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Orgo Lab experiment: Isomerization of Carvone 1. Carvone contains a ketone and two double bonds. However,...

Orgo Lab experiment: Isomerization of Carvone

1. Carvone contains a ketone and two double bonds. However, when treated with the concentrated acid only one reacts to create the carbocation. Which alkene reacts to form the carbocation and why only the one?

2. After the carbocation rearranges an elimination occurs, the alkene formed is a trisubstituted instead of the tetrasubstituted alternative. Why is this odd and what is the driving force for this specific alkene formation?

3. Using the H NMR and IR data given to explain how you can confirm the transformation of carvone into the product.

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Answer #1

Carvone structure is t . TOM in due to one double bond involving in rokonence with carbonyl carbon so only one double bond wi4 3 1 2 10041 Dom 153 cmo. proton) 121 (no, Proton) 130.9 (6.0 121 (6.6) 148 (mo. Proton) 4 S 8 23.6 (3.8) 9 23.9 (1.2) 10. 6

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