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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.
Although nearly 100% sulfuric acid solutions can be made, the subsequent loss of SO 3 at the boiling point brings the concentration to 98.3% acid. The 98.3% grade, which is more stable in storage, is the usual form of what is described as "concentrated sulfuric acid".
In acid catalysis and base catalysis, a chemical reaction is catalyzed by an acid or a base. By Brønsted–Lowry acid–base theory, the acid is the proton (hydrogen ion, H +) donor and the base is the proton acceptor. Typical reactions catalyzed by proton transfer are esterifications and aldol reactions.
The reaction usually requires a catalyst, such as concentrated sulfuric acid: R−OH + R'−CO 2 H → R'−CO 2 R + H 2 O. Other types of ester are prepared in a similar manner−for example, tosyl (tosylate) esters are made by reaction of the alcohol with 4-toluenesulfonyl chloride in pyridine.
A typical mixture is 3 parts of concentrated sulfuric acid and 1 part of 30 wt. % hydrogen peroxide solution; [1] other protocols may use a 4:1 or even 7:1 mixture. A closely related mixture, sometimes called "base piranha", is a 5:1:1 mixture of water, ammonia solution ( NH 4 OH , or NH 3 (aq) ), and 30% hydrogen peroxide.
With concentrated sulfuric acid, granulated table sugar performs a degradation reaction which changes its form to a black solid-liquid mixture. [1] The carbon snake experiment can sometimes be misidentified as the black snake , "sugar snake", or "burning sugar" reaction, all of which involve baking soda rather than sulfuric acid.
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 ...
This equation shows that the pH of a solution of a weak acid depends on both its value and its concentration. Typical examples of weak acids include acetic acid and phosphorous acid . An acid such as oxalic acid ( HOOC − COOH {\displaystyle {\ce {HOOC-COOH}}} ) is said to be dibasic because it can lose two protons and react with two molecules ...