The correct statement regarding nucleophilic substitution reaction in a chiral alkyl halide is: [2024]
Racemisation occurs in reaction and inversion occurs in reaction.
Racemisation occurs in reaction and retention occurs in reaction.
Retention occurs in reaction and inversion occurs in reaction.
Racemisation occurs in both and reactions.
(A)
In reaction, carbocation is formed as an intermediate. Carbocation is planar and nucleophile may attack from either side of the plane. This gives a pair of enantiomers as reaction products i.e. product is racemic mixture. Although amount of inversion product is more than that of retention product because nucleophile starts attacking from back side even before leaving group has completely left the carbon. So in there is partial racemization.
In , there is 100% inversion because nucleophile attacks from the side opposite to leaving group.
Given below are two statements:
Statement-I: High concentration of strong nucleophilic reagent with secondary alkyl halides which do not have bulky substituents will follow mechanism.
Statement-II: A secondary alkyl halide when treated with a large excess of ethanol follows mechanism.
In the light of the above statements, choose the most appropriate from the options given below: [2024]
Statement I is true but Statement II is false.
Statement I is false but Statement II is true.
Both Statement I and Statement II are false.
Both Statement I and Statement II are true.
(D)
Secondary alkyl halide follows both and paths parallelly. Out of and , which one is preferred path by secondary alkyl halide depends upon other conditions such as strength of nucleophile and nature of solvent. Strong nucleophiles such as alkoxides and polar aprotic solvents such as DMF and DMSO prefer to keep the reaction along pathway. Weak nucleophiles such as water, alcohols and acetic acid and polar protic solvents such as water and alcohols (these are solvents as well as nucleophiles), prefer to keep the reaction along pathway.
Given below are two statements:
Statement (I): reactions are 'stereospecific', indicating that they result in the formation of only one stereo-isomer as the product.
Statement (II): reactions generally result in formation of product as racemic mixtures.
In the light of the above statements, choose the correct answer from the options given below: [2024]
Both Statement I and Statement II are true
Statement I is false but Statement II is true
Both Statement I and Statement II are false
Statement I is true but Statement II is false
(A)
Stereospecific reactions are those reactions for which if stereochemistry of reactants is changed, then major product formed is changed. In reactions, inversion occurs, so different stereoisomers give different products. Hence reactions are stereospecific.
In reactions, carbocation is formed as intermediate. Carbocation is planar hence nucleophile can attack from either side of the planar carbocation. This results in racemic mixture in products.