For the following reaction SN 2 H H HO: HO H What happens if instead of hydrogens we have the following substituents: forward-CH₂CH3, backward -C6Hs and in the plane -CH3 Select a) The bromide will have an R configuration and the alcohol will have an R configuration. b) The bromide will have an S configuration and the alcohol will have an R configuration. d) The bromide will have an S configuration and the alcohol will have an S configuration. e) The bromide will have an R configuration and the alcohol will have an S configuration. f) They are not chiral compounds H

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For the following reaction SN
2
HO:
HO-C
H
H
What happens if instead of hydrogens we have the following substituents: forward -CH₂CH3, backward -C6H5 and in the
plane -CH3
Select
a) The bromide will have an R configuration and the alcohol will have an R configuration.
b) The bromide will have an S configuration and the alcohol will have an R configuration.
d) The bromide will have an S configuration and the alcohol will have an S configuration.
e) The bromide will have an R configuration and the alcohol will have an S configuration.
f) They are not chiral compounds
Reaction 24. Nucleophilic substitution reaction on sp³ hybridized carbons.
Nu
R-X
R-Nu
X = leaving group (for example: Cl, Br, I, Tos)
Nu = nucleophile (for example: HS HO, RO, CN, 1°, RNH₂, H₂O)
Mechanistic details
SN1 mechanism for tertiary substrates: the leaving group
departs in a unimolecular rate-limiting step, generating
the carbocation, which in the second step reacts with the
nucleophile; ion pairs may be involved and carbocation
rearrangements may compete
SN2 mechanism for primary substrates: the nucleophile
displaces the leaving group in one-step bimolecular back-
side attack leading to inversion of configuration on
stereogenic centers
secondary, allylic or benzylic substrates may react by
both mechanisms
competition with elimination reactions (E1 and E2) often
observed
Reagents and conditions
variety of conditions and solvents
usually polar and protic solvents
for SN1 reactions
usually polar aprotic solvents for
SN2 reactions
H
H
H
H
Transcribed Image Text:For the following reaction SN 2 HO: HO-C H H What happens if instead of hydrogens we have the following substituents: forward -CH₂CH3, backward -C6H5 and in the plane -CH3 Select a) The bromide will have an R configuration and the alcohol will have an R configuration. b) The bromide will have an S configuration and the alcohol will have an R configuration. d) The bromide will have an S configuration and the alcohol will have an S configuration. e) The bromide will have an R configuration and the alcohol will have an S configuration. f) They are not chiral compounds Reaction 24. Nucleophilic substitution reaction on sp³ hybridized carbons. Nu R-X R-Nu X = leaving group (for example: Cl, Br, I, Tos) Nu = nucleophile (for example: HS HO, RO, CN, 1°, RNH₂, H₂O) Mechanistic details SN1 mechanism for tertiary substrates: the leaving group departs in a unimolecular rate-limiting step, generating the carbocation, which in the second step reacts with the nucleophile; ion pairs may be involved and carbocation rearrangements may compete SN2 mechanism for primary substrates: the nucleophile displaces the leaving group in one-step bimolecular back- side attack leading to inversion of configuration on stereogenic centers secondary, allylic or benzylic substrates may react by both mechanisms competition with elimination reactions (E1 and E2) often observed Reagents and conditions variety of conditions and solvents usually polar and protic solvents for SN1 reactions usually polar aprotic solvents for SN2 reactions H H H H
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