Acetylation Procedure Lab 1.pdf

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Chemistry 216 Synthesis of an Analgesic by Acetylation of Aniline Introduction: Acetanilide is an analgesic that was formally known as Antifebrin 1 and is structurally similar to acetaminophen (or Tylenol). However, unlike acetaminophen, acetanilide is toxic. Acetanilide is prepared from aniline using an acetylation reaction. Acetylation is often used to place an acetyl protecting group on primary or secondary amines to reduce their reactivity toward oxidizing agents or electrophiles. 1. Cahn, A; Hepp, P. (1886), “Das Antifebrin, ein neues Fiebermittel”, Centralbl. Klin. Med. 1886 , 7 , 561M65 Objective: In part 1 you will convert aniline to acetanilide using an acetylation reaction described below. In part 2 you will be given an unknown aromatic amine from table 1 below. The amine will be converted into its acetamide analog also using the acetylation procedure described below. Your objective is to compare the two reactions and determine the identity of the unknown amine/acetamide product. Procedure: Reagents: Aniline HCl (concentrated HCl is 37% w/w) Acetic anhydride Sodium acetate Part 1: Dissolve 500 mg of aniline in 14 mL of water. Note that aniline is immiscible in water and two
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