Question #8862d

1 Answer
Jan 4, 2017

I predict that the product will be 2,4,6-tribromophenol.

Explanation:

The structure of sodium salicylate is

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The phenol group is so activating that the ring will react at all possible ortho and para positions.

The initial product is probably sodium 3,5-dibromo-2-hydroxybenzoate.

www.chemsrc.com

The reaction may stop at this stage but I think that even at 0 °C you also get substitution and decarboxylation of the #"COOH"# group.

The arenium ion formed by attack of #"Br"_2# is easily stabilized by the loss of #"CO"_2# from the carboxylate ion.

Decarboxylation

The product will be 2,4,6-tribromophenol.