12. When 1-chloronaphthalene is treated with sodium amide, Na+NH2 , in the presence of piperidine, there is obtained not only I but also II, CI 1-chloronaphthalene piperidine in the ratio of 1:2. Similar treatment of 1-bromo- or 1-iodonaphthalene yields the same products and in the same 1:2 ratio. Show all steps in a mechanism that accounts for these observations. Can you suggest possible factors that might tend to favor Il over I.

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12.
When 1-chloronaphthalene is treated with sodium amide, Na+NH2 ,
in the presence of
piperidine, there is obtained not only I but also II,
CI
1-chloronaphthalene
piperidine
in the ratio of 1:2. Similar treatment of 1-bromo- or 1-iodonaphthalene
yields the same products and in the same 1:2 ratio. Show all steps in a
mechanism that accounts for these observations. Can you suggest
possible factors that might tend to favor Il over I.
Transcribed Image Text:12. When 1-chloronaphthalene is treated with sodium amide, Na+NH2 , in the presence of piperidine, there is obtained not only I but also II, CI 1-chloronaphthalene piperidine in the ratio of 1:2. Similar treatment of 1-bromo- or 1-iodonaphthalene yields the same products and in the same 1:2 ratio. Show all steps in a mechanism that accounts for these observations. Can you suggest possible factors that might tend to favor Il over I.
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