17.6k views
1 vote
How can 2-phenylethanoic acid can be prepared from toluene?​

User Giraphi
by
8.1k points

1 Answer

2 votes

Answer: C6H5CH3 (toluene) + Br2 + Mg + CO2 + oxidizing agent → C6H5CH2COOH (2-phenylethanoic acid)

Step-by-step explanation:

2-Phenylethanoic acid, also known as phenylacetic acid, can be prepared from toluene through the following steps:

Bromination: Toluene is brominated using Br2 and FeBr3 as a catalyst to form 2-bromotoluene.

Grignard reaction: The 2-bromotoluene is reacted with magnesium (Mg) in dry ether to form phenylmagnesium bromide (C6H5MgBr).

Acidification: The phenylmagnesium bromide is then reacted with carbon dioxide (CO2) to form 2-phenylpropanoic acid (also known as phenylpropionic acid). This reaction is carried out by bubbling CO2 gas through the solution of phenylmagnesium bromide in dry ether.

Oxidation: The 2-phenylpropanoic acid is then oxidized using a strong oxidizing agent, such as potassium permanganate (KMnO4) or chromic acid (H2CrO4), to form 2-phenylethanoic acid.

The overall reaction can be represented as follows:

C6H5CH3 (toluene) + Br2 + Mg + CO2 + oxidizing agent → C6H5CH2COOH (2-phenylethanoic acid)

Note: This is a complex reaction sequence and should only be attempted by experienced chemists in a well-equipped laboratory with appropriate safety measures.

User Haseeb Ahmad
by
8.6k points