Depto. Química Orgánica

ALCOHOLS, PHENOLS AND ETHERS

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15/07/2017
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Alcohols
CH3OHCH3CH2OH(CH3)2CHOHOHCH2CH2OHOHCH2CH(OH)CH2OH
MethanolEthanolIsopropanolEthylenglycolGlycerin
It is called wood alcohol because it can be obtained by wood dry distillation.
It is used as solvent for paintings and as a combustible. It is HIGHLY POISONOUS and produces blindness when swallowed or breathed, even in low amounts. A 30 mL dosis is lethal. Metabolicaly, it is transformed into benzaldehyde and formic acid that prevent oxygen transport to blood.
It is obtained by fermentation of carbohydrates (sugars and starch) that is self-inhibited when alcohol content reaches ca. 15%. In order to raise alcohol content of bevarages, it is necessary to perform a distillation but the azeotropic 95:5 alcohol:water mixture cannot be surpassed.
Pure alcohol consumption is avoided by the addition of denaturalizing substances. Ethanol is VERY POISONOUS and kills a person when its blood level is above 0.4% . It is metabolyzed in the liver at a rate of 10 mL/h.
Nevertheless, it is used as an antidote against methanol or ethylenglycol poisoning.
It mixes with water and most organic solvents in all ratios. It is used as antifreezer, solvent, cleaner, dehydrating agent, extracting agent, synthesis intermediate and antiseptic. It is highly TOXIC by oral ingestion or inhalation.It was called glycol because Wurtz, who discovered it in 1855, felt a certain sweet flavor. It is used as solvent, antifreezer, hydraulic fluid, reaction intermediate in the synthesis of explosives, plasticizers, resins, fibers and artificial waxes. It is TOXIC by ingestion.

It was discovered by Scheele in 1779. Its name arises from its sweet flavor. It is a very viscous  substance, soluble in water and NON-TOXIC. The alkaline hydrolysis of triglicerides (fats) produces glycerine and soaps. The triple nitrate of glycerine is a powerful explosive.
Nomenclature of alcohols Nomenclature

Physical  and Bond Properties of alcohols Physical  and Bond Properties
Acid-Base Properties of alcohols Acid-Base Properties
Preparation of alcohols Preparation

Reactivity of alcohols Reactivity

Phenols
Runge
C6H5OH
Phenol

Phenol, formerly named carbolic acid, was discovered by Runge in 1834 from tar. It melts at 43ºC, boils at 183ºC and has a not too pleasant, characteristic smell. It is very soluble in water and in the majority of organic solvents. It is caustic and very poisonous. Just 1 g can kill an averege person. Phenol can poison by skin absorption. Its uncontrolled release as industrial waste can make a large damage to aquifers. It kills the aquatic fauna at a concentration as low as 1 ppm. In the presence of chlorine (used in water treatment) phenol can be transformed into chlorophenol of an foul taste. However, phenol can be easily and naturaly removed from the environment by pond rushes or reeds, very common aquatic plants.

Phenol nomenclature Nomenclature

Acid-base properties of phenols Acid-Base Properties
Preparation of Phenols Preparation

Reactivity of phenols Reactivity

Ethers
Ethers are in general low reactive species and many of them are thus used as solvents. Nevertheless some of them bear quite attractive structures and spectacular properties. They are named crown ethers discovered by Pedersen in 1967.
reconocimiento 12c4 Li
reconocimiento 15c5 Na
reconocimiento 18c6 K
The discovery of crown ethers and the study of their properties opened up the horizon to what has been called Supramolecular Chemistry and deserved to Pedersen and other two researchers, Lehn and Cram, the sharing of 87' Noble Prize in Chemistry.
Pedersen
Charles J. Pedersen (1940-1989 ): American chemist of Norwegian origin, linked to the research department of Du Pont where he made important discoveries related to ethyllead, hydrocarbon stabilization and, in the 60's, crown-ether chemistry. The latter research deserved him the 87' Nobel Prize in Chemistry together with D.J. Cram and J.-M. Lehn.
Lehn
Jean Marie Lehn (1939- ): French chemist, professor of the Louis Pasteur University at Strasbourg, carries out important research in the field of Organic Synthesis, especially related to the preparation and behavior of cyclic molecules ("hollow molecules") with structures similar to those of enzimes' active pockets. He shared with Cram and Pedersen the 87' Nobel Prize in Chemistry.
Cram
D.J. Cram (1919-2001): American chemist, professor of the University of California at Los Angeles. He widened Pedersen's work on crown-ethers and prepared 3D molecular architectures mimiking the way natural molecules work. He shared with Pedersen and Lehn the Nobel Prize of Chemistry in 1987.
Nomenclature of ethers Nomenclature

Physical and bond properties of ethers Physical and Bond Properties
Preparation of ethers Preparation

Reactivity of ethers Reactivity

Molecular recognition Molecular Recognition

Sulfur Compounds
The sulfur compounds anologous to alcohols and ethers are called thiols and thioethers (sulfides).
H2SCH3SHCH3SSCH3
Hydrogen sulfideMethylthiolDimethydisulfide
Nomenclature and properties of sulfur compounds Nomenclature and Properties
Reactivity of sulfur compounds Reactivity