OH CH3OH HⓇ OCH 3 In the space provided below please show a detailed, stepwise mechanism for the transformation shown above. You must show all intermediates (including proton transfer

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter8: Addition Via Carbocation
Section: Chapter Questions
Problem 16E: A student proposes the following reaction mechanism for the reaction in Model 6. Which step inthis...
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OH
CH3OH
HⓇ
OCH 3
In the space provided below please show a detailed, stepwise mechanism for the
transformation shown above. You must show all intermediates (including proton transfer
Transcribed Image Text:OH CH3OH HⓇ OCH 3 In the space provided below please show a detailed, stepwise mechanism for the transformation shown above. You must show all intermediates (including proton transfer
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I can see that it's correct to have a hydride shift from a secondary carbocation to another secondary carbocation in this case. I guess what I'm saying is, doesn't hydride shifts only occur when it only produces a more stable carbocation? For instance, secondary carbocation does a hydride shift to a tertiary carbocation. Is it correct to do a hydride shift from a secondary carbocation to another secondary carbocation in this case because the pi bond shifts to produce a tertiary carbocation? And this shift (from a secondary carbocation to another secondary carbocation) only plausible if the pi bond shifts afterwards to create the tertiary carbocation? 

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