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13: Alcohols and Phenols

Last updated

Jun 23, 2019
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- 12.E: Synthesis (Exercises)
- 13.1: Physical Properties of Alcohols; Hydrogen Bonding

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Topic hierarchy

13.1: Physical Properties of Alcohols; Hydrogen Bonding
Comparison of the physical properties of alcohols with those of hydrocarbons of comparable molecular weight shows several striking differences, especially for those with just a few carbons. Alcohols are substantially less volatile, have higher melting points, and greater water solubility than the corresponding hydrocarbons, although the differences become progressively smaller as molecular weight increases.
13.2: Preparation of Alcohols via Reduction
13.3: Preparation of Diols
13.4: Reactions of Alcohols - Substitution and Elimination
13.5: Reactions of Alcohols- Oxidation
13.6: Biological Redox Reactions
13.7: Oxidation of Phenol
13.8: Synthesis Strategies
13.9: Physical Properties of Alcohols; Hydrogen Bonding
Comparison of the physical properties of alcohols with those of hydrocarbons of comparable molecular weight shows several striking differences, especially for those with just a few carbons. Alcohols are substantially less volatile, have higher melting points, and greater water solubility than the corresponding hydrocarbons, although the differences become progressively smaller as molecular weight increases.
13.10: 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 = 16). The concepts used to predict relative acidity are explained in Chapter 1.
13.11: 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.
13.12: 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.
13.13: 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.
13.14: Alcohols from Reaction of Carbonyl Compounds- Grignard Reagents
13.15: 13.7 Reactions of Alcohols
13.16: 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.
13.17: 13.9 Alcohols from Carbonyl Compounds- Reduction
13.E: Alcohols and Phenols (Exercises)

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