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

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

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter19: Eas: Electrophilic Aromatic Substitution

Section: Chapter Questions

Problem 45E

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