Naming the Alcohols

Like other compounds, alcohols may have both systematic and common names. Systematic nomenclature treats alcohols as derivatives of alkanes. The ending -e of the alkane is replaced by -ol. Thus, an alkane is converted into an alkanol. For example, the simplest alcohol is derived from methane methanol. Ethanol stans from ethane, propanol from propane, and so on. In more complicated, branched systans, the name of the alcohol is based on the longest chain containing the OH substituent— not necessarily the longest chain in the molecule. 

Note In acyclic alkanols, the OH-bearing carbon receives the number 1 only when it is located at the end of the stem chain. 

Cyclic alcohols are called cycloalkanols. Here the carbon carrying the functional group 

When named as a substituent, the OH group is called hydroxy. This occurs when a functional group taking higher precedence, such as in hydroxycarboxylic acids, is present (see margin structure). Like haloalkanes, alcohols can be classified as primary, secondary, or tertiary. 

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The classic definition of asphaltenes is based on the solution properties of petroleum residua in various solvents. The word asphaltene was coined in France by J.B. Boussingault in 1837. Boussingault described the constituents of some bitumens (asphalts) found at that time in eastern France and in Peru. He named the alcohol insoluble, essence of turpentine soluble solid obtained from the distillation residue "asphaltene", since it resembled the original asphalt. 

Octyl formate has the flavor of oranges. Name the alcohol and the carboxylic acid needed to synthesize this ester. 

Write the structural formulas for the alcohol and the carboxylic acid that react to form it. Name the alcohol, (b) Suppose that the carboxylic acid from part (a) is changed chemically so that the OCH3 group is replaced by a hydrogen atom and the COOH group is replaced by a CH3 group. Name the hydrocarbon that would result. 

C6H13OH. (6) Name the alcohols according to the two methods explained in section 78. (c) Indicate which of the alcohols have the primary, secon-... 

The chromic acid in pyridine oxidation of dihydroschizozygine yielded products (Chart VI) important in the structural elucidation, namely, the alcohol (oxidation at the benzyl carbon, C-7 mp 187°-188° [a]j, +30°inCHCl3 piL 4.96) and the unsaturated amide, XL (mp 315°-316° [a]j3 +40° in CHCI3) long wavelength absorption maximum at 380 nm (log e 4.17). An examination of the products formed in the Hofmann degradation of schizozygine methiodide also led to the conclusion that there was a proton attached to C-7 (Chart VI). 

Aside from lUPAC names, the simple alcohols (one to four carbons) are also known by common names. The alcohol is named by naming the alkyl substituent attached to the OH group followed by the word alcohol. 

Multimodal porous systems in the form of monolithic-shaped forms (bodies) were obtained from a process where a (true) liquid-crystal templating is combined with a sol-gel process [205]. One characteristic of such a process is the incompatibility of lyotropic surfactants with an alcohol, mostly an inherently produced alcohol, which is responsible for the phase separation during the sol-gel processing, stabilizing the resulting monolithic architecture of the monolith [206]. Different approaches use various components, namely, the alcohol source, the silicate sources (both are sometimes combined in one molecule), and molecular or supramolecular templating agents [207]. 

Where do we stand now, and where do we go from here With Chapter 8, we have begun to discuss a second important functional class of compounds after the haloalkanes, namely, the alcohols. We used the haloalkanes to introduce two major mechanistic pathways radical... 

Name the longest carbon chain attached to the —OH group by replacing the e in the corresponding alkane name with ol. To name the alcohol, the e in alkane name pentane is replaced with ol. 

A catalytic enantio- and diastereoselective dihydroxylation procedure without the assistance of a directing functional group (like the allylic alcohol group in the Sharpless epox-idation) has also been developed by K.B. Sharpless (E.N. Jacobsen, 1988 H.-L. Kwong, 1990 B.M. Kim, 1990 H. Waldmann, 1992). It uses osmium tetroxide as a catalytic oxidant (as little as 20 ppm to date) and two readily available cinchona alkaloid diastereomeis, namely the 4-chlorobenzoate esters or bulky aryl ethers of dihydroquinine and dihydroquinidine (cf. p. 290% as stereosteering reagents (structures of the Os complexes see R.M. Pearlstein, 1990). The transformation lacks the high asymmetric inductions of the Sharpless epoxidation, but it is broadly applicable and insensitive to air and water. Further improvements are to be expected. 

Functional class names of alcohols are derived by naming the alkyl group that bears the hydroxyl substituent (—OH) and then adding alcohol as a separate word The chain IS always numbered beginning at the carbon to which the hydroxyl group is attached... 

The substitutive names of alcohols are derived by replacing the e end mg of an alkane with ol The longest chain containing the OH group becomes the basis for the name Functional class names of alcohols begin with the name of the alkyl group and end m the word alcohol... 

Until the 1920s the major source of methanol was as a byproduct m the production of charcoal from wood—hence the name wood alcohol Now most of the more than 10 billion lb of methanol used annually m the United States is synthetic prepared by reduc tion of carbon monoxide with hydrogen... 

Acetaldehyde [75-07-0] (ethanal), CH CHO, was first prepared by Scheele ia 1774, by the action of manganese dioxide [1313-13-9] and sulfuric acid [7664-93-9] on ethanol [64-17-5]. The stmcture of acetaldehyde was estabhshed in 1835 by Liebig from a pure sample prepared by oxidising ethyl alcohol with chromic acid. Liebig named the compound "aldehyde" from the Latin words translated as al(cohol) dehyd(rogenated). The formation of acetaldehyde by the addition of water [7732-18-5] to acetylene [74-86-2] was observed by Kutscherow] in 1881. 

Esters are named by replacing the ending -ic acid with the suffix -ate. The alcohol portion of the ester is named by replacing the -ane ending of the parent hydrocarbon name with the suffix -yl. The alkyl radical name of an ester is separated from the carboxylate name, eg, methyl formate for HCOOCH. Amides are named by changing the ending -oic acid to -amide for either systematic or common names, eg, hexanamide and acetamide. 

The term still is applied only to the vessel in which liquids are boiled during distillation, but the term is sometimes applied to the entire apparatus, including the fractionating column, the condenser, and the receiver in which the distillate is collected. If a water and alcohol distillate is returned from the condenser and made to drip down through a long column onto a series of plates, and if the vapor, as it rises to the condenser, is made to bubble through this liquid at each plate, the vapor and liquid will interact so that some of the water in the vapor condenses and some of the alcohol in the liquid vaporizes. The interaction at each plate is equivalent to a redistillation. This process is referred to by several names in the industry namely rectification, fractionation, or fractional distillation. 

Nature produces a tremendous amount of methyl aleohol, simply by the fermentation of wood, grass, and other materials made to some degree of eellulose. In faet, methyl aleohol is known as wood aleohol, along with names sueh as wood spirits and methanol (its proper name the proper names of all aleohols end in -ol). Methyl aleohol is a eolorless liquid with a eharaeteristie aleohol odor. It has a flash point of 54°F, and is highly toxie. It has too many eommereial uses to list here, but among them are as a denaturant for ethyl alcohol (the addition of the toxie ehemieal methyl aleohol to ethyl aleohol in order to form denatured aleohol), antifreezes, gasoline additives, and solvents. No further substitution of hydroxyl radieals is performed on methyl aleohol. 

The substitution of one hydroxyl radical for a hydrogen atom in propane produces propyl alcohol, or propanol, which has several uses. Its molecular formula is C3H7OH. Propyl alcohol has a flash point of 77°F and, like all the alcohols, bums with a pale blue flame. More commonly known is the isomer of propyl alcohol, isopropyl alcohol. Since it is an isomer, it has the same molecular formula as propyl alcohol but a different structural formula. Isopropyl alcohol has a flash point of 53 F. Its ignition temperamre is 850°F, while propyl alcohol s ignition temperature is 700 F, another effect of the different stmcture. Isopropyl alcohol, or 2-propanol (its proper name) is used in the manufacture of many different chemicals, but is best known as rubbing alcohol. 

The amines are a group of compounds with the general formula R-NHj, and all the common amines are hazardous. As a class the amines pose more than one hazard, being flammable, toxic, and, in some cases, corrosive. The amines are an analogous series of compounds and follow the naming pattern of the alkyl halides and the alcohols that is, the simplest amine is methyl amine, with the molecular formula of CH NHj. Methyl amine is a colorless gas with an ammonia-like odor and an ignition temperature of 806°F. It is a tissue irritant and toxic, and it is used as an intermediate in the manufacture of many chemicals. Ethyl amine is next in the series, followed by propyl amine, isopropyl amine, butyl amine and its isomers, and so on. 

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