Identify each compound from its molecular formula and its 1H NMR spectrum: b. C5H10O

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Determine the degree of unsaturation: Calculate the degree of unsaturation (also known as the index of hydrogen deficiency, IHD) using the formula: IHD = (2C + 2 + N - H - X)/2, where C is the number of carbons, N is the number of nitrogens, H is the number of hydrogens, and X is the number of halogens. For C5H10O, the IHD is (2*5 + 2 - 10)/2 = 1, indicating one double bond or ring.

Analyze the 1H NMR spectrum: Look for key features in the 1H NMR spectrum such as chemical shifts, multiplicity, and integration. Chemical shifts can indicate the environment of the protons (e.g., alkyl, alcohol, carbonyl). Multiplicity (singlet, doublet, triplet, etc.) can provide information about neighboring protons. Integration gives the relative number of protons for each signal.

Consider possible functional groups: With an IHD of 1 and the presence of oxygen, consider functional groups such as alcohols, ethers, or carbonyls (aldehydes or ketones). The 1H NMR spectrum can help distinguish between these. For example, a broad singlet around 1-5 ppm could indicate an alcohol, while a signal around 9-10 ppm could suggest an aldehyde.

Propose possible structures: Based on the IHD and 1H NMR analysis, propose possible structures for C5H10O. Consider common structures like pentan-2-one, pentan-3-one, or cyclopentanol, and use the NMR data to support or refute these possibilities.

Verify with NMR data: Cross-check the proposed structures with the NMR data. Ensure that the number of signals, their chemical shifts, multiplicities, and integrations match the expected pattern for the proposed structure. This step helps confirm the identity of the compound.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Molecular Formula Interpretation

The molecular formula provides essential information about the number and types of atoms in a compound. For C5H10O, it indicates that the compound contains five carbon atoms, ten hydrogen atoms, and one oxygen atom. Understanding how to interpret this formula is crucial for deducing possible structural isomers and functional groups present in the compound.

Nuclear Magnetic Resonance (NMR) Spectroscopy

NMR spectroscopy is a powerful analytical technique used to determine the structure of organic compounds. The 1H NMR spectrum specifically provides information about the hydrogen atoms in a molecule, including their environment and connectivity. Peaks in the spectrum correspond to different hydrogen environments, allowing chemists to infer structural details such as the presence of functional groups and the arrangement of atoms.

Isomerism in Organic Compounds

Isomerism refers to the existence of compounds with the same molecular formula but different structural arrangements or spatial orientations. For C5H10O, various isomers can exist, including alcohols, ethers, and ketones. Recognizing the potential for isomerism is essential for accurately identifying the compound based on its molecular formula and NMR data.