Iodination of Salacylimide

Topics: Temperature, Fundamental physics concepts, Question Pages: 1 (279 words) Published: June 13, 2013
The Iodination of Salicylamide

Questions:
1. a) The possible sites of iodination of the salicylamide ring is on the ortho/para position to the -OH group.

b) The most likely site of iodination is the para position. This spot has the least steric hindrance and is favorable due to the directing effects of the -OH and the withdrawing effects from the carbonyl. 2. The homo surface shows that salicylamide has large electron density at the para and ortho positions. These sites are more likely to undergo the iodination, which supports the answer from question #1. 3. The ortho product has an energy of -145.38 KJ/Mol while the para product has an energy of -164.74 KJ/Mol. The lower energy of the para product makes it more favorable for its formation. This shows that the para product is more favorable due to its lower energy. This supports #1 because it shows that the para product is both kinetically and thermodynamically favored. 4. The reaction is under both the thermodynamic and kinetic control. From questions #2 and #3 it showed that the para product is more favorable due to having the lower energy than the ortho product and that there is a larger electron density in the o/p positions. 8. a) Salicylamide has a N-H stretch at ~3500cm-1, a C=O stretch at ~1600cm-1, and a -OH stretch at 3200cm-1. b) A strong peak from 730-770 cm-1 will indicate the substitution pattern of salicylamide. My purified product had a strong peak at 814cm-1 which indicate that it is 1,2,4-trisubstituted, indicating that the para product was formed.
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