1. An organic compound (A) has molecular formula (C₅H₁₀O). It does not reduce Tollen's reagent but forms an orange precipitate with 2,4-DNP reagent. (A) does not give yellow prcipate on treatment with NaOH and I_2. Under vigorous conditions of oxidation (A) gives one molecule of a carboxylic acid (B) with molecular formula, C₂H₆O₂ and one molecule of another carboxylic acid (C) with molecular formula , C₂H₄O₂ . Sodium salt of (B) gave a hydrocarbon (D) in Kolbe's Electrolytic reaction. Identify (A), (B), (C) and (D) and write the reactions involved.
   
2. Predictthe products formed( with formation ) in the following cases
   

i) When (A) reacts with PhMgBr and is then hydrolysed

ii) When (A) reacts with hydrazine and is then heated with KOH and ethylene glycol.

It does not reduce tollen’s reagent then compound (A) should be an aldehyde or ketone.

It forms orange precipitate with 2,4-DNP reagent therefore it should be either aldehyde or ketone.

It does not give yellow precipitate on treatment with NaOH and iodine (iodoform reaction). Then it is not an aldehyde and should not be a methyl ketone and hence it is diethylketone (C₅H₁₀O) satisfies molecular formula for(A).

Diethyl ketone on oxidation vigorously gives ethanoic acid (B) C₃H₆O₂  and

acetic acid (C) C₂H₄O_2.

Ethanoic acid  reacts with sodium hydroxide giving sodiumethoxide, on Klobe’s electrolytic reduction gives ethane (D) C₂H_6.

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1. Diethyl ketone reacts with grignard reagent and then under goes hydrolysis to give tertiary alcohol.

2. Diethyl ketone under goes wolff-kishner reduction to give alkanes. Diethyl ketone reacts with hydrazine to form hydrazone and further reaction with base KOH gives pentane.