Topic: Friedel Craft reaction question (Read 2823 times)

pigeonsATW · « **on:** February 17, 2013, 02:05:39 PM »

I'm not sure which ring the CH₃CO would attach to. Also, how would I know whether COC1=CC=CC=C1

or

has a stronger influence on the regiochemistry of the reaction?
Thanks

Mod edit: IMG code. Dan

orgopete · « **Reply #1 on:** February 17, 2013, 03:10:43 PM »

A Friedel-Crafts is an electrophilic reaction. Which ring do you think would be a better electron donor?

pigeonsATW · « **Reply #2 on:** February 17, 2013, 04:31:33 PM »

Quote from: orgopete on February 17, 2013, 03:10:43 PM

A Friedel-Crafts is an electrophilic reaction. Which ring do you think would be a better electron donor?

OK I might be completely off here, but this is what I think... The resonance structures for anisole gives a negative charge on the ortho and para Carbons, making these atoms electron donors.
$C\[O+]=C1/[CH-]C=CC=C1$

$C\[O+]=C1\[CH-]C=CC=C1$
Similarly resonance structures for nitrobenzene give a positive charge on the ortho and para Carbons. (poor electron donors).
[O-][N+]([O-])=C1[CH+]C=CC=C1

And as nitrobenzene is attached to the meta position of anisole it has no electrons that it can donate to nitrobenzene.
This eliminates A, B and D.
Of C and E, I'm assuming steric hindrance plays a part in making E more favorable.
Please confirm whether my long winded explanation makes sense / is correct.

Thanks!

Dan · « **Reply #3 on:** February 17, 2013, 05:28:56 PM »

Quote from: acidic_pigeon_shit on February 17, 2013, 04:31:33 PM

Please confirm whether my long winded explanation makes sense / is correct.

Sounds sensible to me.

Topic: Friedel Craft reaction question (Read 2823 times)

pigeonsATW

Friedel Craft reaction question

orgopete

Re: Friedel Craft reaction question

pigeonsATW

Re: Friedel Craft reaction question

Dan

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