Question
Question: In the following reaction: \({C_6}{H_5}MgBr + C{O_2} \to A\xrightarrow{{PC{l_5}}}B\) What is A a...
In the following reaction:
C6H5MgBr+CO2→APCl5B
What is A and B?
A. Acid and acid halide
B. Acid and ester
C. Acid halide and acid anhydride
D. Acid anhydride and acid halide
Solution
In the question, the reactants provided are phenyl magnesium bromide and carbon dioxide. Phenyl magnesium bromide is an example of Grignard reagent. Carbon dioxide is used as dry ice in this reaction. This reaction is mainly used in the formation of compounds having −COOH group.
Complete step by step answer:
We will proceed with the reaction step wise.
Now, as already mentioned the reactants are phenyl magnesium bromide and carbon dioxide (dry ice). Grignard reagents react in the presence of dry ether with CO2 to form the salts of carboxylic acids.
The salts formed of carboxylic acids will give the main carboxylic acid on acidification with the mineral acid. The reaction can be represented as follows:
C6H5MgBr+CO2dryetherC6H5(CO)O−MgBr+H3O+C6H5COOH
So, the product formed is benzoic acid. It means that A is an acid.
Now, A will react further with PCl5 . In this reaction, the hydroxyl group of carboxylic acid will be replaced by a chlorine atom. The reaction can be represented as follows:
C6H5MgBr+CO2dryetherC6H5COOHPCl5C6H5COCl+POCl3+HCl
Here, the product formed is benzoyl chloride which falls into the category of acyl chloride. It means that B is an acid halide.
So, the reaction given in the question is
C6H5MgBr+CO2→C6H5COOHPCl5C6H5COCl
In the last, we can conclude that A and B are acid and acid halide respectively.
So, the correct answer is Option A.
Note: For the conversion of carboxylic acids into acyl chloride; carboxylic acids can be treated with PCl5, PCl3 and SOCl2 (any of these three). The most preferred among these three is SOCl2 as the side products formed will be gaseous and that will be released. Thus, the main product acyl chloride is attained with purification.