a) Propose a mechanism for the decarboxylation of THCA under acidic conditions. Hint: first the "enol" automerizes to the ketone, then decarboxylation occurs. OH THCA OH H3O+ heat OH $5 THC

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THC (tetrahydrocannabinol) is the primary psychoactive component of cannabis. THC is produced from
THCA (tetrahydrocannabinolic acid) when THCA is heated (i.e. when cannabis leaves are smoked or cooked).
a) Propose a mechanism for the decarboxylation of THCA under acidic conditions. Hint: first the "enol"
tautomerizes to the ketone, then decarboxylation occurs.
OH
THCA
OH
H3O+
heat
OH
THC
b) Which part of the mechanism do you think occurs more readily: tautomerization to the ketone or
decarboxylation? Why?
Transcribed Image Text:THC (tetrahydrocannabinol) is the primary psychoactive component of cannabis. THC is produced from THCA (tetrahydrocannabinolic acid) when THCA is heated (i.e. when cannabis leaves are smoked or cooked). a) Propose a mechanism for the decarboxylation of THCA under acidic conditions. Hint: first the "enol" tautomerizes to the ketone, then decarboxylation occurs. OH THCA OH H3O+ heat OH THC b) Which part of the mechanism do you think occurs more readily: tautomerization to the ketone or decarboxylation? Why?
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