Solve the structure of the unknown. Show proposed structure of unknown compound

Question

Solve the structure of the unknown. Show proposed structure of unknown compound with (i) proton nmr assignments and (ii) carbon nmr assignments. Name the structure of the unknown compound (molar mass of compound is 120).

1. Predict the peak position of key IR absorption bands. 2. Label all non-equivalent carbon atoms. 3. Predict 13 peak positions. 4. Label all non-equivalent hydrogen atoms. 5. Predict HNMR peak positions and integration. 6. Identify the number of nearest neighbor hydrogens for every peak. 7. Predict peak multiplicity using the n 1 rule. 8. List all the functional groups

Explanation / Answer

A doublet at 1.22 ppm for 6H and a quintet at 2.9 ppm for 1H indicates an isopropyl group. A multiplet at 7.1 -7.3 ppm for 5H indicates a phenyl ring. Combining these two fragments will give isopropyl benzene with molecular weight 120. So, the compound is isopropyl benzene. 1H NMR; 1.2 ppm (6H, 2CH3), 2.9 ppm (1H, CH), 7.1-7.3 ppm (5H, phenyl). 13C NMR; 22 ppm (2CH3), 45 ppm (CH), 4signals for aromatic carbon

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