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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 reaction stoichiometry implicates the Cr(IV) species "CrO 2 OH −", which comproportionates with the chromic acid to give a Cr(V) oxide, which also functions as an oxidant for the alcohol. [ 6 ] The oxidation of the aldehydes is proposed to proceed via the formation of hemiacetal -like intermediates, which arise from the addition of the O ...
If produced from oleochemical feedstock or the Ziegler process, the hydrocarbon chain of the alcohol will be linear. If derived using the oxo process, a low level of branching will appear usually with a methyl or ethyl group at the C-2 position, containing even and odd amounts of alkyl chains. [3] These alcohols react with chlorosulfuric acid:
Mercury compounds such as mercury sulfate and mercury(II) acetate are commonly used as catalysts in oxymercuration-demercuration, a type of electrophilic addition reaction which results in hydration of an unsaturated compound. The hydration of an alkene results in an alcohol that follows the regioselectivity predicted by Markovnikov's rule.
Ethyl sulfate can be produced in a laboratory setting by reacting ethanol with sulfuric acid under a gentle boil, while keeping the reaction below 140 °C. The sulfuric acid must be added dropwise or the reaction must be actively cooled because the reaction itself is highly exothermic.
Tertiary alcohols react with strong acids to generate carbocations. The reaction is related to their dehydration, e.g. isobutylene from tert-butyl alcohol. A special kind of dehydration reaction involves triphenylmethanol and especially its amine-substituted derivatives. When treated with acid, these alcohols lose water to give stable ...
The Williamson reaction is also frequently used to prepare an ether indirectly from two alcohols. One of the alcohols is first converted to a leaving group (usually tosylate), then the two are reacted together. The alkoxide (or aryloxide) may be primary and secondary. Tertiary alkoxides tend to give elimination reaction because of steric hindrance.
Dess–Martin periodinane (DMP) is a chemical reagent used in the Dess–Martin oxidation, oxidizing primary alcohols to aldehydes and secondary alcohols to ketones. [1] [2] This periodinane has several advantages over chromium- and DMSO-based oxidants that include milder conditions (room temperature, neutral pH), shorter reaction times, higher yields, simplified workups, high chemoselectivity ...