The cis and trans stereoisomers of 4-chlorocyclohexanol give different products when they react with OH ,

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The cis and trans stereoisomers of 4-chlorocyclohexanol give different products when they react with OH, as shown in the reactions given in Fig. P9.83.HO- Cl + OH trans-4-chlorocyclohexanol HO Cl + TOH cis-4-chlorocyclohexanol Figure P9.83 HO HO- A A + HO 11 B

(a) Give a curved-arrow mechanism for the formation of each product.

(b) Explain why the bicyclic material B is observed in the reaction of the trans isomer, but not in the reaction of the cis isomer.

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Organic Chemistry

ISBN: 9781936221349

6th Edition

Authors: Marc Loudon, Jim Parise

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