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

Verified step by step guidance

1. Identify the number of unique carbon environments from the 'all' spectrum. There are four distinct peaks, indicating four unique carbon environments.
2. Determine the types of carbons present using the DEPT spectra. The CH3 spectrum shows one peak, indicating one methyl group. The CH2 spectrum shows one peak, indicating one methylene group. The CH spectrum shows one peak, indicating one methine group. The remaining peak in the 'all' spectrum that does not appear in the DEPT spectra corresponds to a quaternary carbon.
3. Analyze the chemical shifts of the peaks. The peak around 210 ppm is characteristic of a carbonyl carbon (C=O), likely a ketone or aldehyde. The peaks around 130-140 ppm suggest the presence of a double bond (C=C). The peaks around 20-40 ppm are typical for alkyl carbons.
4. Combine the information to deduce the structure. The molecular formula C6H10O suggests a degree of unsaturation of 2 (one for the carbonyl group and one for the double bond). The presence of a carbonyl group, a double bond, and the specific types of carbons (CH3, CH2, CH, and quaternary) should guide you to the correct structure.
5. Propose a structure that fits all the data. Consider common structures with the given molecular formula and the identified functional groups and carbon environments. Verify that the proposed structure matches the DEPT NMR data and the molecular formula.

Key Concepts

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 13C NMR Spectroscopy

DEPT (Distortionless Enhancement by Polarization Transfer) 13C NMR is a technique used to differentiate between carbon environments in organic compounds. It allows for the identification of CH3, CH2, and CH groups based on the intensity of the signals. This information is essential for deducing the structure of the compound by revealing how many of each type of carbon are present.

Chemical Shifts in NMR

Chemical shifts in NMR spectroscopy refer to the position of the peaks in the spectrum, measured in parts per million (ppm). Different types of carbon atoms resonate at different chemical shifts due to their electronic environments. For example, sp3 hybridized carbons (like those in CH3 and CH2 groups) typically appear in the 0-100 ppm range, while sp2 carbons (like those in alkenes) appear at higher ppm values, aiding in structural determination.