anonymous
  • anonymous
ORGANIC: why does vanillin direct to the 5 spot upon bromonation (5-bromo-vanillin) instead of the 2 or 6 spot?
Chemistry
  • Stacey Warren - Expert brainly.com
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SOLVED
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jamiebookeater
  • jamiebookeater
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anonymous
  • anonymous
there are 2 o/p directors and only 1 meta director so?
anonymous
  • anonymous
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raspberryjam
  • raspberryjam
Well it's gonna wanna go ortho to the -OH group because hydroxyl groups are very strong activators. In the 5 spot it is also meta to the -CHO group. It's probably not gonna want to go to the 2 spot because even though the -OCH3 group is a strong o/p director there's too much steric hindrance with the -CHO group. Putting it at the 6 spot would put it ortho to the -CHO group (which doens't make sense because that group is meta directing), para to the -OCH3 group and meta to the hydroxyl group (doesn't make sense because that group is o/p directing)

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raspberryjam
  • raspberryjam
You wanna look at the strongest activating group which in this is the hydroxyl group. Putting it at the 5 spot is good for two reasons 1. ortho to the -OH 2. meta to the -CHO group
raspberryjam
  • raspberryjam
And also the 5 spot isn't crowded like the 2 spot is
anonymous
  • anonymous
THANKS! this confirmed my suspicions but thanks for the full explanation!

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