Chapter 13: Alcohols

Students learn how to predict solubility using hydrogen bonding and the balance between hydrophilic and hydrophobic regions, applying the "five-carbon rule" to assess water miscibility. Klein explains how alcohol acidity relates to the stability of the conjugate base, influenced by resonance (as in phenol) and inductive effects (such as nearby electronegative atoms). Methods of alcohol synthesis are reviewed and expanded through reduction reactions (using LiAlH₄ or NaBH₄) and Grignard additions, which enable carbon–carbon bond formation from aldehydes and ketones. Students learn to control oxidation states and predict when an oxidation or reduction is occurring based on electron distribution. The chapter also explores reactions of alcohols, including elimination (E1 and E2) and substitution (SN1 and SN2), emphasizing that alcohols must first be converted into good leaving groups (via protonation, tosylation, or conversion to alkyl halides). Finally, students are introduced to the Williamson Ether Synthesis, which uses alkoxide ions in SN2 reactions to form ethers. With numerous reaction maps, oxidation state logic, and functional group transformations, this chapter equips students with a versatile toolkit for synthesis and mechanistic prediction involving alcohols.