Structure and Synthesis of Alcohols

Alcohols are synthesized by a wide variety of methods, and the hydroxyl group may be converted to most other functional groups. For these reasons, alcohols are versatile synthetic intermediates. In this chapter, we discuss the physical properties of alcohols and summarize the methods used to synthesize them. In Chapter 11 (Reactions of Alcohols), we continue our study of the central role that alcohols play in organic chemistry as reagents, solvents, and synthetic intermediates. 

One way of organizing the alcohol family is to classify each alcohol according to the type of carbinol carbon atom the one bonded to the —OH group. If this carbon atom is primary (bonded to one other carbon atom), the compound is a primary alcohol. A secondary alcohol has the — OH group attached to a secondary carbon atom, and a 

Compounds with a hydroxyl group bonded directly to an aromatic (benzene) ring are called phenols. Phenols have many properties similar to those of alcohols, while other properties derive from their aromatic character. In this chapter, we consider the properties of phenols that are similar to those of alcohols and note some of the differences. In Chapter 16, we consider the aromatic nature of phenols and the reactions that result from that aromaticity. 

Classification of alcohols. Alcohols are classified according to the type of carbon atom (primary, secondary, or tertiary) bonded to the hydroxyl group. Phenols have a hydroxyl group bonded to a carbon atom in a benzene ring. 

The lUPAC system provides unique names for alcohols, based on rules that are similar to those for other classes of compounds. In general, the name carries the -ol suffix, together with a number to give the location of the hydroxyl group. The formal rules are summarized in the following three steps  

10-1 Please seethe note on p. 136 of this Solutions Manual regarding placement of position numbers. 

10-2 IUPAC name first, then common name. 

10-3 Only constitutional isomers are requested, not stereoisomers, and only structures with an alcohol group. 

10-7 See Appendix 2 at the back of this Solutions Manual for a review of acidity and basicity. 

10-9 Resonance forms of phenoxide anion show the negative charge delocalized onto the ring only at carbons 2, 4, and 6  

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