Organic Chemistry (8th Edition)

Published by Pearson
ISBN 10: 0321768418
ISBN 13: 978-0-32176-841-4

Chapter 8 - Reactions of Alkenes - Problems: Problem 8-18 b

Answer

The mechanism would be addition of halogens. Since it is in non-polar solvent, two chlorines with attached across each the double bond.
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Work Step by Step

Since there are two double bonds and two moles of $Cl_2$, the reaction with happen at both the double bonds. The chlorines will be added trans. The mechanism would be: 1) Electrophilic attack forms a chloronium ion. 2) The chloride ion opens the chloronium ion. All stereoisomers will be produced considering that the chlorines attached to the double bond are always trans.
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