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In Section 21-16, we saw that Sevin® insecticide is made
Chapter 15, Problem 60SP(choose chapter or problem)
Problem 60SP
In Section 21-16, we saw that Sevin® insecticide is made by the reaction of 1-naphthol with methyl isocyanate. A Union Carbide plant in Bhopal, India, once used this process to make Sevin® for use as an agricultural insecticide. On December 3, 1984, either by accident or by sabotage, a valve was opened that admitted water to a large tank of methyl isocyanate. The pressure and temperature within the tank rose dramatically, and pressure-relief valves opened to keep the tank from bursting. A large quantity of methyl isocyanate rushed out through the pressure-relief valves, and the vapors flowed with the breeze into populated areas, killing about 2500 people and injuring many more.
(a) Write an equation for the reaction that took place in the tank. Explain why the pressure and temperature rose dramatically.
(b) Propose a mechanism for the reaction you wrote in part (a).
(c) Propose an alternative synthesis of Sevin®. Unfortunately, the most common alternative synthesis uses phosgene, a gas that is even more toxic than methyl isocyanate.
Questions & Answers
QUESTION:
Problem 60SP
In Section 21-16, we saw that Sevin® insecticide is made by the reaction of 1-naphthol with methyl isocyanate. A Union Carbide plant in Bhopal, India, once used this process to make Sevin® for use as an agricultural insecticide. On December 3, 1984, either by accident or by sabotage, a valve was opened that admitted water to a large tank of methyl isocyanate. The pressure and temperature within the tank rose dramatically, and pressure-relief valves opened to keep the tank from bursting. A large quantity of methyl isocyanate rushed out through the pressure-relief valves, and the vapors flowed with the breeze into populated areas, killing about 2500 people and injuring many more.
(a) Write an equation for the reaction that took place in the tank. Explain why the pressure and temperature rose dramatically.
(b) Propose a mechanism for the reaction you wrote in part (a).
(c) Propose an alternative synthesis of Sevin®. Unfortunately, the most common alternative synthesis uses phosgene, a gas that is even more toxic than methyl isocyanate.
ANSWER:
Solution 60SP
Step 1
