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Alcohols, Ethers, and Thiols

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Alcohols, Ethers, and Thiols 08 Alcohols, Ethers, and Thiols An anesthesiologist administers isoflurane to a patient before surgery. The discovery that inhaling ethers could make a patient insensitive to pain revolutionized the practice of medicine. Inset: A model of isoflurane, CF3CHClOCHF2, a halogenated ether widely used as an inhalation anesthetic in both human and veterinary medicine. (Alan Levenson/Stone/Getty Images) KEY QUESTIONS 8.1 What Are Alcohols? 8.3 How to Predict the Position of Equilibrium of an 8.2 What Are the Characteristic Reactions of Alcohols? Acid–Base Reaction 8.3 What Are Ethers? 8.4 How to Complete a Dehydration Reaction 8.4 What Are Epoxides? 8.5 How to Predict the Product of an Epoxidation Reaction 8.5 What Are Thiols? 8.6 What Are the Characteristic Reactions of Thiols? CHEMICAL CONNECTIONS 8A Nitroglycerin: An Explosive and a Drug HOW TO 8B Blood Alcohol Screening 8.1 How to Name Cyclic Alcohols 8C Ethylene Oxide: A Chemical Sterilant 8.2 How to Predict Relative Boiling Points of Compounds of Similar Molecular Weight IN THIS CHAPTER, we study the physical and chemical properties of alcohols and ethers, two classes of oxygen-containing compounds we have seen as products of chemical reac- tions (Sections 5.3B and 7.4). We also study thiols, a class of sulfur-containing compounds. Thiols are like alcohols in structure, except that they contain an J SH group rather than an J OH group. 239 240 CHAPTER 8 Alcohols, Ethers, and Thiols CH3CH2OH CH3CH2OCH2CH3 CH3CH2SH Ethanol Diethyl ether Ethanethiol (an alcohol) (an ether) (a thiol) These three compounds are certainly familiar to you. Ethanol is the fuel additive in gaso- line, the alcohol in alcoholic beverages, and an important industrial and laboratory solvent. Diethyl ether was the first inhalation anesthetic used in general surgery. It is also an important industrial and laboratory solvent. Ethanethiol, like other low-molecular-weight thiols, has a stench. Smells such as those from skunks, rotten eggs, and sewage are caused by thiols. Alcohols are particularly important in both laboratory and biochemical transformations of organic compounds. They can be converted into other types of compounds, such as al- kenes, haloalkanes, aldehydes, ketones, carboxylic acids, and esters. Not only can alcohols be converted to these compounds, but they also can be prepared from them. Thus, alcohols play a central role in the interconversion of organic functional groups. 8.1 What Are Alcohols? A. Structure Alcohol A compound The functional group of an alcohol is an J OH (hydroxyl) group bonded to an sp3 hybrid- containing an J OH ized carbon atom (Section 1.7A). The oxygen atom of an alcohol is also sp3 hybridized. Two (hydroxyl) group bonded to sp3 hybrid orbitals of oxygen form sigma bonds to atoms of carbon and hydrogen. The other an sp3 hybridized carbon. two sp3 hybrid orbitals of oxygen each contain an unshared pair of electrons. Figure 8.1 shows a Lewis structure and ball-and-stick model of methanol, CH3OH, the simplest alcohol. (a) H O B. Nomenclature H C H We derive the IUPAC names for alcohols in the same manner as those for alkanes, with the exception that the ending of the parent alkane is changed from -e to -ol. The ending -ol tells H us that the compound is an alcohol. 1. Select, as the parent alkane, the longest chain of carbon atoms that contains the J OH, (b) and number that chain from the end closer to the J OH group. In numbering the parent chain, the location of the J OH group takes precedence over alkyl groups and halogens. 108.6 2. Change the suffix of the parent alkane from -e to -ol (Section 3.5), and use a number 108.9 to show the location of the J OH group. For cyclic alcohols, numbering begins at the carbon bearing the J OH group. 109.3 3. Name and number substituents and list them in alphabetical order. FIGURE 8.1 To derive common names for alcohols, we name the alkyl group bonded to J OH Methanol, CH3OH. (a) Lewis and then add the word alcohol. Following are the IUPAC names and, in parentheses, the structure and (b) ball-and- common names of eight low-molecular-weight alcohols: stick model. The measured H J O J C bond angle in OH methanol is 108.6°, very close to the tetrahedral OH angle of 109.5°. OH OH Ethanol 1-Propanol 2-Propanol 1-Butanol (Ethyl alcohol) (Propyl alcohol) (Isopropyl alcohol) (Butyl alcohol) OH OH OH OH 2-Butanol 2-Methyl-1-propanol 2-Methyl-2-propanol Cyclohexanol (sec -Butyl alcohol) (Isobutyl alcohol) (tert -Butyl alcohol) (Cyclohexyl alcohol) 8.1 What Are Alcohols? 241 Name Cyclic Alcohols (a) First, determine the root name of the cycloalkane, and replace the suffix -e with -ol. OH 8.1 the root name of a 5-carbon ring is because it’s an alcohol, CH3 “cyclopentane” the -e in cyclopentane is replaced with -ol CH3CH2 Cyclopentanol HOW TO (b) Name and number the substituents. Numbering begins at the carbon bear- ing the J OH group and proceeds in the direction that gives the lowest total for all substituents. the numbering system in blue + + = (1 2 4 7) gives a lower total than + + = the numbering system in red (1 3 5 9) numbering begins OH at the carbon ¬ 1 bearing the OH 1 CH 5 2 5 3 2 a methyl group 4 3 4 3 CH3CH2 an ethyl group (c) Place substituents in alphabetical order preceded by its position on the ring. Position 1 for the J OH group is assumed. OH 1 5 CH3 2 4 3 CH3CH2 4-Ethyl-2-methylcyclopentanol (d) Don’t forget to indicate stereochemistry. OH (R) 1 CH 5 3 2 (S) (S) 4 3 CH3CH2 (1R,2S,4S)-4-Ethyl-2-methylcyclopentanol EXAMPLE 8.1 Write the IUPAC name for each alcohol: OH OH (a) CH3(CH2)6CH2OH (b) (c) 242 CHAPTER 8 Alcohols, Ethers, and Thiols STRATEGY First look for the longest chain of carbons that contains the J OH group. This will allow you to determine the root name. Then identify the atoms or groups of atoms that are not part of that chain of carbons. These are your substituents. SOLUTION (a) 1-Octanol (b) 4-Methyl-2-pentanol (c) trans-2-Methylcyclohexanol or (1R,2R)-2-Methylcyclohexanol See problems 8.14, 8.15, 8.17 PROBLEM 8.1 Write the IUPAC name for each alcohol: OH OH (a) (b) OH (c) We classify alcohols as primary (1), secondary (2), or tertiary (3), depend- ing on whether the J OH group is on a primary, secondary, or tertiary carbon (Section 1.7A). EXAMPLE 8.2 Classify each alcohol as primary, secondary, or tertiary: STRATEGY OH Determine how many carbons are bonded to the carbon CH3 bonded to the J OH group (1 carbon 1°, 2 carbons 2°, and 3 carbons 3°). (a) (b) CH3COH CH3 SOLUTION (a) Secondary (2°) (b) Tertiary (3°) (c) Primary (1°) CH2OH (c) See problem 8.13 PROBLEM 8.2 Classify each alcohol as primary, secondary, or tertiary: OH OH OH (a) (b) (c) CH2“CHCH2OH (d) In the IUPAC system, a compound containing two hydroxyl groups is named as a diol, one containing three hydroxyl groups is named as a triol, and so on. In IUPAC names for diols, triols, and so on, the final -e of the parent alkane name is retained, as for example, in 1,2-ethanediol. 8.1 What Are Alcohols? 243 As with many organic compounds, common names for certain diols and triols have Glycol A compound persisted. Compounds containing two hydroxyl groups on different carbons are often with two hydroxyl ( J OH) groups on different carbons. referred to as glycols. Ethylene glycol and propylene glycol are synthesized from ethylene and propylene, respectively—hence their common names: CH CH CH CHCH CH CHCH ƒ 2 ƒ 2 3 ƒ ƒ 2 ƒƒ2 ƒ 2 OH OH HO OH HO HO OH 1,2-Ethanediol 1,2-Propanediol 1,2,3-Propanetriol Charles D. Winters (Ethylene glycol) (Propylene glycol) (Glycerol, Glycerin) Ethylene glycol is a polar molecule and dissolves readily in water, a polar solvent. ChemicalCheChmical i l ConnectionsConnect io ns 8A NITROGLYCERIN: AN EXPLOSIVE AND A DRUG In 1847, Ascanio Sobrero (1812–1888) discovered The fortune of Alfred that 1,2,3-propanetriol, more commonly named Nobel, 1833–1896, built glycerin, reacts with nitric acid in the presence of on the manufacture of sulfuric acid to give a pale yellow, oily liquid called dynamite, now funds nitroglycerin: the Nobel Prizes. CH2 J OH CH2 J ONO2 H2SO4 CH J OH 3HNO3 CH J ONO2 3H2O CH2 J OH CH2 J ONO2 1,2,3-Propanetriol 1,2,3-Propanetriol trinitrate (Glycerol, Glycerin) (Nitroglycerin) Sobrero also discovered the explosive properties of Bettmann/Corbis the compound: When he heated a small quantity of it, © it exploded! Soon, nitroglycerin became widely used for blasting in the construction of canals, tunnels, it nonexplosive), tablet, or paste form, relaxes the roads, and mines and, of course, for warfare. smooth muscles of blood vessels, causing dilation of One problem with the use of nitroglycerin was the coronary artery. This dilation, in turn, allows more soon recognized: It was difficult to handle safely, and blood to reach the heart. accidental explosions occurred frequently. The Swed- When Nobel became ill with heart disease, his ish chemist Alfred Nobel (1833–1896) solved the prob- physicians advised him to take nitroglycerin to re- lem: He discovered that a claylike substance called lieve his chest pains. He refused, saying he could not diatomaceous earth absorbs nitroglycerin so that it understand how the explosive could relieve chest will not explode without a fuse.
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