Solution Found!
Draw the structure of the product that is obtained when
Chapter 22, Problem 22.84(choose chapter or problem)
Draw the structure of the product that is obtained when acetophenone is treated with each of following reagents: (a) Sodium hydroxide and excess iodine followed by H3O+ (b) Bromine in acetic acid (c) Aqueous sodium hydroxide at elevated temperature
Questions & Answers
QUESTION:
Draw the structure of the product that is obtained when acetophenone is treated with each of following reagents: (a) Sodium hydroxide and excess iodine followed by H3O+ (b) Bromine in acetic acid (c) Aqueous sodium hydroxide at elevated temperature
ANSWER:Step 1 of 3
(a) The first set of reagents is sodium hydroxide and excess iodine followed by aqueous acid.
This is a variant of the haloform reaction. The sodium hydroxide deprotonates acetophenone at the alpha position and the resulting enolate is quenched with iodine. This happens three times until all the alpha protons have been replaced by iodines. At that point, hydroxide anion can attack the electrophilic carbonyl carbon, forming a tetrahedral intermediate. Reformation of the carbonyl kicks off a triiodemthyl anion as a leaving group.
The reaction as follows:
Therefore, the product of the reaction is benzoic acid.
