Draw all the possible alcohols with the molecular formula C5H12O and identify the ones that can be oxidized with chromium trioxide

The molecular formula C5H12O represents several alcohol isomers. Here are the possible structures:

  • 1-Pentanol (CH3–(CH2)4–OH)
  • 2-Pentanol (CH3–CH–(CH2)2–OH)
  • 3-Pentanol (CH3–CH2–CH–(CH2)–OH)
  • 2-Methyl-1-butanol (CH3–CH–(CH3)–CH2–OH)
  • 3-Methyl-1-butanol (CH3–CH2–CH–(CH3)–OH)
  • 2-Methyl-2-butanol (CH3–C–(CH3)2–OH)

Among these alcohols, an oxidation reaction with chromium trioxide (CrO3) can occur primarily with the following:

  • 1-Pentanol
  • 2-Pentanol
  • 3-Pentanol
  • 2-Methyl-1-butanol

These alcohols can be oxidized to their corresponding aldehydes or ketones, depending on the position of the hydroxyl (-OH) group. However, tertiary alcohols like 2-Methyl-2-butanol do not undergo oxidation with chromium trioxide, as tertiary alcohols lack a hydrogen atom on the carbon bearing the -OH group, which is necessary for the oxidation process.

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