Draw the mechanism of the following reaction, using the curved-arrow notation to indicate the reorganization of electron density. Denote all intermediates, lone pairs, nonzero formal charges, countercharges, and reversibility or nonreversibility. Finally, explain concisely why a mixture of the stereoisomers 2 and 3 is obtained. 2H-Br: .. `CH3 `CH3 :OH + `CH3 :Br: 3 + + H-OH, :Br:

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
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Draw the mechanism of the following reaction, using the curved-arrow notation to indicate the
reorganization of electron density. Denote all intermediates, lone pairs, nonzero formal charges,
countercharges, and reversibility or nonreversibility. Finally, explain concisely why a mixture of
the stereoisomers 2 and 3 is obtained.
2 H-Br:
`CH3
`CH3
:OH
:Br:
+
`CH3
:Br:
..
3
+
+ H-OH, :Br:
Transcribed Image Text:Draw the mechanism of the following reaction, using the curved-arrow notation to indicate the reorganization of electron density. Denote all intermediates, lone pairs, nonzero formal charges, countercharges, and reversibility or nonreversibility. Finally, explain concisely why a mixture of the stereoisomers 2 and 3 is obtained. 2 H-Br: `CH3 `CH3 :OH :Br: + `CH3 :Br: .. 3 + + H-OH, :Br:
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