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SolutionsAlcohols, Phenols and Ethers

1. Alcohol, phenol or ether?

Classify each compound:

  1. CH3CH2OH
  2. C6H5OH
  3. CH3OCH3
  4. C6H5CH2OH
  5. Tetrahydrofuran
  6. CH3SH
  1. Alcohol (primary).
  2. Phenol: the OH is bonded to a carbon of the aromatic ring.
  3. Ether.
  4. Alcohol (benzylic): the OH is bonded to an sp3 carbon, not to the ring.
  5. Cyclic ether.
  6. Thiol, the sulfur analogue of an alcohol.

2. Uses and toxicity

Why is ethanol used as an antidote in methanol or ethylene glycol poisoning?

Because it competes with them for the same liver enzyme (alcohol dehydrogenase). While ethanol is being metabolized, methanol or ethylene glycol are not transformed into their toxic metabolites (formaldehyde and formic acid, or oxalic acid) and can be eliminated unchanged.

3. Crown ethers

What is special about crown ethers and why did their study deserve the 1987 Nobel Prize?

They are cyclic ethers with several oxygens forming a cavity that can selectively host a metal cation according to its size. They were the first simple examples of molecular recognition and gave rise to Supramolecular Chemistry (Pedersen, Lehn and Cram).

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