has just made a bromotoluene boili can also be used to derivatize an unknown liq
ID: 1035330 • Letter: H
Question
has just made a bromotoluene boili can also be used to derivatize an unknown liquid. For example, a student ehie product in the lab. This product is a liquid an the student finds the the la ng point of this liquid product to be in the lowl80s"C. Here's the problem: BP. 181 ? ??. 1830C BP, 185°C Br Br Do some rescarch could help with this identification. Report the melting point data you find of your own to investigate how the nitration of their bromotoluene compound HW2. Explain why FT-IR was not largely used to determine the major product of the nitration reaction you performed in the lab. HW3. Esplain why GC-MS was not largely used to determine the major product of the nitration reaction you performed in the lab. HW4. Had we started the reaction with nitrobenzene and attempted a Friedel Crafts Acylation to obtain the same major product, would we have been as successful? Explain. AICl NO2 NO2Explanation / Answer
1. Nitration of o-bromotoluene yields 2-bromo-4-nitrotoluene with melting point 76-77 oC
Nitration of m-bromotoluene yields 3-bromo-4-nitrotoluene with melting point 86-88 oC
Nitration of p-bromotoluene yields 4-bromo-2-nitrotoluene with melting point 45-48 oC
Hence the compounds can easily be identified by nitration as they all yield products with very different melting points.
2. All the products have the same functional groups, such that have aromatic ring, -NO2 group, therefore, the IR spectrum for all the compounds would almost be the same and not used for identification of compounds.
3. The boiling points for all the nitration products is extremely high. that is the compounds cannot be vaporized and converted to gas phase as needed by GC for analysis. Hence gas chromatography is not employed.
4. -NO2 group on the ring is strongly electron withdrawing and substiution of it with another strongly electrophilic acyl substituent is very difficult and would ne taken place sucessfully.
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