Chapter 23, Problem 36P

Caftaric acid is found in grapes, wine, and raisins. Rank the labeledprotons in caftaric acid in order of increasing acidity.

Rank the compounds in each group in order of increasing acidity.

Rank the compounds in each group in order of increasing basicity.

Decide which N atom in each molecule is most basic, and draw the product formed when each compound is treated with CH3CO2H. Zolpidem (trade name Ambien) is used to treat insomnia, whereasaripiprazole (trade name Abilify) is used to treat depression,schizophrenia, and bipolar disorders.

Answer the following questions about erlotinib and terbinafine. Erlotinib,sold under the trade name Tarceva, was introduced in 2004 for thetreatment of lung cancer. Terbinafine is an antifungal medication used totreat ringworm and fungal nail infections. Which C–H bond in erlotinib is most acidic? What orbitals are used to form the shortest C–C single bond inerlotinib?

Arrange the compounds in order of increasing acidity.

Which of the following compounds is the LEAST acidic? Select one: -СООН -CH2OH -CH2OH OH

Rank the following compounds in order of increasing basicity and explain the order you chose.

Bupivacaine (trade name Marcaine) is a quick-acting anesthetic oftenused during labor and delivery. Which nitrogen atom in bupivacaine ismore basic? Explain your reasoning.