What is the synthesis of Phenacetin?

Williamson ether synthesis
Phenacetin may be synthesized as an example of the Williamson ether synthesis: ethyl iodide, paracetamol, and anhydrous potassium carbonate are heated in 2-butanone to give the crude product, which is recrystallized from water.

What is the mechanism being used in the Williamson ether synthesis?

Mechanism. The Williamson ether reaction follows an SN2 bimolecular nucleophilic substitution mechanism. In an SN2 reaction mechanism there is a backside attack of an electrophile by a nucleophile and it occurs in a concerted mechanism (happens all at once).

What is the nucleophile in the synthesis of Phenacetin?

Step 2: a conjugate base of p-acetamidophenol (p-acetaminophenozide ion) functions as a nucleophile in its reaction with bromoethane (CH3CH3-Br) to give Phenacetin.

How do you prepare Phenacetin?

Prepare a weakly basic solution by dissolving 0.24 g (2.92 mmol) of sodium acetate (MW 82) in 0.80 mL of water in a 10-mL flask. Set this solution aside for later use. Warm the p-phenetidine hydrochloride solution on a hot plate. Add 0.20 mL (0.22 g, 2.20 mmol) of acetic anhydride (MW 102) while swirling the solution.

What is the theoretical yield of the Williamson ether synthesis product?

1.79 g.
The theoretical yield for the Williamson ether synthesis to produce phenacetin with the given starting reactant amounts is 1.79 g.

What is the major product of Williamson synthesis?

ethers
17.5 The Williamson Ether Synthesis. The Williamson ether synthesis is the most widely used method to produce ethers. It occurs by an SN2 reaction in which a metal alkoxide displaces a halide ion from an alkyl halide. The alkoxide ion is prepared by the reaction of an alcohol with a strong base such as sodium hydride.

Can we get acetaminophen from phenacetin?

(2) Phenacetin can be O-deethylated to acetaminophen, and acetaminophen can be converted directly to a reactive metabolite which may be also N-acetyl-p-benzoquinone imine.

What is the theoretical yield of phenacetin?

Which of the following ethers Cannot be formed from Williamson synthesis?

Williamson’s synthesis required that the alkyl halide should be 1∘ and alkoxide ion may be 1∘,2∘ or 3∘ . Thus, two ethers which cannot be prepared by Williamson’s synthesis are : (C6H5)2O,(CH3)3COC(CH3)3.

What is the general method for Williamson ether synthesis?

What is Williamson Ether Synthesis? The general method for the synthesis of ether is Williamson ether synthesis, involves nucleophilic displacement of a halide ion or other good leaving group by an alkoxide ion. The name of the reaction was coined after Alexander William Williamson developed it in 1850.

How is phenacetin synthesised from acetaminophen?

acetaminophenphenacetin The synthesis of phenacetin from acetaminophen will be accomplished via the Williamson-ether synthesis. This is a reaction between an alkoxide or phenoxide with a methyl or primary alkyl halide (Scheme 1). Scheme 1 depicts an ethoxide reacting with methyl iodide to yield the compound ethyl methyl ether.

How are alcohols used in the Williamson reaction?

Two choices of reactants are available which is finally agreed upon depending on the reactivity and availability. Two alcohols are also used to produce ethers by Williamson reaction. The two are reacted together after one of them is transformed a leaving group (tosylate).

When was phenacetin first used as a medicine?

Acetaminophen was first synthesized in 1877, and first used in humans in 1887. It is the most widely used, non-anti-inflammatory medication for mild to moderate pain relief and fever reduction. Phenacetin is an analog of acetaminophen and was utilized for nearly 100 years until the FDA banned its use (1983) and all products it was contained in.