When 2-methyl-1,3-butadiene (isoprene) undergoes a 1,4-addition of hydrogen chloride, the major product that is formed is 1-chloro-3-methyl-2-butene.

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When 2-methyl-1,3-butadiene (isoprene) undergoes a 1,4-addition of hydrogen chloride, the major product that is formed is 1-chloro-3-methyl-2-butene. Little or no 1-chloro-2-methyl-2-butene is formed. How can you explain this?

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Organic Chemistry

ISBN: 978-1118133576

11th edition

Authors: Graham Solomons, Craig Fryhle, Scott Snyder

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Question Posted: Apr 19, 2016 09:07 AM

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When 2-methyl-1,3-butadiene (isoprene) undergoes a 1,4-addition of hydrogen chloride, the major product that is formed is 1-chloro-3-methyl-2-butene.

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The resonance hybrid I has the positive charge in pa...View the full answer

Organic Chemistry

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