Alcohol Personality Adjustment

by James

Yes, it’s possible to adjust the personality of an alcohol (rather than have it do that to you!). Two ways: by using acid or base.

  • Add acid to an alcohol and you make its conjugate acid (called an “oxonium ion”). This will convert the hydroxyl group to OH2(+), a great leaving group. A common fate of alcohols in acid is that they lose water, either to make a carbocation or in an SN2 reaction.
  • When you add base to an alcohol you make its conjugate base (called an “alkoxide”). This makes the oxygen a better nucleophile (more negative). A common fate of alcohols in base is that they then attack electrophiles (like alkyl halides) to give substitution products such as ethers (among other reactions).

Two examples:

Bottom line: acid makes alcohols into better electrophiles. Base makes alcohols into better nucleophiles.

Thanks for reading!
James