Compound 1 is observed to undergo debromination upon
Chapter 8, Problem 8.9(choose chapter or problem)
Compound 1 is observed to undergo debromination upon treatment with DMF to afford an alkene. The E isomer (compound 2) is obtained exclusively (none of the Z isomer is observed). A concerted mechanism (shown below) has been refuted by the observation that diastereomers of 1 also afford the E isomer exclusively when treated with DMF (J. Org. Chem. 1991, 56, 25822584): Br H Br H 1 H O N 2 (DMF) (a) Explain why the mechanism shown is inconsistent with this observation. (b) Classify this reaction as stereoselective or stereospecific and explain your choice.
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