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6) Scenario: You are responsible for preparing 2-butoxynapthalene, a flavouring agent that has a strong
raspberry taste. You look up the procedure for the preparation of your target compound and find the
Sodium hydroxide (0.560 g) is added to a solution of 2-naphthol (0.995 g) in ethanol (14 ml) and
the solution is heated to reflux. Once both the sodium hydroxide and the 2-naphthol go into
solution, the 1-iodobutane (1.00 mL) is added slowly. After 15 minutes, the reaction mixture is
poured over ice water and the resulting precipitate is collected by suction filtration. The crude
melting point is determined, and percentage yield is calculated.
a) What is the full reaction mechanism for the preparation of 2-butoxynapthalene as described
above? Include all reactions, structures, arrows and relevant charges where necessary. (3
b) Explain why the target product would not be readily produced from a reaction between 1-
butanol and 2-iodonaphthalene, in NaOH/EtOH? (2 Marks)

Top Answer

a. The reaction mechanism is shown below. b. The reaction of 1-butanol would not work because you would generate a... View the full answer


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