Glycerol on heating with anhydrous magnesium sulphate yield an acid smelling distillate of molecular formula of C3H4O which immediately decolouries bromine water and restore the colour to Schiff's reagent. Indicate a possible structure for the compound

Chemistry

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Answer

CH2=CH−CHO\text{CH}_2=\text{CH}-\text{CHO}

Step-by-step solution

4 steps
  1. Determine the degree of unsaturation (DoU) for the compound with molecular formula C3H4O\text{C}_3\text{H}_4\text{O}.

    The formula for DoU is C+1−H2−X2+N2\text{C} + 1 - \frac{\text{H}}{2} - \frac{\text{X}}{2} + \frac{\text{N}}{2}, where C is carbon, H is hydrogen, X is halogen, and N is nitrogen.
    For C3H4O\text{C}_3\text{H}_4\text{O}:

    DoU=3+1−42−02+02=4−2=2\text{DoU} = 3 + 1 - \frac{4}{2} - \frac{0}{2} + \frac{0}{2} = 4 - 2 = 2

    A DoU of 2 indicates the presence of two double bonds, one triple bond, or one ring and one double bond.

  2. Interpret the chemical properties.

    • "Immediately decolorizes bromine water" indicates the presence of a carbon-carbon double bond (C=C\text{C}=\text{C}) or a triple bond (C≡C\text{C}\equiv\text{C}). This accounts for at least one degree of unsaturation.
    • "Restore the colour to Schiff's reagent" indicates the presence of an aldehyde functional group (-CHO\text{-CHO}). An aldehyde group contains a carbon-oxygen double bond (C=O\text{C}=\text{O}), which accounts for one degree of unsaturation.
    • "Acid smelling distillate" refers to the pungent, acrid smell characteristic of small aldehydes.
  3. Combine the functional groups with the molecular formula and DoU.

    Since the compound has an aldehyde group (C=O\text{C}=\text{O}, 1 DoU) and a carbon-carbon double bond (C=C\text{C}=\text{C}, 1 DoU), these two features together account for the total DoU of 2.
    With 3 carbon atoms, we can arrange these groups as follows:
    The aldehyde group is at one end of the carbon chain. The carbon-carbon double bond must be between the other two carbons.

  4. Propose and verify the structure.

    The only possible arrangement for C3H4O\text{C}_3\text{H}_4\text{O} containing both a C=C\text{C}=\text{C} bond and an aldehyde (-CHO\text{-CHO}) group is prop-2-enal, also known as acrolein.
    Its structure is CH2=CH−CHO\text{CH}_2=\text{CH}-\text{CHO}.
    Let's check the formula: 3 carbons, 2+1+1 = 4 hydrogens, 1 oxygen. This matches C3H4O\text{C}_3\text{H}_4\text{O}.
    The reaction of glycerol with a dehydrating agent like anhydrous magnesium sulfate is known to produce acrolein.

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