Each of these drugs contains one or more building blocks

Chapter 11, Problem 11.4

(choose chapter or problem)

Each of these drugs contains one or more building blocks derived from either ethylene oxide or epichlorohydrin. Cl N N H Moclobemide (an antidepressant) O O OH (a) NH2 N H Atenolol (an antihypertensive) O O (b) O O Me Me OMe Diphenhydramine (Benadryl, an antihistamine) Spasmolytol (an antispasmodic) N Et Et Br N Br (c) (d) O N N Me N N OH Clozapine (an antischizophrenic) Cetirizine (Zyrtec, an antihistamine) (racemic) O N N H Cl (e) (f) Cl Identify the part of each molecule that can be derived from one or the other of these building blocks and propose structural formulas for the nucleophile(s) that can be used along with either ethylene oxide or epichlorohydrin to synthesize each molecule. We will learn about the actual syntheses of each molecule in later chapters.