Asked in NUMS 2018 2018Moderate

The compound 'leaf alcohol' is partly responsible for the smell of new - mown grass CH3CH2CH=CHCH2CH2OH Leaf alcohol Which two compounds will be formed when 'leaf alcohol' is oxidized using hot, concentrated manganate (VII) ions?

Correct answer: C. CH3CH2CO2H and HO2CCH2CO2H

  • A. CH3CO2H and HOCH2CH2CH2CO2H
  • B. CH3CO2H and HO2CCH2CH2CO2H
  • C. CH3CH2CO2H and HO2CCH2CO2H
  • D. CH3CH2CO2H and HOCH2CH2CO2H

Explanation

The answer is C as when the double bond breaks, based on the structure of both the carbons involved in the double bond, each having a hydrogen attached alongside an organic chain, aldehydes would be formed. Both the aldehydes would be oxidized to give carboxylic acid. CH3CH2COOH is formed plus COOHCH2CH2OH with the latter being a primary alcohol. It would be further oxidized to give a dicarboxylic acid which is HOOCCH2COOH, thus the answer is C.

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About Alcohols

Alcohols contain a hydroxyl group attached to a saturated carbon atom and are classified as primary, secondary or tertiary. Their nomenclature, hydrogen bonding, acidity, oxidation, dehydration, reaction with sodium and conversion to haloalkanes are covered, along with the distinction between alcohols and phenols, where the hydroxyl group is attached directly to an aromatic ring.

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