orgo 10 - Fermentation vats of wine grapes at the Beaulieu...

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1 Fermentation vats of wine grapes at the Beaulieu Vineyards, California. Inset: a model of ethanol OUTLINE Structure and Nomenclature of Alcohols Physical Properties of Alcohols Acidity and Basicity of Reaction of Alcohols with Active Metals Conversion of Alcohols to Haloalkanes and Sulfonates Acid-Catalyzed Dehydration of Alcohols The Pinacol Rearrangement Oxidation of Alcohols Thiols ti,:iOnline homework for this chapter may be assigned in Organic OWL. I n this chapter, we study the physical and chemical properties of alcohols, a class of compounds containing the -OH (hydroxyl) group. We also study thiols, a class of compounds containing the -SH (sulfhydryl) group. CH 3 CH 2 0H Ethanol Ethanethiol (an alcohol) (a thiol) Ethanol is the additive in E85, the alcohol in alcoholic beverages, and an impor- tant industrial solvent. Ethanethiol, like all other low-molecular-weight thiols, has a stench; such smells from skunks, rotten eggs, and sewage are caused by thiols or H 2 S. Alcohols are important because they can be converted into many other types of compounds, including alkenes, haloalkanes, aldehydes, ketones, carboxylic acids, and esters. Not only can alcohols be converted to these compounds, but these compounds can also be converted to alcohols. Thus, alcohols playa central role in the interconversion of organic functional groups. Hydroxyl groups are found in carbohydrates and certain amino acids. Following are two representations for glucose, the most abundant organic compound in na- ture. On the left is a Fischer projection sho\o\ring the configuration of all chiral cen- ters. On the right is a cyclic structure, the predominant form in which this molecule exists in both the solid form and in solution. The amino acid L-serine is one of the 20 amino acid building blocks of proteins. 374 Chapter 10
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H±CHO OH HO H HOjCOO- H H NH + 3 CH 2 0H D-Glucose ,B-D-Glucopyranose L-Serine (Fischer projection) Because sulfur and oxygen are both Group 6 elements, thiols and alcohols un- iergo many of the same types of reactions. Sulfur, a third-row element, however, ~n undergo some reactions that are not possible for alcohols. In addition, sulfur's ~Iectronegativity and basicity are less than those of oxygen. 10.1 Structure and Nomenclature of Alcohols A. Structure The functional group of an alcohol is an -OR (hydroxyl) group (Section 1.3A) onded to an sf-hybridized carbon. The oxygen atom of an alcohol is also sl; ~vbridized. Two sji' hybrid orbitals of oxygen form (T bonds to atoms of carbon ~nd hydrogen, and the remaining two sfrq hybrid orbitals each contain an unshared :nair of electrons. Figure 10.1 shows a Lewis structure and a baU-and-stick model of :nethanol, CH 3 0H, the simplest alcohol. The measured C-O-H bond angle in :nethanol is 108.9°, very close to the perfectly tetrahedral angle of 109.5°. B. Nomenclature the IUPAC system, the longest chain of carbon atoms containing the -OH group is selected as the parent alkane and numbered from the end closer to -OH. To ,how that the compound is an alcohol, change the suffix -e of the parent alkane to -01 (Section 2.3), and use a number to show the location of the
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orgo 10 - Fermentation vats of wine grapes at the Beaulieu...

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