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Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters. The reaction mainly applies to primary and secondary alcohols. Secondary alcohols form ketones, while primary alcohols form aldehydes or carboxylic acids. [1] A variety of oxidants can be used.
The term alcohol originally referred to the primary alcohol ethanol (ethyl alcohol), which is used as a drug and is the main alcohol present in alcoholic drinks. The suffix -ol appears in the International Union of Pure and Applied Chemistry (IUPAC) chemical name of all substances where the hydroxyl group is the functional group with the ...
Primary alcohols do not react appreciably with Lucas reagent at room temperature. [3] Hence, the time taken for turbidity to appear is a measure of the reactivity of the class of alcohol, and this time difference is used to differentiate among the three classes of alcohols:
The order of reactivity follows that CH 2 > CH 3 > CH: Due to the rearrangement of the double bond, terminal olefins tend to give primary allylic alcohols: Cyclic alkenes prefer to undergo allylic oxidation within the ring, rather than the allylic position at the sidechain.
One workaround to avoid this method is to reduce the carboxylic acid derivative all the way down to an alcohol, then oxidize the alcohol back to an aldehyde. Other alternatives include forming a thioester or a Weinreb amide, then reducing the new species to an aldehyde through the Fukuyama reduction or Weinreb reaction respectively, or using ...
The order of addition of the reagents of the Mitsunobu reaction can be important. Typically, one dissolves the alcohol, the carboxylic acid, and triphenylphosphine in tetrahydrofuran or other suitable solvent (e.g. diethyl ether), cool to 0 °C using an ice-bath, slowly add the DEAD dissolved in THF, then stir at room temperature for several hours.
The order of reactivity, as shown by the vigour of the reaction with water or the speed at which the metal surface tarnishes in air, appears to be Cs > K > Na > Li > alkaline earth metals, i.e., alkali metals > alkaline earth metals, the same as the reverse order of the (gas-phase) ionization energies.
Other alkali metals can be used in place of sodium, and most alcohols can be used in place of methanol. Generally, the alcohol is used in excess and left to be used as a solvent in the reaction. Thus, an alcoholic solution of the alkali alkoxide is used. Another similar reaction occurs when an alcohol is reacted with a metal hydride such as NaH.