7.2: Alcohols and Phenols- ROH, ArOH

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1. By the IUPAC system, the suffix -ol for \(OH\) is added to the name of the parent hydrocarbon. Notice that alkane \(+\) -ol becomes alkanol, with the e omitted:

Left: C L C H 2 C H 2 C H 2 O H. Labeled 3-chloro-1-propanol. Middle: Benzene ring with a C H 2 O H substituent. Labeled phenylmethanol (benzyl alcohol). Right: Cyclohexane with two O H substituents on carbons 1 and 4. Labeled 1,4-cyclohexanediol.

2. The substituent name for the \(OH\) group is hydroxy and should be used whenever the \(OH\) group is not the parent function (see Table 7-1). Notice how the precedence rules apply - hydroxy below carboxylic acid and hydroxy below ketone:

Left: H O C H 2 C O 2 H. Labeled hydroxyethanoic acid (hydroxyacetic acid). Right: H O C H 2 C. Rightmost carbon single bonded to C H 3 and double bonded to O. Labeled hydroxy-2-propanone (hydroxyacetone).

3. Many trivial names persist, particularly for aromatic, or arene alcohols (phenols):

Left: benzene with O H substituent on top carbon. Labeled benzenol (phenol). Middle: benzene ring with an O H substituent on carbon 1 and a C H 3 substituent on carbon 3. Labeled 3-methylbenzenol (meta-cresol). Right: benzene ring with O H substituents on carbons 1 and 4. Labeled 1,4-benzendiol (hydroquinone).

Contributors and Attributions

John D. Robert and Marjorie C. Caserio (1977) Basic Principles of Organic Chemistry, second edition. W. A. Benjamin, Inc. , Menlo Park, CA. ISBN 0-8053-8329-8. This content is copyrighted under the following conditions, "You are granted permission for individual, educational, research and non-commercial reproduction, distribution, display and performance of this work in any format."