Chapter 13: Getting Drunk on Organic Molecules: The Alcohols

Getting Drunk on Organic Molecules: The Alcohols classification system is essential because it directly determines how alcohols behave in subsequent reactions. Students learn systematic nomenclature using IUPAC conventions, which requires identifying the longest carbon chain containing the hydroxyl group, numbering the chain to assign the lowest position number to the oxygen atom, and properly sequencing any substituents. The chapter then explores multiple synthetic pathways for constructing alcohols. Alkene hydration through oxymercuration-demercuration follows Markovnikov's rule to produce the more substituted alcohol, while hydroboration-oxidation provides the complementary anti-Markovnikov product. Reduction reactions represent another major synthetic approach: sodium borohydride reduces aldehydes and ketones to primary and secondary alcohols respectively, whereas lithium aluminum hydride is a more powerful reducing agent capable of converting esters and carboxylic acids to alcohols. The Grignard reaction, involving nucleophilic attack by an organometallic species on carbonyl electrophiles, enables synthesis of all three alcohol types depending on the starting carbonyl substrate. The chapter also covers alcohol reactivity, including dehydration mechanisms that generate alkenes using phosphorus oxychloride, nucleophilic substitution reactions leading to ether formation through Williamson ether synthesis, and oxidation transformations using selective oxidizing agents like pyridinium chlorochromate or Jones reagent to produce aldehydes, ketones, or carboxylic acids. Together, these reactions demonstrate alcohols as versatile functional group intermediates in synthetic organic chemistry.