Compound A with the molecular formula (C3H8O) on oxidation gives compound B, which does not undergo...

Compound A with the molecular formula (C3H8O) on oxidation gives compound B, which does not undergo Tollen’s test. Give the condensed structural formula for compound A. Give the IUPAC name for compound A. Spell out the full name of the compound. Give the condensed structural formula for compound B.

Solutions

Expert Solution

Molecular formula of starting (A) is C3H8O which fits for saturated alcohol and ether. Ether possibility ruled out as it’s oxidation less possible. The compound with C3H8O m.f. most probably an alcohol.

There are 2 possibilities i.e. 1-Propanol and 2-Propanol will give Propanal and Propan-2-one on oxidation respectively.

If oxidizing agent like Chromic acid used then 1-Propanol will be directly converted into Propanoic acid.

Given that the product of oxidation of (A) is (B) and (B) don not shows Tollen’s test which is characteristic test for aldehyde. Hence (B) is not aldehyde certainly. Carboxylic acid and ketones do not give Tollen’s test.

Now 2 possibilities are there

A is 1-Propanol and oxidized to Propanoic acid (B) using strong oxidizing agent. OR
A is 2-Propanol oxidized to 2-Propanone using mild oxidant like PCC.

Depending on this two structures for A and B proposed.

If A is 1-Propanol then B is Propanoic acid and
If A is Propan-2-ol then B is Propan-2-one

queen_honey_blossom answered 1 year ago

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