Which statement(s) best describe(s) the stereochemical outcomes of SN1/SN2 react
ID: 475544 • Letter: W
Question
Which statement(s) best describe(s) the stereochemical outcomes of SN1/SN2 reactions, based on the allowed orbital interactions. Choose all statements below that is/are correct.
SN2 gives both retention and inversion of stereochemistry at the reacting center, since it is bimolecular ("2" in SN2)
SN2 gives both retention and inversion of stereochemistry at the reacting center, since approach of the nucleophile can either be on the same side or opposite side of the leaving group, based on HOMO/LUMO interactions
SN1 gives both retention and inversion of the stereochemistry at the reacting center, since the incoming nucleophile can interact with either lobe of the empty p orbital on the carbocation
SN1 gives racimization of a reactant that is chiral at the point of leaving group attachment
An optically active reactant that is chiral at the point of leaving group attachment will give an optically active product for an SN2 reaction
SN2 gives racimizaiton of a reactant that is chiral at the point of leaving group attachment
Because of orbital symmetry, SN1 gives a chiral product if the reactant is chiral at the point of leaving group attachment
Overlap of the nucleophile with the LUMO C-leaving group sigma* orbital requires the nucleophile to approach from the opposite face only.
a.SN2 gives both retention and inversion of stereochemistry at the reacting center, since it is bimolecular ("2" in SN2)
b.SN2 gives both retention and inversion of stereochemistry at the reacting center, since approach of the nucleophile can either be on the same side or opposite side of the leaving group, based on HOMO/LUMO interactions
c.SN1 gives both retention and inversion of the stereochemistry at the reacting center, since the incoming nucleophile can interact with either lobe of the empty p orbital on the carbocation
d.SN1 gives racimization of a reactant that is chiral at the point of leaving group attachment
e.An optically active reactant that is chiral at the point of leaving group attachment will give an optically active product for an SN2 reaction
f.SN2 gives racimizaiton of a reactant that is chiral at the point of leaving group attachment
g.Because of orbital symmetry, SN1 gives a chiral product if the reactant is chiral at the point of leaving group attachment
h.Overlap of the nucleophile with the LUMO C-leaving group sigma* orbital requires the nucleophile to approach from the opposite face only.
Explanation / Answer
SN1 gives both retention and inversion of the stereochemistry at the reacting center, since the incoming nucleophile can interact with either lobe of the empty p orbital on the carbocation
SN1 gives racimization of a reactant that is chiral at the point of leaving group attachment
An optically active reactant that is chiral at the point of leaving group attachment will give an optically active product for an SN2 reaction
Because of orbital symmetry, SN1 gives a chiral product if the reactant is chiral at the point of leaving group attachment
c.SN1 gives both retention and inversion of the stereochemistry at the reacting center, since the incoming nucleophile can interact with either lobe of the empty p orbital on the carbocation
d.SN1 gives racimization of a reactant that is chiral at the point of leaving group attachment
e.An optically active reactant that is chiral at the point of leaving group attachment will give an optically active product for an SN2 reaction
g.Because of orbital symmetry, SN1 gives a chiral product if the reactant is chiral at the point of leaving group attachment
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