Stanozolol is an anabolic steroid that promotes muscle growth. Although stanozolol has been used by athletes and body builders, 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 pKa of the N – H bond in the pyrazole ring is comparable to the pKa of the O–H bond, making it considerably more acidic than amines such as CH3NH2 (pKa = 40).

Stanozolol is an anabolic steroid that promotes muscle growth. Although stanozolol has been used by athletes and body builders, 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 pKa of the N – H bond in the pyrazole ring is comparable to the pKa of the O–H bond, making it considerably more acidic than amines such as CH3NH2 (pKa = 40).

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter15: Benzene And Aromaticity

Section15.SE: Something Extra

Problem 37AP

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Stanozolol is an anabolic steroid that promotes muscle growth. Although stanozolol has been used by athletes and body builders, 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 pKa of the N—H bond in the pyrazole ring is comparable to the pKa of the O—H bond, making it considerably more acidic than amines such as CH3NH2 (pKa = 40).
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