Identify the compound with molecular formula C6H10O that gives the following DEPT 13C NMR spectrum:

Ch. 14 - NMR Spectroscopy

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Bruice 8th Edition

Ch. 14 - NMR Spectroscopy

문제 76

14장, 문제 76

Identify the compound with molecular formula C₆H₁₀O that gives the following DEPT ¹³C NMR spectrum:
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Analyze the molecular formula C6H10O. This indicates the compound contains six carbons, ten hydrogens, and one oxygen. The degree of unsaturation can be calculated using the formula: (2C + 2 - H)/2. For C6H10O, the degree of unsaturation is (2(6) + 2 - 10)/2 = 2, suggesting two double bonds, rings, or a combination thereof.

Interpret the DEPT 13C NMR spectrum. The 'all' spectrum shows four distinct peaks, indicating four unique carbon environments. The CH3 spectrum shows one peak, the CH2 spectrum shows one peak, and the CH spectrum shows one peak. This suggests the presence of one methyl group (CH3), one methylene group (CH2), and one methine group (CH). The remaining carbon is likely a quaternary carbon (not bonded to hydrogen).

Examine the chemical shift values. The peak near 200 ppm in the 'all' spectrum is characteristic of a carbonyl group (C=O). The peak near 140 ppm suggests a carbon in a double bond (likely part of an alkene). Peaks near 40-20 ppm correspond to sp3 hybridized carbons, such as CH3 and CH2 groups.

Combine the structural information. The presence of a carbonyl group (C=O) and an alkene (C=C) suggests the compound may be an α,β-unsaturated ketone. The sp3 carbons (CH3 and CH2) likely form part of the alkyl chain attached to the unsaturated system.

Propose a structure consistent with the data. Based on the molecular formula, degree of unsaturation, and DEPT NMR data, the compound is likely 3-hexen-2-one, which contains a ketone group, an alkene, and the appropriate number of CH3, CH2, and CH groups.

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Molecular Formula Interpretation

The molecular formula C6H10O indicates a compound containing six carbon atoms, ten hydrogen atoms, and one oxygen atom. Understanding the molecular formula is crucial for predicting the structure and reactivity of the compound. It provides insights into the degree of unsaturation, which can suggest the presence of double bonds or rings in the structure.

DEPT NMR Spectroscopy

DEPT (Distortionless Enhancement by Polarization Transfer) NMR is a technique used to differentiate between carbon types in a molecule. It provides information about the number of hydrogen atoms attached to each carbon atom, allowing for the identification of CH3, CH2, and CH groups. This information is essential for deducing the structure of the compound based on the observed signals in the spectrum.

Chemical Shift in NMR

Chemical shift refers to the resonant frequency of a nucleus relative to a standard in a magnetic field, measured in parts per million (ppm). In carbon NMR, different types of carbon atoms resonate at different chemical shifts based on their electronic environment. Analyzing the chemical shifts in the DEPT spectrum helps in identifying the types of carbon present in the compound and aids in constructing its molecular structure.

Identify the compound with molecular formula C6H10O that gives the following DEPT 13C NMR spectrum:<IMAGE>