SME
Organic Chemistry I
Alcohols, ethers and epoxides
Use this for “What does 1-propanol give with PCC in CH₂Cl₂, and with Na₂Cr₂O₇ in aqueous H₂SO₄?”
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What does oxidizing each alcohol give?
Tap a card, then tap its group.
Count the H on the lit carbon, then ask whether the reagent works in water or without it.
Assumptions
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An alcohol’s class counts the carbons bonded to the carbon holding the –OH: one is primary (1°), two secondary (2°), three tertiary (3°).
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Oxidation takes an H from that carbon and the H from the O to make a C=O, so that carbon needs at least one H.
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PCC in CH₂Cl₂ and Dess–Martin periodinane work without water, so a 1° alcohol stops at the aldehyde.
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Chromic acid (H₂CrO₄, made from Na₂Cr₂O₇ or CrO₃ with H₂SO₄ in water) and KMnO₄ work in water, so the aldehyde is oxidized on to the acid.
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