A test set of 264 nucleophilic substitution reactions was studied via accurate
quantum chemical reaction to establish the relative difference of SN1 versus SN2
mechanisms. In low polar solvents, reaction involving anionic nucleopbiles and
leaving groups favoured SN2 pathways. SNI was preferred for neutral
nucleophiles and leaving groups except where Cabocation intermediates are
exceptionally unstable. For neutral nucleophiles and anionic leaving groups SN2
is generally preferred over SN1 except for exceptionally stable Cabocation
intermediates.
In these questions, a statement of assertion followed by a statement of reason
I
is given. Choose the correct answer out of the following choices.
(a) Assertion and reason both are correct statements and reason is correct
explanation for assertion.
(b) Assertion and reason both are correct statement but reason is not correct
explanation for assertion.
(c) Assertion is correct statement but reason is wrong statement.
(d) Assertion is wrong statement but reason is correct statement.
(i) Assertion: benzoyl chloride undergoes SN1 mechanism.
Reason :Benzyl chloride is primary halide but forms a stable cabocation.
Answers
Answer:
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Answer:
A test set 264 nucleophilic substitution reactions was studied via accurate quantum chemical reactions to establish the relative preferences for SN1 versus SN2 mechanisms. In low polar solvents, reactions involving anionic nucleophiles and leaving groups favored SN2 pathways. In contrast, SN1 is preferred for those reactions involving neutral nucleophiles and leaving groups except where the carbocation intermediates are exceptionally unstable. For neutral nucleophiles and anionic leaving groups, SN2 is generally preferred over SN1 except for exceptionally stable carbocation intermediates. On the basis of these studies, candidate reactions for which distinct SN1 or SN2 preferences could be reversed by electric fields were selected. As proof of concept, the SN1/SN2 preferences for the reaction of tBu-triflate with pyridine (SN2 to SN1) and with piperidine (SN1 to SN2) were switched by both charged functional groups and point charges (i.e., electric fields) along the reaction axis, with a positive charge on the nucleophile side favoring SN1 and a negative charge favoring SN2 for these reactions.
Explanation:
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