The cis and trans stereoisomers of 4-chlorocyclohexanol give different products when they react with OH ,
Question:
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.
(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.
Transcribed Image Text:
HO- Cl + OH trans-4-chlorocyclohexanol HO Cl + TOH cis-4-chlorocyclohexanol Figure P9.83 HO HO- A A + HO 11 B (alternate views) 0- a с OH
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a H Product A results from antielimination by a conventional E2 reaction HO H E FH HO 3cyclohexe...View the full answer
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