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Question

An organic compound (A) with molecular formula C8H8O forms an orange-red precipitate with 2,4 DNP and gives a yellow precipitate of compound (B) on treatment with iodine and sodium hydroxide solution. Compound (A) does not give Tollen's or Fehling test but on drastic oxidation with potassium permanganate, it gives (C) which on reaction with thionyl chloride gives a compound (D) having formula C7H5OCl. (D) on reaction with compound (E) having general formula R2Cd gives back (A)/ Identify (A), (B), (C), (D) and (E). Also, give chemical equations for the reaction involved.

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Solution

Compound A is acetophenone.

It on reaction with I2+NaOH undergoes haloform reaction to form yellow coloured iodoform as a product.

When compound A reacts with KMnO4 it undergoes oxidation to form benzoic acid (C).

When benzoic acid reacts with SoCl2 it forms benzoyl chloride (D) as a product.

When Benzoyl chloride reacts with (R2Cd) it gives corresponding ketone (acetophenone) (A) as a product.

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