Question 16.61: Deduce the structure of a compound with the molecular formul......

Organic Chemistry Study Guide: Key Concepts, Problems, and Solutions [1424398]

Deduce the structure of a compound with the molecular formula C₄H₆Cl₂O based on the following proton NMR spectrum.

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The spectrum contains a low-field singlet at ~5 d and two triplets centered at 3.85 d. The two identical triplets correspond to two methylene groups. One of them is bonded to a choline atom, the other to an oxygen atom. The low-field singlet also contains two hydrogen atoms. The compound is Cl-CH₂-O-CH₂CH₂-Cl.

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