During a recent synthesis of hispidospermidin, a fungal isolate and an inhibitor of phospholipase C, the investigators employed employed a novel Friedel-Crafts acylation on a nonaromatic system (J. Am. Chem. Soc. 1998, 120, 4039-4040). The following acid chloride was treated with a Lewis acid, affording a mixture of two products, 1 and 2. Propose a plausible mechanism for the formation of compounds 1 and 2. H ☆ Part 1 H₂C AICI COCI H da Incorrect. Which of the four mechanistic steps is happening? Add curved arrow(s) to draw the first step of the mechanism. Modify the given drawing of the products as needed to show the intermediate that is formed in this step. Use the +/- tools to add/remove charges. CH₂ H :C: 2 Edit Drawing H₂C H CH₂ CI C N C M

During a recent synthesis of hispidospermidin, a fungal isolate and an inhibitor of phospholipase C, the investigators employed employed a novel Friedel-Crafts acylation on a nonaromatic system (J. Am. Chem. Soc. 1998, 120, 4039-4040). The following acid chloride was treated with a Lewis acid, affording a mixture of two products, 1 and 2. Propose a plausible mechanism for the formation of compounds 1 and 2. H ☆ Part 1 H₂C AICI COCI H da Incorrect. Which of the four mechanistic steps is happening? Add curved arrow(s) to draw the first step of the mechanism. Modify the given drawing of the products as needed to show the intermediate that is formed in this step. Use the +/- tools to add/remove charges. CH₂ H :C: 2 Edit Drawing H₂C H CH₂ CI C N C M

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter7: Alkynes

Section: Chapter Questions

Problem 7.19P

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Question

During a recent synthesis of hispidospermidin, a fungal isolate and an inhibitor of phospholipase C, the investigators employed
employed a novel Friedel-Crafts acylation on a nonaromatic system (J. Am. Chem. Soc. 1998, 120, 4039-4040). The following
acid chloride was treated with a Lewis acid, affording a mixture of two products, 1 and 2. Propose a plausible mechanism for
the formation of compounds 1 and 2.
CI
AICI
进一步农
COCI
2
Part 1
Incorrect. Which of the four mechanistic steps is happening?
Add curved arrow(s) to draw the first step of the mechanism. Modify the given drawing of the products as needed to show
the intermediate that is formed in this step. Use the +/- tools to add/remove charges.
CH₂
H
St
Edit Drawing
H₂C
H
CH₂
CI
Q
M
ΟΣ

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