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When toluene is treated with a mixture of excess sulfuric
Chapter 19, Problem 19.78(choose chapter or problem)
When toluene is treated with a mixture of excess sulfuric acid and nitric acid at high temperature, a compound is obtained that exhibits only two signals in its 1 H NMR spectrum. One signal appears upfield and has an integration of 3. The other signal appears downfield and has an integration of 2. Identify the structure of this compound and assign an IUPAC name.
Questions & Answers
QUESTION:
When toluene is treated with a mixture of excess sulfuric acid and nitric acid at high temperature, a compound is obtained that exhibits only two signals in its 1 H NMR spectrum. One signal appears upfield and has an integration of 3. The other signal appears downfield and has an integration of 2. Identify the structure of this compound and assign an IUPAC name.
ANSWER:Step 1 of 3
This question tells us that when toluene is treated with a mixture of excess sulfuric acid and nitric acid at high temperature, a compound is obtained that exhibits only two signals in its \({ }^{1} \mathrm{H}\) NMR spectrum. One signal appears upfield and has an integration of 3. The other signal appears downfield and has an integration of 2 . We're asked to identify the structure of this compound and to assign an IUPAC name.
Recall that toluene is the common name for methylbenzene. Methyl groups are ortho, para directors. A mixture of excess sulfuric and nitric acids places a nitro group at both ortho positions and at the para position.
The result is 2,4,6-trinitrotoluene (or TNT, as it’s commonly called).