5. Propose an arrow-pushing mechanism for the reactions shown below. а. H2SO4 OH heat

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
Problem 18E
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5. Propose an arrow-pushing mechanism for the reactions shown below.
а.
H,SO4
OH
heat
b.
OH
H3O*
-OH
C.
1. xs PhMgBr
2. H3O*
OH
HO,
Ph
Ph
Transcribed Image Text:5. Propose an arrow-pushing mechanism for the reactions shown below. а. H,SO4 OH heat b. OH H3O* -OH C. 1. xs PhMgBr 2. H3O* OH HO, Ph Ph
Expert Solution
Step 1

 a) Reaction is a dehydration of alcohol in which the alcohols are converted to alkenes, the reaction intermediate is stable carbocation.

b) Reaction is a Pinacol-Pinacolone rearrangement in which the intermediate is a stable carbocation.

c) This reaction is a Grignard reagent reaction on a cyclic esters in which the ring gets open.

All the required mechanism for above reaction are given in a detailed manner in a attached image. 

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