Structure and nomenclature of alcohols

Structure and Classification of Alcohols 425 10-3 Nomenclature of Alcohols and Phenols 427 10-4 Physical Properties of Alcohols 430 10-5 Commercially Important Alcohols 433 10-6 Acidity of Alcohols and Phenols 435 10-7 Synthesis of Alcohols Introduction and Review 438 Summary Previous Alcohol Syntheses 438 10-8 Organometallic Reagents for Alcohol Synthesis 440 10-9 Addition of Organometallic Reagents to Carbonyl Compounds 443... 

The structure and nomenclature of sulfonate esters (see 113, 114, or 115) are described in Chapter 20 (Section 20.11.2). It is also true that sulfonate esters are good leaving groups in the substitution reactions described in this chapter (see Section 11.2.4). Sulfonate esters are prepared by the reaction of sulfonic acids with alcohols—much the way that carboxylic acid esters are prepared from carboxylic acids and alcohols (described in Chapter 20, Section 20.11.2). More commonly, sulfonate esters are prepared by the reaction of a sulfonyl chloride (see 112) with an alcohol. This reaction is also described in Chapter 20. This section presents only a simple preview of that chemistry, with the goal of showing that it is easy to convert alcohols into sulfonate esters, which are then useful as leaving groups in substitution reactions. The formal mechanism of these reactions will be discussed in Chapter 20. 

We begin by bringing you up to speed on mechanisms and reminding you how to push electrons around with those curved arrows. We jog your memory with a discussion of substitution and elimination reactions and their mechanisms, in addition to free radical reactions. Next you review the structure, nomenclature, synthesis, and reactions of alcohols and ethers, and then you get to tackle conjugated unsaturated systems. Finally, we remind you of spectroscopic techniques, from the IR fingerprints to NMR shifts. The review in this part moves at a pretty fast pace, but we re sure you can keep up. 

Production of phenol and acetone is based on liquid-phase oxidation of isopropylbenzene. Synthetic fatty acids and fatty alcohols for producing surfactants, terephthalic, adipic, and acetic acids used in producing synthetic and artificial fibers, a variety of solvents for the petroleum and coatings industries—these and other important products are obtained by liquid-phase oxidation of organic compounds. Oxidation processes comprise many parallel and sequential macroscopic and unit (or very simple) stages. The active centers in oxidative chain reactions are various free radicals, differing in structure and in reactivity, so that the nomenclature of these labile particles is constantly changing as oxidation processes are clarified by the appearance in the reaction zone of products which are also involved in the complex mechanism of these chemical conversions. 

The common name of an alcohol is derived from the common name of the alkyl group and the word alcohol. This system pictures an alcohol as a molecule of water with an alkyl group replacing one of the hydrogen atoms. If the structure is complex, the common nomenclature becomes awkward, and the IUPAC nomenclature should be used. 

The nomenclature of starch components has become highly confused through the indiscriminate use of such terms as a and /3-amylose, amylose and amylopectin, amyloamylose and erythroamylose, etc. It does not seem advisable to apply any of these older terms to the new and unique fractions obtained by selective precipitation methods. It is therefore proposed that the term A-fraction be applied to that portion of the starch which is preferentially precipitated by various alcohols or by higher fatty acids, and which exhibits a high affinity for iodine. Correspondingly, the residual non-precipitated portion of the starch, which possesses low iodine affinity, is termed the B-fraction. These designations apply to laboratory-prepared samples, and do not carry any a priori connotations of purity, homogeneity, or structure. 

The nomenclature of esters is relatively simple, because it is similar to the nomenclature of salts. For instance, the ester obtained from methanol and ethanoic acid (acetic acid) is called methyl ethanoate (methyl acetate). Esters are compounds that comprise a large number of structures depending on what the alcohol and acid components are. Esters with a small molecular mass are volatile substances, in most cases with a pleasant odor. For instance, butyl acetate is responsible for the odor of apples. In nature, some esters serve as pheromones for insects, for example isoamyl acetate which attracts butterflies. Other kinds of esters can be large molecules as for instanee waxes and fats where both the alcohol and the acid components can be long-ehained or eomplicated structures. These natural esters will be diseussed in the ehapter on lipids. In industry, esters are used in the fabrication of polymeric fibers for textile materials and plastic materials for various uses. The most common material is polyethylene terephthalate (PET), the ester prepared from terephthalic acid and ethylene glycol. 

WL Interactive versions of these problems are assignable in OWL. Nomenclature and Structure of Alcohols... 

The crystalline phases consist of stacked bilayers of alcohol molecules, which are either in a tilted (y) or perpendicular orientation (a and P) with respect to the plane of the bilayers. A similar stacking of bilayers is found in lamellar liquid crystals but in this case the structure is swollen in a one-dimensional fashion by water and/or oil. Depending on whether the surfactant and cosurfactant chains are in a conformationally disordered molten or an extended rigid state, the lyotropic liquid crystalline phase is called L or phase, respectively. The phase is also known as gel phase. This nomenclature is also used for lipids. Concerning the sur-factant/fatty alcohol/water systans considered here, it must be pointed out that the swelling of a crystals with water results in an Lp phase. 

Sulfur is in the same group of the periodic table as oxygen and forms compounds structurally similar to alcohols. Compounds containing an —SH group, called a sulfhydryl group, are named as mer-captans or thiols. The nomenclature of these compounds resembles that of alcohols, except that the suffix - thiol replaces the suffix -ol and the -e of the alkane name is retained. 

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