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    16 Alcohols: Reactions

    and Synthesis

    Citronellol

    16.1 Alcohols can be converted into many classes of oxygen-containing compounds including ethers,
    OVERVIEW OF esters, aldehydes, ketones, and carboxylic acids. They can also be converted into haloalkanes by
    substitution reactions, and into alkenes by elimination reactions.
    ALCOHOL REACTIONS We will classify the reactions of alcohols by the bonds that are formed or broken. Considering
    only the bonds of the hydroxyl oxygen atom, two types of reactions occur: the O—H bond can break
    or the C—O bond can break. We have already considered the loss of a proton from the O—H bond
    in acid–base reaction. Acid-base reactions are not synthetic reactions. However, replacing the hydrogen
    atom of the O—H bond by a carbon-containing group is a synthetic procedure used to form more
    complex structures.
    H H The carbon-oyxgen bond breaks in a nucleophilic
    C C O substitution reaction, which is often acid-catalyzed.

    The reaction of the oxygen atom with the electrophilic center of alkyl groups bonded to good leaving
    groups yields ethers. We will discuss the synthesis of ethers in Chapter 17. Many of the reactions of
    alcohols yield an ester either as a reaction intermediate or as a stable product. Ester-forming reac-
    tions fall into three broad classes:

    1. The synthesis of esters of inorganic or organic acids.

    2. The formation of ester intermediates that contain a transition metal.

    3. The formation of ester intermediates in the conversion of alcohols into alkyl halides.

    We will begin with a brief review of the conversion of alcohols into alkyl halides that we discussed in
    Chapter 9. The conversion of alcohol to alkyl chlorides and alkyl bromides is accomplished using thio-
    nyl chloride and phosphorus tribromide, respectively. The C—O bond breaks in these nucleophilic
    substitution reactions.

    H H

    C C O Replacing the alcohol hydrogen with an alkyl group gives an ether.


    Replacing it with a carbonyl carbon atom yields an ester.
    H

    In some reactions in which either the C—O or the O—H bond breaks, a C—H bond also breaks.
    That C—H bond may be on the b carbon atom or on the atom bearing the hydroxyl group. The de-
    hydration reaction of alcohols results in the cleavage of both the C—O bond and the C—H bond of
    the β carbon atom. We discussed this process, a β-elimination reaction that results in net dehydration,
    in Section 9.20.

    Organic Chemistry. https://doi.org/10.1016/B978-0-12-812838-1.50016-5 Copyright © 2018 Elsevier Inc. All rights reserved. 463

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