds in phomallenic acid C in order of increasing bond strength.