Cocaine is a widely abused, addicting drug. Cocaine is usually obtained as its

Chapter 3, Problem 3.42

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Cocaine is a widely abused, addicting drug. Cocaine is usually obtained as its hydrochloride salt (cocaine hydrochloride) but can be converted to crack (the neutral molecule) by treatment with base. Which of the two compounds here has a higher boiling point? Which is more soluble in water? How does the relative solubility explain why crack is usually smoked but cocaine hydrochloride is injected directly into the bloodstream? N COOCH3 CH3 H OC O N COOCH3 CH3 H O H Cl cocaine hydrochloride a salt cocaine (crack) neutral organic molecule + C O

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