Question

Predict the product of reaction of aniline with bromine in non-polar solvent such as CS2.

Answer 1

A mixture of 2-bromoaniline and 4-bromoaniline is formed.

Answer 2

The reaction of aniline with bromine in non-polar solvent such as $CS_2$ yields one major product and one minor product.

Explanation:

• In non-polar solvents such as $CS_2$, aniline exhibits high resonance due to which it becomes ready to undergo reduction.
• Due to this the effect of $NH_2$ attached in the aniline, in gets reduced and a process called mono-substitution takes place in the "para" and "ortho" positions.

• In the "ortho" position the bromine group gets attached to the second carbon of the aniline ring and leads to the formation of a minor product called 2-Bromoaniline.

• On the other hand in the "para" position, the bromine group gets attached to the fourth carbon of the aniline ring and leads to the formation of major product called 4-Bromoaniline.
• The structure of the major and minor products are given in the attachment.

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