cerine upon treatment with nitric add. nent of fatty tissue 3 HONO CH:ONO: CH ONO ther): et Explosive when mixed with air Oxacyclopropane (axirane,ethylene oxide) FmgtingaentIoreesanlgans H.C sonandeiherod5aeondnna Important Concepts Mcohols-S.2 reactions ange 4、 rgygeaomeanearangetoseconday 13 13 1,2,3-Propanetriol (glycerol, glycerine): Non-toxic Major component of fatty tissue Liberated by the action of alkali on fats to form soaps: Phosphoric esters of glycerols are major cell membrane components. Used in lotions, cosmetics, and medicinal preparations. Forms nitroglycerine upon treatment with nitric acid. Cholesterol: An important steroid alcohol Ethoxyethane (diethyl ether): Formally used as an anesthetic Explosive when mixed with air Oxacyclopropane (oxirane, ethylene oxide) Industrial chemical intermediate Fumigating agent for seeds and grains Oxacyclopropane derivatives control insect metamorphosis and are formed during enzyme-catalyzed oxidations of aromatic hydrocarbons (highly carcinogenic). Alcohol and ether groups are found in natural products such as morphine and tetrahydrocannabinol: Lower MW thiols and sulfides are notorious for their foul smells. The odor of the skunk’s defensive spray are thiols and a sulfide: When highly diluted, thiols and sulfides have a pleasant odor: freshly chopped onion or garlic, black tea, grapefruit. The compound responsible for the taste of grapefruit can be tasted in concentrations in the ppb range: Drugs such as the sulfonamides (sulfa drugs) contain sulfur in their molecular framework: 9 Important Concepts 1. Reactivity of ROH With Alkali Metals – • R = CH3 > primary > secondary > tertiary 2. Reactions with Acid and a Nucleophilic Counterion – • Primary Alcohols – SN2 reactions • Secondary and Tertiary Alcohols – Form carbocations capable of E1 and SN1 reactions, before and after rearrangement 3. Carbocation Rearrangements – • Hydride and alkyl group shifts • Result in interconversion of secondary carbocations or conversion of secondary to tertiary carbocation • Primary alkyloxonium can rearrange to secondary or tertiary carbocations