A chiral (R)-configuration alkyl halide of formula C7H15Cl reacts with H2O to give a product, formula C7H16O, as a racemic mixture.

Which of the following statements is true?

Question

A chiral (R)-configuration alkyl halide of formula C7H15Cl reacts with H2O to give a product, formula C7H16O, as a racemic mixture.

Which of the following statements is true?

BlackTom AI · Accepted Answer

Consider the type of substitution reaction that would convert an alkyl chloride into an alcohol in water. 
Option 1: The reaction proceeds via an SN1 mechanism, which involves a bimolecular transition-state species. This mixes two incorrect ideas: SN1 is not bimolecular in its rate-determining step; it proceeds via a unimolecular formation of a carbocation, followed by capture by solvent. Calling the transition state bimolecular here is inaccurate for SN1.
Option 2: The reaction proceeds via an SN2 mechanism, which involves a bimolecular transition-state species. While SN2 does involve a bimolecular transition state with simultaneous bond-breaking and bond-forming, SN2 on a chiral center would lead to inversion of configuration rather than racemization. Since the product is described as a racemic mixture, this mechanism alone cannot explain the outcome.
Option 3: The reaction proceeds via an SN1 mechanism, which involves a carbocation intermediate. This is consistent with a racemic product: after loss of Cl–, a planar carbocation is formed, and attack by water from either face yields both enantiomers, producing a racemate. Hence SN1 with a carbocation fits both the mechanism and the observed racemic outcome.
Option 4: The reaction proceeds via an SN2 mechanism, which involves a carbocation intermediate. SN2 reactions do not proceed through carbocation intermediates; they proceed via a concerted backside attack without discrete carbocation formation. Therefore mentioning a carbocation in SN2 is incorrect.
In summary, SN1 correctly accounts for the unimolecular rate-limiting step forming a planar carbocation and the subsequent non-stereospecific capture by water that yields a racemic mixture, while the other options contain misstatements about bimolecular transitions, the involvement of carbocations in SN2, or the fundamental mechanism.

CHEM 110 Lecture Quiz Week 7

A chiral (R)-configuration alkyl halide of formula C7H15Cl reacts with H2O to give a product, formula C7H16O, as a racemic mixture. Which of the following statements is true?

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