Propose a reasonable structure based on the molecular formula, the 1H NMR, and the proton–decoupled 13C NMR data below. The unknown compound has a molecular formula of C7H16O and * = CH2 by DEPT. 1H NMR 2 H 3 H 8 H 2 H 1 H (CH3)4 Si 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 300-MHz 1H NMR spectrum ppm (?) 13C NMR * * * * * * 60 40 20 0 13C NMR spectrum ppm (?) OH
Added by Michele F.
Close
Step 1
The molecular formula C6H16O suggests that the compound is likely an alcohol (due to the presence of oxygen) and is saturated (no double or triple bonds, as indicated by the hydrogen count). Show more…
Show all steps
Your feedback will help us improve your experience
Sri K and 88 other Chemistry 101 educators are ready to help you.
Ask a new question
Labs
Want to see this concept in action?
Explore this concept interactively to see how it behaves as you change inputs.
Key Concepts
Recommended Videos
Propose a structure consistent with each set of data. a. Compound $\textbf{J}$: molecular ion at 72; IR peak at 1710 $cm^{-1}$; $^1H$ NMR data (ppm) at 1.0 (triplet, 3 H), 2.1 (singlet, 3 H), and 2.4 (quartet, 2 H) b. Compound $\textbf{K}$: molecular ion at 88; IR peak at 3600-3200 $cm^{-1}$; $^1H$ NMR data (ppm) at 0.9 (triplet, 3 H), 1.2 (singlet, 6 H), 1.5 (quartet, 2 H), and 1.6 (singlet, 1 H)
Propose a structure consistent with each set of data. a. A compound $\textbf{X}$ (molecular formula $C_6H_{12}0_2$) gives a strong peak in its IR spectrum at 17 40 $cm^{-1}$. The $^1H$ NMR spectrum of $\textbf{X}$ shows only two singlets, including one at 3.5 ppm. The $^{13}C$ NMR spectrum is given below. Propose a structure for $\textbf{X}$. b. A compound $\textbf{Y}$ (molecular formula $C_6H_{10}$) gives four lines in its $^{13}C$ NMR spectrum (27, 30, 67, and 93 ppm), and the IR spectrum given here. Propose a structure for $\textbf{Y}$.
Propose a structure consistent with each set of data. a. Compound $\textbf{A}$: Molecular formula: C$_8$H$_{10}$O IR absorption at 3150-2850 cm$^{-1}$ $^1$H NMR data: 1.4 (triplet, 3 H), 3.95 (quartet, 2 H), and 6.8-7.3 (multiplet, 5 H) ppm b. Compound $\textbf{B}$: Molecular formula: C$_9$H$_{10}$O$_2$ IR absorption at 1669 cm$^{-1}$ $^1$H NMR data: 2.5 (singlet, 3 H), 3.8 (singlet, 3 H), 6.9 (doublet, 2 H), and 7.9 (doublet, 2 H) ppm
Recommended Textbooks
Chemistry: Structure and Properties
Chemistry The Central Science
Chemistry
Transcript
Watch the video solution with this free unlock.
EMAIL
PASSWORD