Question

Kindly Answer this question. ( Question 35 ) ​

Answer 1

Question:

An acid A $(C_{8}H_{7}O_{2}Br)$ on bromination in the presence of $Fe{Br}_{3}$ gives two isomers B and C of the formula $C_{8}H_{6}O_{2}{Br}_{2}$.

Vigorous oxidation of A, B and C gives acids D, E and F respectively. The acid D, $C_{7}H_{5}O_{2}Br$ is the strongest acid among all other isomers whereas E and F each has molecular formula of $C_{7}H_{4}O_{2}{Br}_{2}$. Give structures of A to F with justification.

Answer:

Refer to the attachment !!

Explanation:

• The acid A has a COOH group due to presence of two oxygen atom and a Br atom.
• As on bromination, it gives two isomeric dibromo derivatives, the two groups in the aromatic acid A must be at the ortho positions.
• Tge compound A on bromination gives two isomers B and C, thus the position of the incoming group should be ortho and para with respect to the Br atom present.
• Since, the corresponding oxidised product D of an aromatic acid (A) is the strongest acid as compared to other isomers, i.e. ortho and para.
• Thus the possible structure of A is : Refer to attachment 1 .
• The reactions involved are : Refer to attachment 2.