Problem: Draw a mechanism that supports the formation of the particular regiochemistry that you observe for your product (5-iodosalicylamide is the product ((i.e. Iodine attached at the meta position)), salicylamide is the starting material, NaI is the source of iodine, NaOCl is the oxidizing agent, and ethanol is the solvent). Be sure to include any important intermediates and resonance structures.

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FREE Expert Solution

For this problem, we have to draw the mechanism if the formation of 5-iodosalicylamide from salicylamide and NaI/NaOCl:

  • This reaction will follow an EAS iodination where I2 is prepared from NaI and NaOCl
  • I from I2 is electrophilic enough to be attacked by the ring.
  • The attachment of I will proceed via directing effects of either -CONH2 or -OH
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Problem Details

Draw a mechanism that supports the formation of the particular regiochemistry that you observe for your product (5-iodosalicylamide is the product ((i.e. Iodine attached at the meta position)), salicylamide is the starting material, NaI is the source of iodine, NaOCl is the oxidizing agent, and ethanol is the solvent). Be sure to include any important intermediates and resonance structures.

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What scientific concept do you need to know in order to solve this problem?

Our tutors have indicated that to solve this problem you will need to apply the EAS: Badass Activity Chart concept. If you need more EAS: Badass Activity Chart practice, you can also practice EAS: Badass Activity Chart practice problems.

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Our tutors rated the difficulty ofDraw a mechanism that supports the formation of the particul...as medium difficulty.

What professor is this problem relevant for?

Based on our data, we think this problem is relevant for Professor Daoudi's class at UCF.