For the following reaction SN2HO:HO-CHHWhat happens if instead of hydrogens we have the following substituents: forward -CH₂CH3, backward -C6H5 and in theplane -CH3Selecta) 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 compoundsReaction 24. Nucleophilic substitution reaction on sp³ hybridized carbons.NuR-XR-NuX = leaving group (for example: Cl, Br, I, Tos)Nu = nucleophile (for example: HS HO, RO, CN, 1°, RNH₂, H₂O)Mechanistic detailsSN1 mechanism for tertiary substrates: the leaving groupdeparts in a unimolecular rate-limiting step, generatingthe carbocation, which in the second step reacts with thenucleophile; ion pairs may be involved and carbocationrearrangements may competeSN2 mechanism for primary substrates: the nucleophiledisplaces the leaving group in one-step bimolecular back-side attack leading to inversion of configuration onstereogenic centerssecondary, allylic or benzylic substrates may react byboth mechanismscompetition with elimination reactions (E1 and E2) oftenobservedReagents and conditionsvariety of conditions and solventsusually polar and protic solventsfor SN1 reactionsusually polar aprotic solvents forSN2 reactionsHHHH

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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

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

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter14: Elimination

Section: Chapter Questions

Problem 33E

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