Treatment of 4-pentenoic acid (margin) with B r 2 in the presence of dilute aqueous base yields

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Treatment of 4-pentenoic acid (margin) with Br2 in the presence of dilute aqueous base yields a nonacidic compound with the formula C5H7BrO2

(a) Suggest a structure for this compound and a mechanism for its formation. 

(b) Can you find a second, isomeric product whose formation is also mechanistically reasonable? 

(c) Discuss the issues that contribute to determining which of the two is the major product in this reaction. 

HO. 4-Pentenoic acid

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Organic Chemistry structure and function

ISBN: 978-1429204941

6th edition

Authors: K. Peter C. Vollhardt, Neil E. Schore

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