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13: Structure and Synthesis of Alcohols

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  • Learning Objectives

    After reading this chapter and completing ALL the exercises, a student can be able to

    • distinguish between alcohols, phenols, enols, and carboxylic acids - refer to section 13.1
    • classify alcohols as primary, secondary, or tertiary - refer to section 13.2
    • predict relative physical properties of alcohols, such as relative boiling points and solubility in a specified solvent - refer to section 13.3
    • determine the structure of alcohols and phenols from spectroscopic data - refer to section 13.4
    • predict the relative acidity of alcohols - refer to section 13.5
    • use resonance to explain why phenols are more acidic than alcohols - refer to section 13.5
    • specify the base needed to ionize an alcohol or phenol - refer to section 13.5
    • predict the products and specify the reagents for alcohol and diol synthesis from alkyl halides, alkenes, and alkynes from the previous chapters - refer to section 13.6
    • predict the products and specify the reagents to synthesize alcohols from the reduction of carbonyls - refer to section 13.7
    • predict the products and specify the reagents to prepare Grignard and organolithium reagents - refer to section 13.8
    • predict the products and specify the reagents for alcohol synthesis from organometallic reagents with aldehydes, ketones, esters, acyl halides, & epoxides - section 13.9
    • distinguish between the structure and reactivity of thiols and sulfides - refer to section 13.10
    • explain the commercial synthesis of alcohols - refer to section 13.11

    Please note: IUPAC nomenclature and important common names of alcohols were explained in Chapter 3.

    • 13.1: Introduction to Structure and Synthesis of Alcohols
      Alcohols, phenols, enols, and carboxylic acids all contain hydroxyl groups.  It is essential to distinguish between the three functional groups.  Because of the structural similarities between alcohols and phenols, their similarities and differences are emphasized.
    • 13.2: Classification of Alcohols
      Alcohols are classified by the bonding pattern of the carbon bonded to the hydroxyl group.  Alcohol classification is helpful in discerning patterns of reactivity.
    • 13.3: Physical Properties of Alcohols
      Alcohols are the first functional group we are studying in detail that is capable of H-bonding.  The effects of increased polarity and stronger intermolecular forces on the physical properties of alcohols relative to alkanes are discussed.
    • 13.4: Spectroscopy of Alcohols
      The hydroxyl group plays an important role in the spectroscopy of alcohols and phenols.
    • 13.5: Acidity of Alcohols and Phenols
      Phenols are weakly acidic (pKa = 10) because of their resonance stabilized conjugate base, phenoxide.  Alcohols are considered neutral with pKa values similar to water (pKa = 14). The concepts used to predict relative acidity are explained in Chapter 1.
    • 13.6: Synthesis of Alcohols - Review
      Through the first ten chapters, we have learned to synthesize alcohols from alkyl halides via nucleophilic substitution (SN2 & SN1) and from alkenes using a variety of pathways determined by regiochemistry and stereochemistry.  Gentle oxidation of the alkenes can also be used to synthesize diols.
    • 13.7: Reduction of the Carbonyl Group - Synthesis of 1º and 2º Alcohols
      Aldehydes, ketones, carboxylic acids, and esters can all be reduced to form alcohols.  An important pattern of chemical reactivity is introduced when we notice that aldehydes and ketones often use the same reagents, where as carboxylic acids and esters require different reagents to create similar reactivity.
    • 13.8: Organometallic Reagents
      Grignard (RMgX) and organolithium (RLi) reagents are made from alkyl halides in aprotic solvents.
    • 13.9: Organometallic Reagents in Alcohol Synthesis
      Organometallic reagents can react with aldehydes, ketones, acyl halides, esters, and epoxides to synthesize alcohols with an increased number of carbon atoms in the product.  Building larger organic molecules is a useful skill for multi-step synthesis.
    • 13.10: Thiols (Mercaptans)
      Thiols are the sulfur-analogs to alcohols.  The major difference is the larger atomic size of sulfur relative to oxygen which creates differences in relative acidity and effectiveness as nucleophiles.
    • 13.11: Commercially Important Alcohols
      Both industrial and fermentation processes for alcohol synthesis are discussed.
    • 13.12 Additional Exercises
      This section has additional exercises for the key learning objectives of the chapter.
    • 13.13: Solutions to Additional Exercises
      This section has the solutions to the Additional Practice Problems in the previous section.