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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.
For oxidations to the aldehydes and ketones, two equivalents of chromic acid oxidize three equivalents of the alcohol: 2 HCrO 4 − + 3 RR'C(OH)H + 8 H + + 4 H 2 O → 2 [Cr(H 2 O) 6] 3+ + 3 RR'CO. For oxidation of primary alcohols to carboxylic acids, 4 equivalents of chromic acid oxidize 3 equivalents of the alcohol. The aldehyde is an ...
Oppenauer oxidation, named after Rupert Viktor Oppenauer , [1] is a gentle method for selectively oxidizing secondary alcohols to ketones. Oppenauer oxidation reaction scheme. The reaction is the opposite Meerwein–Ponndorf–Verley reduction. [2] The alcohol is oxidized with aluminium isopropoxide in excess acetone.
Dimethyl sulfide (Me 2 S) is treated with N-chlorosuccinimide (NCS), resulting in formation of an "active DMSO" species that is used for the activation of the alcohol. Addition of triethylamine to the activated alcohol leads to its oxidation to aldehyde or ketone and generation of dimethyl sulfide. In variance with other alcohol oxidation using ...
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 ...
A Robinson annulation involves an α,β-unsaturated ketone and a carbonyl group, which first engage in a Michael reaction prior to the aldol condensation. [3] In the Guerbet reaction, an aldehyde, formed in situ from an alcohol, self-condenses to the dimerized alcohol.
2 C =O to propane-2,2-diol (H 3 C) 2 C(OH) 2 is about 10 −3, [1] while that of formaldehyde H 2 C =O to methanediol H 2 C(OH) 2 is 10 3. [2] For conversion of hexafluoroacetone (F 3 C) 2 C =O to the diol (F 3 C) 2 C(OH) 2, the constant is about 10 +6, due to the electron withdrawing effect of the trifluoromethyl groups. Similarly, the ...
The Wharton olefin synthesis or the Wharton reaction is a chemical reaction that involves the reduction of α,β-epoxy ketones using hydrazine to give allylic alcohols. [1] [2] [3] This reaction, introduced in 1961 by P. S. Wharton, is an extension of the Wolff–Kishner reduction.