Question

Difficulty: EasyAlkanols: Classification, Reactions, Industrial Preparation, and Fermentation

Match each class of alkanol listed on the left with its characteristic oxidation behavior on the right when reacted with acidified potassium heptaoxodichromate(VI) solution.

  • Primary alkanolOxidizes first to an alkanal and subsequently to an alkanoic acid
  • Secondary alkanolOxidizes to form an alkanone (ketone)
  • Tertiary alkanolResists oxidation under mild laboratory conditions

Answer

Primary alkanols pair with oxidation to an alkanal and then an alkanoic acid; secondary alkanols pair with oxidation to an alkanone; tertiary alkanols pair with resistance to oxidation under mild conditions.
Primary alkanols possess two alpha-hydrogens and oxidize in two steps to form alkanals and then alkanoic acids. Secondary alkanols possess one alpha-hydrogen and oxidize to form alkanones. Tertiary alkanols lack alpha-hydrogens entirely, rendering them resistant to oxidation under mild conditions.

Step-by-Step Solution

1
Examine the structural environment of primary alkanols (RCH2OHR-CH_2OH)
Primary alkanols have two α\alpha-hydrogen atoms attached to the carbon holding the OH-OH group, permitting two sequential oxidation steps.
Oxidation requires the removal of hydrogen from the hydroxyl-bearing carbon atom.
2
Examine the structural environment of secondary alkanols (R2CHOHR_2CHOH)
Secondary alkanols have only one α\alpha-hydrogen atom, yielding an alkanone (R2C=OR_2C=O).
Alkanones resist further oxidation under mild conditions because no additional α\alpha-hydrogens are available.
3
Examine the structural environment of tertiary alkanols (R3COHR_3COH)
Tertiary alkanols possess zero α\alpha-hydrogen atoms on the hydroxyl-bearing carbon atom.
Without an α\alpha-hydrogen, oxidation cannot proceed without breaking carbon-carbon bonds.

Key Concept

Classification and oxidation products of alkanols
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