ChemistryNEB 2076 (old course)

An organic Compound C3H6O does not give silver mirror with tollen's reagent but gives yellow precipitation with NaOH and I2 . Identify the compound and write the reactions involved.

2

Answer

The given organic compound is with the following properties:

  1. No silver mirror with Tollen’s reagent: Rules out aldehydes (which give a positive test).
  2. Yellow precipitate with and : Confirms the presence of a methyl ketone (iodoform test).

Identification:

The compound is propanone (acetone) ().

Propanone (Acetone)Propanone (Acetone)
Structural formula of acetone (CH₃COCH₃) showing the carbonyl group (C=O) responsible for its reactivity.

Reactions:

  1. Iodoform test (yellow precipitate):
CHI₃ (Iodoform)CHI₃ (Iodoform)
Yellow precipitate of iodoform (CHI₃) formed in the iodoform test, confirming the methyl ketone functional group.
acetoneacetone+3I₂+4NaOHheatiodoformiodoform+CH₃COONa+33NaI+33H₂O
Iodoform test: Acetone reacts with iodine and sodium hydroxide to form a yellow precipitate of iodoform (CHI₃).
  1. No reaction with Tollen’s reagent (since it is a ketone, not an aldehyde):

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