A-Hydroxyl alcohol

Functional group names are often incorporated into the common name of a compound. For example, a ketone might have a name that ends in one like acetone, and the name of a compound that contains a hydroxyl (alcohol or OH group) might end in ol (e.g., ethanol). The acyl group is the portion of the molecule that provides... 

Figure 15.6 A water molecule attacks the ester bond on a polylactic acid chain. It produces a carboxylic acid group (—COOH) and a hydroxyl alcohol group (—OH).

Figure 2.3 Scission of a PLA chain producing a carboxylic acid end group (R-COOH) and a hydroxyl alcohol end group (R -OH).

The method can be used to determine the amount of a known alcohol or phenol present in a crude sample, provided that the impurities do not themselves contain hydroxyl groups. 

This method is precisely similar to the previous method used for the estimation of the number of hydroxyl groups in a polyhydric alcohol. A known weight of aniline is heated with a mixture of acetic anhydride and pyridine until acetylation is complete the excess of acetic anhydride remaining is... 

Polyhydric alcohols are compounds containing two or more hydroxyl groups in the molecule. The two most important are ethylene glycol HOCHjCHjOH (a dihydric alcohol) and glycerol HOCHjCH(OH)CH. OH (a trihydric alcohol). Ethylene glycol may be obtained by the hydrolysis of ethylene dibromide or ethylene dichloride with dilute aqueous sodium hydroxide or sodium carbonate solution ... 

Dissolve 0-5 g. of the substance in 10 ml. of 50 per cent, alcohol, add 0-5 g. of solid ammonium chloride and about 0 -5 g. of zinc powder. Heat the mixture to boiling, and allow the ensuing chemical reaction to proceed for 5 minutes. Filter from the excess of zinc powder, and teat the filtrate with Tollen s reagent Section 111,70, (i). An immediate black or grey precipitate or a silver mirror indicates the presence of a hydroxyl-amine formed by reduction of the nitro compound. Alternatively, the filtrate may be warmed with Fehling s solution, when cuprous oxide will be precipitated if a hydroxylamine is present. Make certain that the original compound does not aflfect the reagent used. 

You also know how to make acids by FGl from a primary alcohol but an acid is itself a hydroxyl compound and can be disconnected in the same way as alcohols. What do you get if you do this ... 

Hydroxyl groups take precedence over ( outrank ) alkyl groups and halogen substituents m determining the direction m which a carbon chain is numbered The OH group is assumed to be attached to C 1 of a cyclic alcohol and is not numbered... 

The reaction of an alcohol with a hydrogen halide is a substitution A halogen usually chlorine or bromine replaces a hydroxyl group as a substituent on carbon Calling the reaction a substitution tells us the relationship between the organic reactant and its prod uct but does not reveal the mechanism In developing a mechanistic picture for a par ticular reaction we combine some basic principles of chemical reactivity with experi mental observations to deduce the most likely sequence of steps... 

The —OH proton of a primary alcohol RCH2OH is vicinal to two protons and its sig nal would be expected to be split into a triplet Under certain conditions signal splitting of alcohol protons is observed but usually it is not Figure 13 21 presents the NMR spec trum of benzyl alcohol showing the methylene and hydroxyl protons as singlets at 8 4 7 and 2 5 respectively (The aromatic protons also appear as a singlet but that is because they all accidentally have the same chemical shift and so cannot split each other)... 

Deuterium does not give a signal under the conditions of H NMR spectroscopy Thus replacement of a hydroxyl proton by deuterium leads to the disappearance of the OH peak of the alcohol Protons bonded to nitrogen and sulfur also undergo exchange with... 

With aldehydes, primary alcohols readily form acetals, RCH(OR )2. Acetone also forms acetals (often called ketals), (CH2)2C(OR)2, in an exothermic reaction, but the equiUbrium concentration is small at ambient temperature. However, the methyl acetal of acetone, 2,2-dimethoxypropane [77-76-9] was once made commercially by reaction with methanol at low temperature for use as a gasoline additive (5). Isopropenyl methyl ether [116-11-OJ, useful as a hydroxyl blocking agent in urethane and epoxy polymer chemistry (6), is obtained in good yield by thermal pyrolysis of 2,2-dimethoxypropane. With other primary, secondary, and tertiary alcohols, the equiUbrium is progressively less favorable to the formation of ketals, in that order. However, acetals of acetone with other primary and secondary alcohols, and of other ketones, can be made from 2,2-dimethoxypropane by transacetalation procedures (7,8). Because they hydroly2e extensively, ketals of primary and especially secondary alcohols are effective water scavengers. 

Esters. Most acryhc acid is used in the form of its methyl, ethyl, and butyl esters. Specialty monomeric esters with a hydroxyl, amino, or other functional group are used to provide adhesion, latent cross-linking capabihty, or different solubihty characteristics. The principal routes to esters are direct esterification with alcohols in the presence of a strong acid catalyst such as sulfuric acid, a soluble sulfonic acid, or sulfonic acid resins addition to alkylene oxides to give hydroxyalkyl acryhc esters and addition to the double bond of olefins in the presence of strong acid catalyst (19,20) to give ethyl or secondary alkyl acrylates. 

Polyol Esters. Polyol esters are formed by the reaction of an alcohol having two or more hydroxyl groups, eg, a polyhydric alcohol and a monobasic acid. In contrast to the diesters, the polyol in the polyol esters forms the backbone of the stmcture and the acid radicals are attached to it. The physical properties maybe varied by using different polyols or acids. Trimethylolpropane [77-99-6] C H O, and pentaerythritol [115-77-5] are... 

A nitro alcohol is formed when an ahphatic nitro compound with a hydrogen atom on the nitro-bearing carbon atom reacts with an aldehyde in the presence of a base. Many such compounds have been synthesized, but only those formed by the condensation of formaldehyde (qv) and the lower nitroparaffins (qv) are marketed commercially. The condensation may occur one to three times, depending on the number of hydrogen atoms on the nitro-substituted carbon (R and R = H or alkyl), and yield nitro alcohols with one to three hydroxyl groups. 

Displacement of a volatile with a nonvolatile alcohol is an important reaction for curing paint films with amino cross-linkers and amino resias on textile fabrics or paper. FoUowiag is an example of a methoxymethyl group on an amino resia reacting with a hydroxyl group of a polymer chain. 

Composition. Shellac is primarily a mixture of aUphatic polyhydroxy acids in the form of lactones and esters. It has an acid number of ca 70, a saponification number of ca 230, a hydroxyl number of ca 260, and an iodine number of ca 15. Its average molecular weight is ca 1000. Shellac is a complex mixture, but some of its constituents have been identified. Aleuritic acid, an optically inactive 9,10,16-trihydroxypalmitic acid, has been isolated by saponification. Related carboxyflc acids such as 16-hydroxy- and 9,10-dihydroxypalmitic acids, also have been identified after saponification. These acids may not be primary products of hydrolysis, but may have been produced by the treatment. Studies show that shellac contains carboxyflc acids with long methylene chains, unsaturated esters, probably an aliphatic aldehyde, a saturated aliphatic ester, a primary alcohol, and isolated or unconjugated double bonds. 

The basic carbohydrate molecule possesses an aldehyde or ketone group and a hydroxyl group on every carbon atom except the one involved in the carbonyl group. As a result, carbohydrates are defined as aldehyde or ketone derivatives of polyhydroxy alcohols and their reaction products. A look at the formula for glucose shows that it contains hydrogen and oxygen atoms in the ratio in which they are found in water. The name carbohydrate... 

The compounds formed when a hydroxyl group (-OH) is substituted for a hydrogen are called alcohols. They have the general formula R-OH. The hydroxyl radical looks exactly like the hydroxide ion, but it is not an ion. Where the hydroxide ion fits the definition of a complex ion - a chemical combination of two or more atoms that have colleetively lost or (as in this case) gained one or more electrons - the... 

The three alkaloids concerned, morphine, codeine and thebaine, all behave as tertiary bases. Morphine contains two hydroxyl groups of which one is phenolic and the other a secondary alcohol group. On methylation of the phenolic hydroxyl codeine results. On oxidation, codeine is transformed into codeinone by conversion of the secondary alcohol group into a carbonyl group, and when thebaine is boiled with A-sulphuric acid for a few minutes, it is hydrolysed into codeinone and methyl sulphate, and in other ways thebaine has been shown to contain two methoxyl groups. That the relationship between the three alkaloids is close may be illustrated by the following slightly extended formula —... 

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