ALCOHOLS, DIOLS, AND THIOLS

1 The two primary alcohols, 1-butanol and 2-methyl-1-propanol, can be prepared by hydrogenation of the corresponding aldehydes. 

The secondary alcohol 2-butanol arises by hydrogenation of a ketone. 

Tertiary alcohols such as 2-methyl-2-propanol, (CH3)3COH, cannot be prepared by hydrogenation of a carbonyl compound. 

2 (b) A deuterium atom is transferred from NaBD4 to the carbonyl group of acetone. 

On reaction with CH3OD, deuterium is transferred from the alcohol to the oxygen of [(CH3)2CDO]4B. 

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The next several chapters deal with the chemistry of various oxygen-containing functional groups. The interplay of these important classes of compounds—alcohols, ethers, aldehydes, ketones, carboxylic acids, and derivatives of carboxylic acids—is fundamental to organic chemistry and biochemistry. 

WeTl start by discussing in more detail a class of compounds already familiar to us, alcohols. Alcohols were introduced in Chapter 4 and have appeared regularly since then. With this chapter we extend our knowledge of alcohols, particularly with respect to their relationship to carbonyl-containing compounds. In the course of studying alcohols, we shall also look at some relatives. Diols are alcohols in which two hydroxyl groups (—OH) are present thiols are compounds that contain an —SH group. Phenols, compounds of the type ArOH, share many properties in common with alcohols but are sufQciently different from them to warrant separate discussion in Chapter 24. 

This chapter is a transitional one. It ties together much of the material encountered earlier and sets the stage for our study of other oxygen-containing functional groups in the chapters that follow. 

Until the 1920s, the major source of methanol was as a byproduct in the production of charcoal from wood—whence, the name wood alcohol. Now, most of the more than 10 

Carbon monoxide is obtained from coal, and hydrogen is one of the products formed when natural gas is converted to ethylene and propene (Section 5.1). 

Sodium Borohydride Reduction of an Aldehyde or Ketone 653 Acid-Catalyzed Formation of Diethyl Ether from Ethyl Alcohol 660 Chromic Acid Oxidation of 2-Propanol 665 

Dimethyl Sulfoxide Oxidation of an Alcohol (Swern Oxidation) 666 Oxidation of Ethanol by NAD 669 

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