What is Corey House Reaction?
The coupling reaction is a good synthetic way to join two alkyl groups together to produce higher alkanes. This versatile method is known as the Corey-House reaction.
Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, sublimation reactions, pericyclic reactions, rearrangement reactions.
The Gilman reagent reacts with alkyl halide to give an alkane, which has a higher carbon number than the starting alkyl halide. The Corey-House reaction is useful and common in organic synthesis, but this reaction is limited to a 1o alkyl halide and the alkyl groups in the Gilman reagents may be 1o, 2o or 3o.
Alkyl halides react with lithium in dry ether to form alkyl lithium.
R-X + 2Li ⇾ R-Li + LiX
This alkyllithium reacts with CuI to give Dialkyl Lithium Cuprate known as Gilman reagent.
2R-Li + CuI ⇾ R2CuLi + LiI
This dialkyl lithium cuprate reacts with alkyl halide to give alkane and the reaction is known as Corey-House synthesis.
R2CuLi + R’-X ⇾ R-R’ + R-Cu + LiX
In this reaction R’-X may be methyl halide, p-alkyl halide or sec alkyl halide. The alkyl group of dialkyl lithium cuprate may be methyl, primary, secondary or tertiary.
In this reaction dialkyl lithium cuprate also reacts with aryl halide, alkyl halide and vinyl halide.
Importance of Corey-House Synthesis
This method is a better method than the Wurtz reaction. An alkyl halide and a lithium dialkyl copper are reacted to give a higher hydrocarbon.
R’-X + R3-CuLi ⇾ R-R’ + R-Cu + LiX
(R and R’ may be same or different)
CH3CH2CH2Br + (CH3)2CuLi ⇾ CH3CH2CH2CH3 + CH3Cu + LiBr
A notable feature of this reaction is that it can be used for preparing symmetrical, unsymmetrical, straight chain or branched chain alkanes.
For a better yield of the product, the alkyl halide used should be primary whereas lithium dialkyl copper may be primary, secondary or tertiary.
Frequently Asked Questions on Corey House Reaction
What do you mean by the Corey House reaction?
The Corey–House synthesis (also known as the Corey–Posner–Whitesides–House reaction and other permutations) is an organic reaction involving the reaction of a lithium divinylcuprate (R2CuLi) to form a new alkane with an organyl (pseudo) halide (RX) and an unknown organocopper compound.
How are alkanes prepared?
Alkane can be prepared by hydrogenation from the alkene and alkyne. Through this process, the present catalyst adds dihydrogen gas to the alkynes and alkenes. Such finely divided catalysts form alkanes like nickel, palladium, or platinum.
Why are Grignard reactions important?
The Grignard reaction is an organometallic chemical reaction in which alkyl, allyl, vinyl, or aryl-magnesium halides (Grignard reagent) in an aldehyde or ketone are added to a carbonyl ring. The reaction is critical for carbon – carbon bond formation.
What is Wurtz reaction in chemistry?
Wurtz reaction is an organic chemical coupling reaction in which sodium metal is reacted with two alkyl halides in the atmosphere given by a dry ether solution to form a higher alkane, along with a sodium and halogen compound.
How are alkynes prepared?
Larger alkynes can be produced by reacting with an acetylide ion, an alkyl halide that is formed from a shorter alkyne. Since the reactions to substitution and elimination proceed via the formation of a specific intermediate, these two forms of reactions often occur at the same time. Preparation of ethyne (acetylene)