13: Properties and Reactions of Alcohols
- Page ID
- 391412
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- 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: 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.
- 13.6: 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.
- 13.7: 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: Additional Exercises Part 1
- This section has additional exercises for the key learning objectives of the chapter.
- 13.11: Solutions to Additional Exercises Part 1
- This section has the solutions to the Additional Practice Problems in the previous section.
- 13.12: Reactions of Alcohols with Hydrohalic Acids
- Alcohols react with hydrohalic acids (HCl, HBr, and HI) to form alkyl halides via the SN1 or SN2 mechanism as determined by the structure of the alcohol. Since hydroxide is a poor leaving group, acid catalysis is required.
- 13.13: Reactions with Phosphorus Halides and Thionyl Chloride
- Because of the limited synthetic utility of reacting alcohols with hydrohalic acids to form alkyl halides, the alternative reagents thionyl chloride and phosphorous tribromide. have been developed.
- 13.14: Dehydration Reactions of Alcohols
- Alcohols can form alkenes via the E1 or E2 pathway depending on the structure of the alcohol and the reaction conditions. Markovnokov's Rule still applies and carbocation rearrangements must be considered for the E1 mechanism.
- 13.15: Oxidation States of Alcohols and Related Functional Groups
- Organic chemistry requires an expanded definition of oxidation and reduction.
- 13.16: Oxidation Reactions of Alcohols
- Alcohols can be oxidized using acidified sodium or potassium dichromate(VI) solution. This reaction has been used historically as a way of distinguishing between primary, secondary and tertiary alcohols.
- 13.17: Protection of Alcohols
- During the synthesis of complex molecules, one functional group may interfere or complete with the reagent intended for a second functional group on the same molecule. There are several methods for protecting and subsequently recovering alcohols during multiple step syntheses of complex molecules.
- 13.18: Additional Exercises Part 2
- This section has additional exercises for the key learning objectives of the chapter.
- 13.19: Solutions to Additional Exercises Part 2
- This section has the solutions to the additional exercises from the previous section.