1. The Guam bubble snail (Haminoea cymbalum) contains kumepaloxane, a chemical signal agent discharged when this mollusk is disturbed by predatory carnivorous fish. The biosynthesis of kumepaloxane is thought to occur via an enzymatic equivalent of a "Br₂/ H₂O" - halohydrin formation. ICH 3 Br₂ Precursor? (R) .... (R) (S) (S) (E) HBr Kumepaloxane Br Draw the structure of the precursor to kumepaloxane which is an alkene alcohol. Write a detailed mechanism by which the alkene alcohol in part (a) is converted to kumepaloxane when Br2 (no light and no perxoxide) is added. What is the other stereoisomer of kumepaloxane that could be formed?

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1. The Guam bubble snail (Haminoea cymbalum) contains kumepaloxane, a chemical signal
agent discharged when this mollusk is disturbed by predatory carnivorous fish. The
biosynthesis of kumepaloxane is thought to occur via an enzymatic equivalent of a "Br₂/
H₂O" - halohydrin formation.
Br₂
(b)
(c)
Precursor?
(R)
(R)
(S)
(S)
||||| CH3
HBr
Kumepaloxane
Br
Draw the structure of the precursor to kumepaloxane which is an alkene alcohol.
Write a detailed mechanism by which the alkene alcohol in part (a) is converted to
kumepaloxane when Br₂ (no light and no perxoxide) is added.
What is the other stereoisomer of kumepaloxane that could be formed?
Transcribed Image Text:1. The Guam bubble snail (Haminoea cymbalum) contains kumepaloxane, a chemical signal agent discharged when this mollusk is disturbed by predatory carnivorous fish. The biosynthesis of kumepaloxane is thought to occur via an enzymatic equivalent of a "Br₂/ H₂O" - halohydrin formation. Br₂ (b) (c) Precursor? (R) (R) (S) (S) ||||| CH3 HBr Kumepaloxane Br Draw the structure of the precursor to kumepaloxane which is an alkene alcohol. Write a detailed mechanism by which the alkene alcohol in part (a) is converted to kumepaloxane when Br₂ (no light and no perxoxide) is added. What is the other stereoisomer of kumepaloxane that could be formed?
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