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Sodium ethoxide, also referred to as sodium ethanolate, is the ionic, organic compound with the formula CH 3 CH 2 ONa, C 2 H 5 O Na, or NaOEt (Et = ethyl). It is a white solid, although impure samples appear yellow or brown. It dissolves in polar solvents such as ethanol. It is commonly used as a strong base. [2]
Alkoxide compounds are derivatives of alcohols where the hydrogen of the –OH group is replaced by a metal; [2] for example, the sodium salt of ethanol (CH 3 CH 2 OH) is sodium ethoxide, containing ethoxide anions CH 3 CH 2 O − and sodium cations Na +.
If an alkoxide such as sodium ethoxide is used as base, deprotonation takes place only to the extent of about 0.1% because acetone is a weaker acid than ethanol (pK a = 16). If, however, a more powerful base such as sodium hydride (NaH) or lithium diisopropylamide ( LDA ) is used, a carbonyl compound can be completely converted into its enolate ...
For this reason, the conjugate sodium alkoxide base of the alcohol formed (e.g. sodium ethoxide if ethanol is formed) is often used, since the alkoxide is regenerated. In mixed Claisen condensations, a non-nucleophilic base such as lithium diisopropylamide , or LDA, may be used, since only one compound is enolizable.
Ether synthesis by reaction of salicylaldehyde with chloroacetic acid and sodium hydroxide [1] The Williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol . This reaction was developed by Alexander Williamson in 1850. [2]
When a small, unhindered base – such as sodium hydroxide, sodium methoxide, or sodium ethoxide – is used for an E2 elimination, the Zaytsev product is typically favored over the least substituted alkene, known as the Hofmann product. For example, treating 2-Bromo-2-methyl butane with sodium ethoxide in ethanol produces the Zaytsev product ...
A classic case is sodium methoxide produced by the addition of sodium metal to methanol: [citation needed] 2 CH 3 OH + 2 Na → 2 CH 3 ONa + H 2. Other alkali metals can be used in place of sodium, and most alcohols can be used in place of methanol. Generally, the alcohol is used in excess and left to be used as a solvent in the reaction.
The second step is organic oxidation with sodium ethoxide in ethanol. Because of the basic conditions the initial product quininone interconverts with quinidinone via a common enol intermediate and mutarotation is observed. In the third step the ketone group is reduced with aluminum powder and sodium ethoxide in ethanol and quinine can be ...