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Sodium hydride is the chemical compound with the empirical formula Na H.This alkali metal hydride is primarily used as a strong yet combustible base in organic synthesis.NaH is a saline (salt-like) hydride, composed of Na + and H − ions, in contrast to molecular hydrides such as borane, silane, germane, ammonia, and methane.
In equatorial attack (shown in blue), the hydride avoids the 1,3-diaxial interaction, but the substrate undergoes unfavorable torsional strain when the newly formed alcohol and added hydrogen atom eclipse each other in the reaction intermediate (as shown in the Newman projection for the axial alcohol).
Fig. 1 shows an example of a diastereoselective CBS reduction being used to prepare a complex macrocyclic alcohol en route to the synthesis of 11-desmethyllaulimalide [22] (an analog of the antitumor agent laulimalide). The authors noted that CBS reduction was much more effective than using either lithium tert-butoxyaluminum hydride or L ...
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.
In practice, considerable sodium is consumed by the formation of hydrogen. [citation needed] For this reason, an excess of sodium is often required. Because the hydrolysis of sodium is rapid, not to mention dangerous, the Bouveault-Blanc reaction requires anhydrous ethanol and can give low yields with insufficiently dry ethanol.
The k' pathway implicates a reaction between the doubly charged anion (RCHO 2 2−) and the aldehyde. The direct transfer of hydride ion is evident from the observation that the recovered alcohol does not contain any deuterium attached to the α-carbon when the reaction is performed in the presence of D 2 O.
The Wolff–Kishner reduction is a reaction used in organic chemistry to convert carbonyl functionalities into methylene groups. [1] [2] In the context of complex molecule synthesis, it is most frequently employed to remove a carbonyl group after it has served its synthetic purpose of activating an intermediate in a preceding step.
In organic chemistry, the oxy-Cope rearrangement is a chemical reaction.It involves reorganization of the skeleton of certain unsaturated alcohols. It is a variation of the Cope rearrangement in which 1,5-dien-3-ols are converted to unsaturated carbonyl compounds by a mechanism typical for such a [3,3]-sigmatropic rearrangement.