Special Introduction to Chapter

For the most part, and as the hydroxyl (-OH) functional group is more common, alcohols will receive greater emphasis in this chapter. However, to the extent that similarities and differences between, for example, alcohols and thiols, and alcohols and ethers can be drawn upon for emphasis, and to the extent that some ofi in par- 

Foundations of Organic Chemistry Unity and Diversity of Structures, Pathways, and Reactions, First Edition. David R. Dalton. 

TTie use of alcohols (R-OH R H) and ethers (R-O-R R, R H) as solvents and (for the former) reactants was also pointed out in Chapters 5-7. Additionally, as has already been mentioned and as will be discussed further, alcohols (R-OH R H) and ethers (R-O-R R, R H), much like water (R-OH R = H), can be protonated (they are basic) by strong acid and, for the former, deprotonated (they are acidic) by strong bases. 

As shown in Table 8.1, the preparation of some alcohols (with one or more hydroxyl [-OH] groups) has been provided earlier. Table 8.2 reminds the reader that (a) enols are in equilibrium with their corresponding carbonyl tautomers (Chapter 5) (b) acid-catalyzed addition of alcohols (R-OH R H) and thiols (R-SH R H) to, for example, alkenes can be used to produce ethers (R-O-R R, R H) and thioethers (R-S-R R, R H), respectively (Chapter 6) (c) ethers are readily formed by nucleophilic substitution of halogen (X = Cl, Br, I) by alkoxide (RO ) (Chapter 7) under the appropriate (SnI or Sn2) conditions and (d) substitution of a halogen on an aromatic ring (Ar-X, X = Cl, Br) can be effected by fusion with molten alkali (e.g., NaOH) (Chapter 7). 

TABLE 8.1. Examples of Some of the Reactions That Produce Alcohols and That Have Been Encountered in Previous Chapters 

---