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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.
It is a colourless gas that reacts with oxygen to give water and iodine. Although it is useful in iodination reactions in the laboratory, it does not have large-scale industrial uses, unlike the other hydrogen halides. Commercially, it is usually made by reacting iodine with hydrogen sulfide or hydrazine: [4] 2 I 2 + N 2 H 4 4 HI + N 2
The international pictogram for oxidizing chemicals. Dangerous goods label for oxidizing agents. An oxidizing agent (also known as an oxidant, oxidizer, electron recipient, or electron acceptor) is a substance in a redox chemical reaction that gains or "accepts"/"receives" an electron from a reducing agent (called the reductant, reducer, or electron donor).
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 carbocations, which are commercial dyes. [39]
These iodine compounds are hypervalent because the iodine atom formally contains in its valence shell more than the 8 electrons required for the octet rule. Hypervalent iodine oxyanions are known for oxidation states +1, +3, +5, and +7; organic analogues of these moieties are known for each oxidation state except +7.
The mechanism of carbonyl oxidation by iodine(III) reagents varies as a function of substrate structure and reaction conditions, but some generalizations are possible. Under basic conditions, the active iodinating species are iodine(III) compounds in which any relatively acidic ligands on iodine (such as acetate) have been replaced by alkoxide. [1]
This reaction, which is conducted on large scale industrially, requires the removal of the water from the reaction mixture as it is formed. Esters react in the presence of an acid or base to give back the alcohol and a salt. This reaction is known as saponification because it is used in the preparation of soap. Ethanol can also form esters with ...
A variety of agents are available commercially, many are derivatives of 1,3,5-triiodobenzene and contain about 50% by weight iodine. For most applications, the agent must be highly soluble in water and, of course, non-toxic and readily excreted. A representative reagent is Ioversol (Figure to right), [8] which has water-solubilizing diol ...