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What are the possible sites of iodination of the salicylamide ring?
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How many possible atom arrangements are there for a molecule with 5 carbons with one ring?
For hydrocarbon molecules, the smallest possible ring contains 3 carbon atoms. This ring can be substituted with one ethyl group or two methyl groups. In a three carbon ring, all possible substitution positions are chemically equivalent. A four carbon atom-containing ring can be substituted with only one external carbon within the constraints given in the question, and all its positions of possible substitution are chemically equivalent. A five carbon atom-containing ring can not be substituted with any additional carbon atoms, within the constraints given in the question. Therefore, there are only four possible hydrocarbons within the constraints given in the question: ethyl cyclopropane, dimethyl cyclopropane, ethyl cyclobutane, and cyclopentane. There are many more possible atom arrangements if atoms of additional elements are allowed.
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What is the most likely site of iodination in an iodination of salicylamide experiment and why?
I guess you could end up with either a 1,2,3-trisubstituted or 1,2,4-trisubstituted ring, but the main product in my experiment was 2-hydroxy-5-iodobenzamide (a 1,2,4-trisubstituted ring) determined by the ortho/para-directing hydroxyl group at the C1 carbon, coupled with the meta-directing amide at the C2 (both directing substitution to the C4 position), and then narrowed down to a specific position by the 816.28 cm^-1 strong peak that was on the fingerprint region of my IR spectra that is characteristic of a 1,2,4-trisubstituted ring. Also, if you draw out the carbocation intermediates you can see that the positive charge would not end up on the C2, which is the most likely scenario when you consider the C2 is already partially positive due to the electron withdrawing amide that is attached to it.
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