(a) Write a suitable chemical equation to complete each of the following transformations:
(i) Butan-1-ol to butanoic acid
(ii) 4-methylacetophenone to benzene-1, 4-dicarboxylic acid
(b) An organic compound with molecular formula C9H10O forms 2, 4-DNP derivative, reduces Tollen’s reagent and undergoes Cannizzaro’s reaction. On vigorous oxidation, it gives 1, 2-benzenedicarboxylic acid. Identify the compound.
(i) Butanoic acid can be obtained by oxidation of butan-1-ol.
The most common reagent used for oxidation of alcohols is chromium (Vl) reagents including chromic acid (H2CrO4), potassium dichromate (K2Cr2O7) and chromic anhydride (CrO3).
(ii) 4- methylacetophenone can be converted to benzene-1, 4- dicarboxylic acid as follows:
(b) It is given that the compound (with molecular formula C9H10O) forms 2, 4-DNP derivative and reduces Tollen’s reagent. Therefore, the given compound must be an aldehyde.
Again, the compound undergoes Cannizzaro reaction and on oxidation gives 1, 2-benzenedicarboxylic acid. Therefore, the -CHO group is directly attached to a benzene ring and this benzaldehyde is ortho-substituted. Hence, the compound is 2-ethylbenzaldehyde.
2 – ethyl bezaldehyde
The given reactions can be explained by the following equations.
