why does Cl add ortho here?

[Kneecoal]

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In Destroyer Road map 1, cyclohexane with a double bonded O has Cl2/H3O+ added to it, and the Cl is added ortho to the =O -- what's special about it being in H3O+ that it adds ortho here instead of meta?

thanks for all the help!

 

[UCB05]

In Destroyer Road map 1, cyclohexane with a double bonded O has Cl2/H3O+ added to it, and the Cl is added ortho to the =O -- what's special about it being in H3O+ that it adds ortho here instead of meta?

thanks for all the help!

Alpha carbonyl hydrogens are naturally acidic and the carbanion is stabalized by resonance to the carbonyl group. H3O+ is the acid catalyst for the reaction.

 

[doc3232]

I am rusty on this but the acid (H3O) forces enol formation.
which is basically CH2 -C(-OH) -CH -CH2 (this has a double bond).
Then Cl can come in at the double bond.

I hope I made sense.

 

[Philippines03j]

I beleive you use ortho and para while refering to a benzene ring with a substituent not cyclohexanes.

 

[Kneecoal]

Alpha carbonyl hydrogens are naturally acidic and the carbanion is stabalized by resonance to the carbonyl group. H3O+ is the acid catalyst for the reaction.

thanks. that makes sense.

I beleive you use ortho and para while refering to a benzene ring with a substituent not cyclohexanes.

yyyikes. you're right.