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Chemistry Question on Aldehydes, Ketones and Carboxylic Acids

A compound AA has a molecular formula C2Cl3OHC_2 Cl_3 OH . It reduces Fehling's solution and on oxidation, gives a monocarboxylic acid BB. AA can be obtained by the action of chlorine on ethyl alcohol. AA

A

chloroform

B

chloral

C

methyl chloride

D

monochloro acetic acid

Answer

chloral

Explanation

Solution

Molecular formula of A=C2Cl3OHA= C _{2} Cl _{3} OH

As (A)(A) reduces Fehling's solution and on oxidation gives a monocarboxylic acid (B)(B). It means (A)(A) must be an aldehyde.

CCl3CHO(A)CCl_3\,\underset{(A)}{CHO}

This is further confirmed by the reaction

C2H5OH+Cl2>[[o]][oxidation]CH3CHO>[Cl2][chorination]CCl3CHOC_2H_5OH+Cl_2 { ->[{[o]}][{\text{oxidation}}] } CH_3CHO\, { ->[{Cl_2}][{\text{chorination}}] }CCl_3CHO

A= Chloral [CCl3CHO][CCl_3 CHO]