The reaction of 10 with ethylene glycol and p-toluenesulfonic acid (p-TSOH, shown) in boiling toluene gives 11: LOME OMe но он Me Toluene Me OH (TSOH) 10 11 Propose a reasonable mechanism for this transformation. Classify the cyclization steps according to Baldwin rules (for example, a "5-exo-dig" cyclization).

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The reaction of 10 with ethylene glycol and p-toluenesulfonic acid (p-TSOH, shown) in boiling
toluene gives 11:
COME
OMe
но
OH
Me
Toluene
Me
sO,H
OH
(TSOH)
10
11
Propose a reasonable mechanism for this transformation.
Classify the cyclization steps according to Baldwin rules (for example, a "5-exo-dig"
cyclization).
Hints:
a) Number the atoms
b) Flatten the structures/assess the starting
material/product relationship
c) Pay attention to conformation (but you
don't need to account for any specific
stereochemistry shown)
Transcribed Image Text:The reaction of 10 with ethylene glycol and p-toluenesulfonic acid (p-TSOH, shown) in boiling toluene gives 11: COME OMe но OH Me Toluene Me sO,H OH (TSOH) 10 11 Propose a reasonable mechanism for this transformation. Classify the cyclization steps according to Baldwin rules (for example, a "5-exo-dig" cyclization). Hints: a) Number the atoms b) Flatten the structures/assess the starting material/product relationship c) Pay attention to conformation (but you don't need to account for any specific stereochemistry shown)
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