Integrated SequencePhysics Chemistry Organic Biology

Web Resources

Wikipedia - Deprotonation of Alcohols
Concise characterization of the acidity of alcohols.

Virtual Textbook of Organic Chemistry - Acidity of Phenols
Phenol is much more acidic than ordinary alcohols.

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Special points of emphasis


The Chemical Bond

Functional Groups in Organic Chemistry


Chemical Thermodynamics and the Equilibrium State


Acids and Bases

Organic Acids and Bases

We have discussed how alkoxide anions are less stable than similarly sized carboxylate anions. Did you know that alkoxide is even less stable than hydroxide? Alcohols are weaker acids than water.

The alkoxide anion is less stable than hydroxide both because of the weakly electron donating nature of aliphatic groups (pushing negative charge onto negative charge increases energy) and the reduced access to the anion by solvating water molecules because of the aliphatic portion of the molecule.

Organic Acids and Bases

Reactions of Alkyl Halides

Usually formed by reduction with alkali metals, the conjugate base of alcohols, alkoxides, are important nucleophiles in organic chemistry.

However, because alkoxide anions are strong bases, substitution is practical only for primary alkyl halides. With secondary and tertiary substrates, elimination predominates.

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