IIT JEE , AIEEE Forum - Chemistry , Organic Chemistry

linkin_park

An organic compound ' A ' with molecular formula C8 H8 O gives +ve DNP and

iodoform tests. It does not reduce Tollens or fehlings reagent and does not

decolourize bromine water also .On oxidation with chromic acid (H2 Cr O4 ) , it

gives carboxylic acid (B) with molecular formula C7 H8 O2 .Deduce the structures of

A and B .

harsha_27

have u typed the molecular formula of B right?

linkin_park

no I typed th molecular formula of (A) wrong , Question is correct now (edited ) .

harsha_27

is the molecular formula of B right ? i think it must be C7H6O2
and do u want explanation also?or structures are sufficient?....

spideyunlimited

i agree with ur A part answer too. cos it gives positive iodoform so CH3- C=0 linkage has to be present.
B ka i have a doubt too.

linkin_park

yeahhhhh dudes you are right . B is C7 H6 O2 ...sry .

madhusudan.chavan

A gives +ve iodoform test indicates it is methyl ketone as it also gives +ve DNP test. It does not reduce Tollen's reagent indicates absence of aldehydic group. It does not decolourise bromine water suggests compound is not unsaturated. From these facts it ppears that compound (A) is acetophenone C6H5COCH3. Which on oxidation would give benzoic acid C6H5COOH. Please correct the molecular formula of compound (B).

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