Chapter 17: Q.1. (page 641)
Question: Draw all possible resonance structures for the antihistamine diphenhydramine, the active ingredient in Benadryl.
Short Answer
Answer
Resonating structures of diphenhydramine.
Chapter 17: Q.1. (page 641)
Question: Draw all possible resonance structures for the antihistamine diphenhydramine, the active ingredient in Benadryl.
Answer
Resonating structures of diphenhydramine.
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a. How many electrons does C contain?
b. How many electrons are delocalized in the ring?
c. Explain why C is aromatic.
Question: Stanozolol is an anabolic steroid that promotes muscle growth. Although stanozolol has been used by athletes and bodybuilders, many physical and psychological problems result from prolonged use and it is banned in competitive sports.
a. Explain why the nitrogen heterocycle—a pyrazole ring—is aromatic.
b. In what type of orbital is the lone pair on each N atom contained?
c. Draw all reasonable resonance structures for stanozolol.
d. Explain why the of the N-H bond in the pyrazole ring is comparable to the of O-H bond, making it considerably more acidic than amines such as ( = 40).
Question: Januvia, the trade name for sitagliptin, was introduced in 2006 for the treatment of type 2 diabetes. (a) Explain why the five-membered ring in sitagliptin is aromatic. (b) Determine the hybridization of each N atom. (c) In what type of orbital does the lone pair on each N atom reside?
Question: Explain why tetrahydrofuran has a higher boiling point and is much more water soluble than furan, even though both compounds are cyclic ethers containing four carbons.
Question: Explain why A is aromatic but B is not aromatic.
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