An organic compound (A) having molecular formula C₄H₈O gives orange red precipitate with 2, 4-DNP reagent. It does not reduce Tollen’s reagent but gives yellow precipitate of iodoform on heating with NaOH and I₂. Compound (A) on reduction with NaBH₄ gives compound (B) which undergoes dehydration reaction on heating with conc. H₂SO₄ to form compound (C). Compound (C) on ozonolysis gives two molecules of ethanol.

(a)  Identify (A), (B) and (C).

(b)  Write the structures (A), (B) and (C).

Write the reactions of compound (A) with

(c)   NaOH / I₂ and

(d) NaBH₄.  

OR

An organic compound (A) with molecular formula C₂Cl₃O₂H is obtained when (B) reacts with Red P and Cl₂. The organic compound (B) can be obtained on the reaction of methyl magnesium chloride with dry ice followed by acid hydrolysis.

(a)   Identify A and B

(b)   Write down the reaction for the formation of A from B. What is this reaction called?

(c)   Give any one method by which organic compound B can be prepared from its corresponding acid chloride.

(d)   Which will be the more acidic compound (A) or (B)? Why?

Write down the reaction to prepare methane from the compound (B).