Alcohols. Alcohols are saturated hydrocarbons in which one or more of the hydrogen atoms are replaced by OH group.

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Presentation transcript:

Alcohols

Alcohols are saturated hydrocarbons in which one or more of the hydrogen atoms are replaced by OH group.

Alcohols they are divided into : a- Monohydric alcohols: which contain one OH group per molecule. b- Dihydric alcohols : which contain two OH groups per molecule c- Polyhydric alcohols : which contain three OH groups per molecule.

Alcohols

According to the position of the OH group in the molecule; monohydric alcohols are subdivided into three classes : Primary alcohols: in which the OH group is attached to the primary carbon atom. Secondary alcohols: in which the OH group is attached to the secondary carbon atom. Tertiary alcohols: in which the - OH group is attached to the tertiary carbon atom.

Alcohols Preparation: 1. Hydrolysis of the corresponding alkyl halide with aqueous alkali.

Alcohols 2- Hydrolysis of esters:

Alcohols 3- Hydrolysis of ethers in presence of dil H 2 SO 4.

Alcohols 4- Reduction of carbonyl compounds (aldehyde & ketone)

Alcohols Reduction is usually carried out by aluminum lithium hydride. Aldehyde on reduction gives the corresponding primary alc. while ketones give the corresponding secondary alcohols.

Alcohols 5- Action of Grignard reagent on carbonyl compounds:

Alcohols 5- Action of Grignard reagent on carbonyl compounds:

Alcohols 5- Action of Grignard reagent on carbonyl compounds:

Alcohols 6- By hydrogenation of CO at high P and T ( °C) in the presence of zinc chromite as a catalyst (ZnO & Cr 2 O 3 )

Alcohols 7- Ethyl alcohol can be obtained on an industrial scale by the fermentation of sugars.

Alcohols Physical properties: Alcohols are neutral, lower members are liquids and the higher are solids. The lower members are less volatile than to be expected from their molecular weight this is due to the hydrogen bonding extending over a chain of molecules, thus giving rise to a large molecule its volatility would be expected to be low.

Alcohols The lower alcohols are very soluble in water, and the solubility decreases as the molecular weight increases. Their solubility in water is to be expected, since the oxygen atom of the hydroxyl group in alcohols can form hydrogen bonds with the water molecules.

Alcohols In the lower alcohols the hydroxyl group constitutes a large part of the molecule, where as the molecular weight of the alcohol increases the hydrocarbon character of the molecule and hence the solubility in water decreases.

Alcohols Chemical Reactions: 1- Esterfication:

Alcohols Chemical Reactions: 2- Halogenation:

Alcohols Chemical Reactions: 3- Substitution reaction:

Alcohols Chemical Reactions: 4- Dehydration of alcohols:

Alcohols Chemical Reactions: 4- Dehydration of alcohols: This is earned in presence of dehydrating agent such as P 2 O 5 or conc. H 2 SO 4 or Al 2 O 3, the product is always an olefin. When 2-butyl alcohol is dehydrated, 2-butene is obtained. Here, dehydration like dehydrohalogenation follows Saytzeff’s rule.

Alcohols Chemical Reactions: 5- Oxidation of alcohols Dehydrogenation: Primary alcohols:

Alcohols Chemical Reactions: 5- Oxidation of alcohols Dehydrogenation: Secondary alcohols:

Alcohols Chemical Reactions: 5- Oxidation of alcohols Dehydrogenation: Tertiary alcohols:

Alcohols Chemical Reactions: Since the carbon atom of the carbinol group does not carry any hydrogen atoms, tertiary alcohols are not oxidized in neutral or alkaline medium. However, in acidic medium it is first dehydrated to an alkene which is then oxidized to a ketone (with a fewer number of carbon atoms).

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