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Important Concepts
1. Alcohols are alkanols (IUPAC) – Names
derived from stem prefixed by alkyl and halo
substituents
Alcohols Have Polar and Short O-H Bond –
2.
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Hydroxy group is hydrophilic (hydrogen bonding)
Unusually high boiling points
Appreciable water solubility
Alkyl part is hydrophobic
3. Alcohols Are Amphoteric –
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Deprotonation by bases whose conjugate acids are
weaker than the alcohol
Protonation yields alkyloxonium ions
Acidity: primary > secondary > tertiary alcohol
Electron-withdrawing substituents increase acidity
8
Important Concepts
4. Reverse Polarization – i.e., conversion of the
alkyl group in a haloalkane, Cδ+-Xδ-, into its
nucleophilic analog in an organometallic compound,
Cδ--Mδ+.
5. Aldehyde and Ketone Carbonyl Carbons
are Electrophilic – C=O carbon is subject to attack
by hydride hydrogens or organometallic alkyl groups.
Aqueous workup yields alcohols.
6. Oxidation of Alcohols – Yields aldehydes and
7.
ketones (Chromium IV reagents).
Retrosynthetic Analysis – Identifies efficient
sequence of reactions by identifying strategic bonds.