a-Terpineol, a naturally occurring monoterpene alcohol,isomerizes to 1,8-cineole and 1,4-cineole when treatedwith acid. Draw a complete, detailed mechanism toaccount for the formation of each product.H,SO,HOa-Terpineol1,8-Cineole1,4-Cineole

In the reactant, there are two nucleophilic centers, one is the -OH group and another is alkene so…

Answered: a-Terpineol, a naturally occurring…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions

Section30.SE: Something Extra

Problem 27AP

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a-Terpineol, a naturally occurring monoterpene alcohol, isomerizes to 1,8-cineole and 1,4-cineole when treated with acid. Draw a complete, detailed mechanism to account for the formation of each product. H,SO, HO a-Terpineol 1,8-Cineole 1,4-Cineole