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Acetone (2-propanone or dimethyl ketone) is an organic compound with the formula (CH 3) 2 CO. [22] It is the simplest and smallest ketone (>C=O).It is a colorless, highly volatile, and flammable liquid with a characteristic pungent odour, very reminiscent of the smell of pear drops.
The keto and enol tautomers of acetylacetone coexist in solution. The enol form has C 2v symmetry, meaning the hydrogen atom is shared equally between the two oxygen atoms. [4] In the gas phase, the equilibrium constant, K keto→enol, is 11.7, favoring the enol form.
The concerted mechanism of this step is similar to the mechanisms of the Baeyer–Villiger oxidation [6] and Criegee rearrangement reactions, and also the oxidation step of the hydroboration–oxidation process. [7] In 2009, an acidified bentonite clay was proven to be a more economical catalyst than sulfuric acid as the acid medium.
Acetoacetic ester synthesis is a chemical reaction where ethyl acetoacetate is alkylated at the α-carbon to both carbonyl groups and then converted into a ketone, or more specifically an α-substituted acetone. This is very similar to malonic ester synthesis. Acetoacetic ester synthesis equation
Vapor pressure of acetone based on formula, = + from Lange's Handbook of Chemistry, 10th ed. vapor pressure of acetone (log scale) based on formula, log 10 P m m H g = 7.02447 − 1161.0 224 + T {\displaystyle \scriptstyle \log _{10}P_{mmHg}=7.02447-{\frac {1161.0}{224+T}}} from Lange's Handbook of Chemistry , 10th ed.
The original reaction was a mixture of the reagents phenol, chloroform, and acetone in the presence of a sodium hydroxide solution. [2] Prior to Bargellini's research, the product attributed to this multi-component reaction (MCR) had been described as a phenol derivative in chemistry texts at the time.
The rearrangement of acetone oxime in the Beckmann solution involved three acetic acid molecules and one proton (present as an oxonium ion). In the transition state leading to the iminium ion (σ-complex), the methyl group migrates to the nitrogen atom in a concerted reaction as the hydroxyl group is expelled.
The reaction of acetone and iodine produces iodoacetone. The reaction is typically acid catalysed and first order with respect to acetone and the acid catalyst: [ 3 ] [ 6 ] C 3 H 6 O + I 2 → HI + C 3 H 5 IO