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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.
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. CH 3 CH 2 OH + H 2 SO 4 → CH 3 CH 2 OSO 3 H + H 2 O
Hydroboration–oxidation reaction is a two-step hydration reaction that converts an alkene into an alcohol. [1] The process results in the syn addition of a hydrogen and a hydroxyl group where the double bond had been. Hydroboration–oxidation is an anti-Markovnikov reaction, with
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 reaction is reversible and the formation of the sulfur trioxide is exothermic. 2 SO 2 + O 2 ⇌ 2 SO 3. The sulfur trioxide is absorbed into 97–98% H 2 SO 4 to form oleum (H 2 S 2 O 7), also known as fuming sulfuric acid or pyrosulphuric acid. The oleum is then diluted with water to form concentrated sulfuric acid. H 2 SO 4 + SO 3 → H ...
This reaction is important in the history of organic chemistry because it helped prove the structure of ethers. The general reaction mechanism is as follows: [3] An example is the reaction of sodium ethoxide with chloroethane to form diethyl ether and sodium chloride: C 2 H 5 Cl + C 2 H 5 ONa → C 2 H 5 OC 2 H 5 + NaCl
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.
In reactions of chiral, non-racemic epoxides, the configuration of the allylic alcohol product matches that of the epoxide substrate at the carbon whose C–O bond does not break (the starred carbon below). Besides β-elimination some other reactions [2] [3] are possible, as metalation of the epoxide ring can take place competitively.