Home
Class 12
CHEMISTRY
A compound A(C(2)H(6)O) on oxidation by ...

A compound `A(C_(2)H_(6)O)` on oxidation by PCC give B, which on treatment with aqueous alkali and subsequent heating furnished C. Bon oxidation by `KMnO_(4),` forms a monobasic carboxylic acid with molar mass 60 g `mol^(-1)` Deduce the structures of A, B and C.

Text Solution

Verified by Experts

Monobasic carboxylic acid = RCOOH Given that, molar mass of RCOOH = 60 g `mol^(-1)` i.e.` x+ 12 + 16 + 16 + 1 = 60 = x= 15 `
Thus, `R= - CH_(2)` (molar mass 15) and the acid is CH,COOH. Since, the acid is obtained by the oxidation of aldehyde, so Bis an aldehyde, i.e. CH,CHO and A is `CH _(3) CH _(2)OH.` Thus, the reactions are as follows:
`CH _(3) - underset((A)) ( CH _(2)) - OH overset( PC C ) to CH _(3) - underset((B)) overset(O) overset(||) (C) - H overset(KMnO _(4)) to {:(CH _(3) - overset(O) overset(||) (C) - OH) , (("M, wt. 60 g" mol ^(-1))):}`
`2 CH _(3) - underset((B)) overset( O ) overset(||) (C) - H underset( "Aldol condensation ") overset( OH ^(-)) to CH _(3) - overset( OH) overset(|)(CH) - underset (darr"Heat") (CH _(2)) - overset(O) overset(||) (C) - H `
`CH _(3) - CH underset((C)) (=) CH - overset( O ) overset(||) (C) - H`
Promotional Banner

Similar Questions

Explore conceptually related problems

An aromatic compound A on treatment with aqueous ammonia and heating forms compound B which on heating with Br_(2) and KOH forms a compound C of molecular formula C_(6)H_(7)N . Write the structures and IUPAC names of compounds A, B and C.

An organic compound A (C_(4)H_(10)O ) reacts with HI giving a compound B( C_(4)H_(9)l ), which on reduction gives n-butane. On oxidation 'A' gives a compound C(C_(4)H_(8)O ) and then an acid D(C_(4)H_(8)O_(2)) . Deduce the structures of A, B, C and D and mention their IUPAC names.

An organic compound (P) having molecular formula C_(9)H_(10)O form an orange precipitate (Q) with 2,4-DNP reagent. Compound (P) gives a yellow precipitate (R ) when heated in the presence of iodine and NaOH along with a colourless compound (S). (P) neither reduce Tollen's reagent or Fehling's solution nor it decolourises bromine water. On drastic oxidation of (P) with chromic acid, a carboxylic acid (T) having molecular formula C_(7)H_(6)O_(2) is obtained. Deduce the structures of the compounds (P) to (T).

(i) How will you convert phenol to benzoic acid? (ii) An organic compound A having molecular formula, C_6H_6O gives a characteristic colour with aqueous FeCl_3 solution. A on treatment with CO_2 and NaOH at 400 K under pressure gives B which on acidification gives a compound C. The compound C reacts with acetyl chloride to give D which is a popular pain killer. Deduce the structure of A, B, C and D.