Question

Draw the organic product(s) of the reaction of p-methylbenzoic acid with CH3MgBr in dry ether, then H3O+ in the window below. If no new products are formed, tell OWL by drawing ethane, CH3CH3.

Answer 1

Methane is produced as a new product.

Step-by-step explanation:

`CH_(3)MgBr` acts as a base toward -COOH group in p-methylbenzoic acid.

Hence an acid-base reaction occurs between p-methylbenzoic acid and
`CH_(3)MgBr` to produce methane and p-methylbenzoate.

`H_(3)O^(+)`addition will convert p-methylbenzoate back to p-methylbenzoic acid.

Hence, methane is produce as a new product.

Reaction sequences are given below.