An organic compound $(A)$ with molecular formula $C_8H_8O$ forms an orange-red precipitate with $2,4-DNP$ reagent and gives a yellow precipitate on heating with iodine in the presence of sodium hydroxide. It neither reduces Tollens' or Fehlings' reagent,nor does it decolourise bromine water or Baeyer's reagent. On drastic oxidation with chromic acid,it gives a carboxylic acid $(B)$ having molecular formula $C_7H_6O_2$. Identify the compounds $(A)$ and $(B)$ and explain the reactions involved.

Vedclass pdf generator app on play store
Vedclass iOS app on app store
(A) forms a $2,4-DNP$ derivative,which indicates it is an aldehyde or a ketone. Since it does not reduce Tollens' or Fehling's reagent,$(A)$ must be a ketone.
$(A)$ responds to the iodoform test,which confirms it is a methyl ketone.
The molecular formula of $(A)$ indicates a high degree of unsaturation,yet it does not decolourise bromine water or Baeyer's reagent,suggesting the unsaturation is due to an aromatic ring.
Compound $(B)$,being an oxidation product of a ketone,is a carboxylic acid. The molecular formula of $(B)$ corresponds to benzoic acid $(C_6H_5COOH)$.
Therefore,$(A)$ is phenyl methyl ketone (acetophenone,$C_6H_5COCH_3$).
The reactions are as follows:
$1$. Formation of $2,4-DNP$ derivative: $C_6H_5COCH_3 + H_2NNHC_6H_3(NO_2)_2 \rightarrow C_6H_5C(CH_3)=NNHC_6H_3(NO_2)_2 + H_2O$
$2$. Iodoform test: $C_6H_5COCH_3 + 3I_2 + 4NaOH \rightarrow C_6H_5COONa + CHI_3 + 3NaI + 3H_2O$
$3$. Oxidation: $C_6H_5COCH_3 \xrightarrow{H_2CrO_4} C_6H_5COOH$

Explore More

Similar Questions

The best reagent to carry out the following conversion is:
$3$-hydroxyethylcyclopentane-$1$-carbaldehyde $\rightarrow$ $1$-ethyl-$3$-methylcyclopentane (with a hydroxy group on the ethyl side chain).
(Note: The image shows the reduction of an aldehyde group $-CHO$ to a methyl group $-CH_3$ while keeping the secondary alcohol $-CH(OH)CH_3$ intact.)

Difficult
View Solution

Which of the following statements regarding the chemical properties of acetophenone is incorrect?
$I.$ It is reduced to methyl phenyl carbinol by sodium and ethanol.
$II.$ It is oxidized to benzoic acid with acidic $KMnO_4$.
$III.$ It does not undergo electrophilic substitution reactions (like nitration at the $m$-position).
$IV.$ It does not give the iodoform test with iodine and alkali.

Rank the following compounds in order of increasing value of the equilibrium constant for hydration,$K_{hyd}$. (smallest value first).
$1$: Cyclobutanone
$2$: Cyclopropanone
$3$: Di-tert-butyl ketone

The enol form of acetone,after treatment with $D_2O$,gives:

Iodoform test is not given by

Vedclass Products

For Students

Vedclass Test Series

Mock tests in real JEE/NEET style with performance analysis. 5-day free trial.

Start Free Trial
For Teachers

Exam Paper Generator

Generate Set A/B/C/D exam papers from 7.5L+ questions in 2 minutes. 3 chapters free.

Try Free
For Institutes

Online Exam Module

Live online exams with unlimited students, 360° analytics & white-label branding.

See Demo