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  • Which of the following statements are correct about the mechanism of this reaction? (a) Acarbocation will be formed as an intermediate in the reaction.

Which of the following statements are correct about the mechanism of this reaction?

 

(i) A carbocation will be formed as an intermediate in the reaction.
(ii) OH^{-} will attach the substrate (b) from one side and Cl^{-} will leave it simultaneously from other side.
(iii) An unstable intermediate will be formed in which OH^{-} and Cl^{-} will be attached by weak bonds.
(iv) Reaction proceeds through S_N1 mechanism.

Answers (1)

(i), (iv) are correct. As the given reaction is a tertiary halide, therefore S_N1 mechanism will be present and as an intermediate, carbocation is formed.

The SN1 mechanism is a two-step process that describes a nucleophilic substitution reaction in organic chemistry:

  • Step 2

    The carbocation reacts with the nucleophile to form the substitution product.

  • Step 1

    The bond between the carbon atom and the leaving group breaks, forming a carbocation and an anionic leaving group.

Here are some key points about the SN1 mechanism:

  • Carbocation

    The carbocation is a positively charged carbon atom with three bonds. It is sp2 hybridized and has trigonal planar geometry. 

  • Nucleophile

    The nucleophile attacks the carbocation's empty p orbital, forming a new bond and returning the carbon to tetrahedral geometry. 

  • Rate-determining step

    The rate-determining step of the reaction is determined by the electrophilicity of the leaving group. 

  • Racemic mixture

    The nucleophile can attack the carbocation from either side, resulting in the formation of both enantiomers. This leads to a racemic mixture of both enantiomers. 

  • Deprotonation

    The product of the second step is often positively charged, and a third deprotonation step is usually required to form the neutral substitution product.

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