Birch Reduction || Dissolving Metal Reduction || Concept Booster | Jee Mains | Advance | NEET

Hello Guys, In this video, we are going to discuss a very important topic for Jee Mains, advanced, NEET and AIIMS. The Birch reduction is an organic reaction where aromatic rings undergo a 1,4-reduction to provide unconjugated cyclohexadienes. The reduction is conducted by sodium or lithium metal in liquid ammonia and in the presence of an alcohol. The mechanism begins with a single electron transfer(SET) from the metal to the aromatic ring, forming a radical anion. The anion then picks up a proton from the alcohol which results in a neutral radical intermediate. Another SET, and abstraction of a proton from the alcohol results in the final cyclohexadiene product and two equivalents of metal alkoxide salt as a byproduct. In the case of substituted aromatic rings, the regiochemistry can be predicted using Birch's empirical rules.
Alkynes can be reduced to trans-alkenes with the use of sodium dissolved in an ammonia solvent. An Na radical donates an electron to one of the P bonds in a carbon-carbon triple bond. This forms an anion, which can be protonated by a hydrogen in an ammonia solvent. This prompts another Na radical to donate an electron to the second P orbital. Soon after this anion is also protonated by a hydrogen from the ammonia solvent, resulting in a trans-alkene.
R-C≡C-R + 2 Na in NH3 (liq) = trans R-CH=CH-R + 2 NaNH2
Many other important reactions from dissolving metal reaction has been discussed in details. We Hope this would be great help for you Guys.
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