A compound was isolated and determined to have a molecular formula of C_6H_6Br_2

Question

A compound was isolated and determined to have a molecular formula of C_6H_6Br_2O by high resolution mass spectrometry. Use the following spectra to elucidate the structure of the compound. Determine the degrees of unsaturation and identify the diagnostic absorption(s) in the IR. Identify possible substructure(s) from the combined inferences derived from the IR and H NMR spectra. Now consider various structural possibilities. Write your deduced structure and provide confirming proton assignments a-c by placing the designated letters with the respective protons in your deduced structure.

Explanation / Answer

Answer: C4H6Br2O: Based on given spectral data it is a carbonyl compound.

The compund is CaH2(Br)-CbH2-C(=O) - CcH2 - Br :

The 2 - hydrogens on Ca and Cb are triplet whereas 2 - hydrogens on Cc are singlet.

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