Alcohols, Ethers, and Amines

The position of the hydroxyl group along the alkane chain is indicated by means of a number and a hyphen at the beginning of the name. If there is more than one hydroxyl group, prefixes such as di- and tri- are placed just before the -ol in the name, and the -e is not dropped from the alkane name. 

The alkane chain has five carbon atoms and is therefore a pentane chain. Drop the final -e and add -ol. Counting from the right end, so as to give the hydroxyl position the lowest possible number, the hydroxyl group is on the second carbon. Thus, the prefix 2- is used. The name of the alcohol is 2-pentanol. 

Solving Problems A Chemistry Handbook Chemistry Matter and Change 235 

Draw structures for the alcohols that have the following names, a. 2-butanol b. 1,2-butanediol c. 2-methyl-1-butanol 

Classify each compound as an ether or an amine, and name the compound. 

I Identify the functional groups that characterize alcohols, ethers, and amines. 

Oxygen and nitrogen are two of the most-common atoms found in organic functional groups. 

Real-World Reading Link The last time you had a vaccination, the nurse probably disinfected your skin with an alcohol wipe before giving you the injection. Did you know that the nurse was using a substituted hydrocarbon  

General Formula Simple Alcohol and Simple Hydrocarbon  

In Section 23.1, you learned that hydrogen atoms bonded to carhon atoms in hydrocarbons can be replaced by halogen atoms. Many other kinds of atoms or groups of atoms also can bond to carbon in the place of hydrogen atoms. In addition to structural variations, replacement of hydrogen by other elements is a reason that such a wide variety of organic compounds is possible. 

Models of an ethanol molecule and a water molecule are shown in the following diagram. 

As you compare the models, you can see that the covalent bonds from oxygen are at approximately the same angle as they are in water. Therefore, the hydroxyl groups of alcohol molecules are moderately polar, as with water, and are able to form hydrogen bonds with the hydroxyl groups of other alcohol molecules. As a result, alcohols have much higher boiling points than 

Ethanol is an effective antiseptic used to sterilize skin before an injection. It also is found in antiseptic hand cleaners. 

Because it evaporates more slowly than smaller alcohol molecules, 2-butanol is used as a solvent in some stains and varnishes. Draw the structures of two other alcohols that have the same molecular formula as 2-butanol, C4H10O. 

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AFM and STM in Photochemistry Including Photon Tunneling (Kaupp) Alcohols, Ethers, and Amines, Photolysis of Saturated (von Sonntag and... 

In Table XXV, the rates and amounts of absorption of various molecules are summarized (235). Polar molecules such as alcohol, ether, and amine are readily absorbed. In contrast, nonpolar molecules like hydrocarbons are sorbed only on the surface. The initial rates of absorption of molecules are plotted against the molecular size in Fig. 37. The initial rates of alcohol sorption greatly decrease as the molecular size increases from 20 A2 (methanol) to 35 A2 (1-butanol). The rates are higher for amines than for alcohols, regardless of the molecular size. This difference is due to the greater basicity of amines. Thus, it may be stated that the rate is primarily determined by the basicity (or polarity) and secondarily by the molecular size (235). 

The mobile phases used in normal-phase chromatography are based on nonpolar hydrocarbons, such as hexane, heptane, or octane, to which is added a small amount of a more polar solvent, such as 2-propanol.5 Solvent selectivity is controlled by the nature of the added solvent. Additives with large dipole moments, such as methylene chloride and 1,2-dichlor-oethane, interact preferentially with solutes that have large dipole moments, such as nitro- compounds, nitriles, amines, and sulfoxides. Good proton donors such as chloroform, m-cresol, and water interact preferentially with basic solutes such as amines and sulfoxides, whereas good proton acceptors such as alcohols, ethers, and amines tend to interact best with hydroxylated molecules such as acids and phenols. A variety of solvents used as mobile phases in normal-phase chromatography are listed in Table 2.2, some of which may need to be stabilized by addition of an antioxidant, such as 3-5% ethanol, because of the propensity for peroxide formation. 

Alcohols, ethers and certain amines also react and a broad series of compounds can be conveniently synthesized by the dimerization procedure. Typical examples are shown in Scheme 1, in which the new bond formed is marked in bold. For alcohols, ethers, and amines, highly selective attack at a C-H bond a to a heteroatom is observed. In cases where two different substances react, the two homo dimers and the hetero dimer are all formed. This can still be synthetically useful because the three compounds are often sufficiently different, either in polarity or volatility, to be readily separable by chromatography or fractional distillation. 

A. G. M. Barrett, Reduction of Carboxylic Acid Derivatives to Alcohols, Ethers and Amines, in Comprehensive Organic Synthesis (B. M. Trost, I. Fleming, Eds.), Vol. 8, 235, Pergamon Press, Oxford, U. K., 1991. 

The reactivity of an organic compound toward eaq depends on its functional groups because the main hydrocarbon chain is non-reactive. Aliphatic alcohols, ethers, and amines are also nonreactive (k 106 M 1 s-1), although alkylammonium ions show a slight reactivity and can transfer a proton to the hydrated electron. Isolated double bonds are practically nonreactive, for ethylene k <2-5 X 106 M -1 s-1, but conjugated systems or double bonds with an electron withdrawing group attached to them are very reactive. For example, butadiene and acrylic acid react with practically diffusion controlled rates ( 10 0 M -1 s-1). 

SONNTAG CvON, SCHUCHMANN H-P (1977) Photolysis of Alcohols, Ethers, and Amines, in Pitts JN Jr, Hammond GS, Gollnick K (eds.) Advances in Photochemistry, John Wiley Sons, New York, Vol. 10 59-145. 

Boron trifluoride, a colorless gas, forms adducts with a wide variety of electron-pair donors including water, alcohols, ethers, and amines a well-known reagent is the BF3-OEt2 adduct. With water below 20°C it forms the hydrates BF3-H20 and BF3-2H20, which in the liquid state are partially dissociated, e.g., BF3-2H20 = BF3OH + H30+. In dilute solution, BF3 forms the tetrafluoroborate anion, whose acid solutions are known as fluoroboric acid ... 

The solvomercuration of alkenes has an important synthetic valne since it allows the asymmetric functionalization of olefins. Although a large number of organomercurials have been isolated from these reactions, more commonly, they are reduced with alkaline NaBELi to yield the corresponding metal-free organic species (see Section 4.1). In this way, olefins can be converted into a wide range of organic species such as alcohols, ethers, and amines. 

P-acetylenic alcohols, ethers and amines but also with alkylacetylenes. With suitable reagents ring syntheses become possible, e.g. equation (198) -... 

Reduction of Carboxylic Acid Derivatives to Alcohols, Ethers and Amines... 

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