Question 22Select correct and most relevant mechanism for each of the following reaction.Hint: Review Chapter 11.4.Brdilute HBrMechanism A:H.CH2Hprotontransfernucleophilic attackH ..OHCH2proton transferBr dilute H-Br:BrMechanism B:proton transfertertiarycarbocationhydrogen migration(rearrangement)HCH3dilute H-Br:Mechanism C:secondarycarbocation:Br:nucleophilic attackHHCH3Brtertiarycarbocation:Br:nucleophilicattacknucleophilicattackCH3dilute H-Br:Ηproton transfereliminationprimarycarbanionO:Br:H-Br:protondisassosiationproton transferBrBrdilute H-Br::Br::Br-HMechanism D:dilute H-Br:Bсsecondarycarbanionproton transferH.CH2CH2HH CH3H-Br:dilute H-Br:H-Br:proton transfer:Br:eliminationprotondisassosiationnucleophilic attacktertiarycarbocationHH CH3Br:Br:

Product of following reaction can be made by applying appropriate reaction mechanism.

Select correct and most relevant mechanism for each of the following reaction. Hint: Review Chapter 11.4. Br dilute HBr Mechanism A: H. CH2 nucleophilic attack HO HCH2 proton transfer H proton Br dilute H-Br: Br transfer Mechanism B: proton transfer dilute H-Br: tertiary carbocation hydrogen migration (rearrangement) HOCH3 H HCH3 = secondary carbocation Mechanism C: tertiary carbocation nucleophilic attack nucleophilic attack CH3 nucleophilic attack dilute H-Br: proton transfer primary carbanion Br: elimination H-Br: dilute H-Br: proton disassosiation Mechanism D: dilute H-Br: A B C proton transfer Br Br :Br-H secondary carbanion ..☺ CH2 proton transfer Н H CH3 H-Br: dilute H-Br: H-Br: proton transfer elimination proton disassosiation nucleophilic attack tertiary carbocation H HCH3 Br

Select correct and most relevant mechanism for each of the following reaction. Hint: Review Chapter 11.4. Br dilute HBr Mechanism A: H. CH2 nucleophilic attack HO HCH2 proton transfer H proton Br dilute H-Br: Br transfer Mechanism B: proton transfer dilute H-Br: tertiary carbocation hydrogen migration (rearrangement) HOCH3 H HCH3 = secondary carbocation Mechanism C: tertiary carbocation nucleophilic attack nucleophilic attack CH3 nucleophilic attack dilute H-Br: proton transfer primary carbanion Br: elimination H-Br: dilute H-Br: proton disassosiation Mechanism D: dilute H-Br: A B C proton transfer Br Br :Br-H secondary carbanion ..☺ CH2 proton transfer Н H CH3 H-Br: dilute H-Br: H-Br: proton transfer elimination proton disassosiation nucleophilic attack tertiary carbocation H HCH3 Br

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter9: Addition Via Cyclic Intermediate

Section: Chapter Questions

Problem 6CTQ

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Question 22 Select correct and most relevant mechanism for each of the following reaction. Hint: Review Chapter 11.4. dilute HBr Mechanism A: Mechanism B: 8 Br CH2 nucleophilic attack H..O HCH2 proton transfer H proton transfer Br dilute H-Br: Br proton transfer tertiary carbocation hydrogen migration (rearrangement) HCH3 H dilute H-Br: secondary carbocation nucleophilic attack H HCH3 tertiary carbocation Mechanism C: :Br: :O nucleophilic attack :Br CH3 nucleophilic dilute H-Br: :Br: attack = proton transfer elimination primary carbanion :Br: H-Br: dilute H-Br: proton disassosiation proton transfer Br :Br-H Mechanism D: dilute H-Br: A O B ос OD secondary carbanion Br proton transfer CH2 H CH3 H-Br: dilute H-Br: Η H-Br: proton transfer elimination proton disassosiation nucleophilic attack tertiary carbocation H H CH3 Θ Br: Br Br
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