Group Members: Kayla Back, Rajat Goyal, and Kevin Sidoran

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Problem: Predict the mechanism for the following problem (caryophyllene molecule in acidic conditions
(H3O+) to produce the products caryolanol and clovene.

Mechanism for caryophyllene to caryolanol in acidic conditions (H3O+)

Steps of mechanism explained.

1. Alkene serves as nucleophile in caryophyllene. The more substituted (the trisubstituted one) alkene attacks the H3O+ molecule
yielding in a hydrogen addition to the less substituted carbon and a carbocation at the 3 position.
2. There is an intramolecular attack of the electrons from the other alkene (the disubstituted one) to the electrophilic carbocation
which makes a bridgehead. Attack can be from the back side or the front side. Attack is shown from the front side in this
mechanism. The carbocation shifts to where it is indicated in line 2 of the mechanism (still a 3 carbocation equally as stable).
Mec (H2O) functions as a nucleophile and attacks at the most electrophilic site (where the carbocation is located) and a
3. Water
product with a protonated OH (H2O+)functional group is formed.
4. Water serves as a base to deprotonate the H2O+ to an alcohol (OH) yielding the final product (caryolanol). Enantiomer of this
product is also formed (not shown)

Mechanism for caryophllene to clovene in acidic conditions (H3O+)

Steps of mechanism explained.

1. Alkene serves as nucleophile in caryophyllene. The more substituted alkene (the trisubstituted one) attacks the H3O+ molecule
yielding in a hydrogen addition to the less substituted carbon and a carbocation at the 3 position.
2. There is an intramolecular attack of the electrons from the other alkene (the disubstituted one) to the electrophilic carbocation which
makes a bridgehead. Attack can be from the back side or the front side. Attack is shown from the back side in this mechanism. The
carbocation shifts to where it is indicated in line 2 of the mechanism (still a 3 carbocation equally as stable).
3. There is a ring expansion as shown. This ring expansion yields a 2 carbocation from a 3 carbocation; however, due to ring strain of
the four membered ring being removed by ring expansion, this is an energetically favorable step.
4. Water serves as a base and elimination occurs. The enantiomer of the product is also formed (not shown)