Chapter 13: Problem 2
State the number of sets of equivalent hydrogens in each compound and the number of hydrogens in each set. (a) 3-Methylpentane (b) \(2,2,4\)-Trimethylpentane
Chapter 13: Problem 2
State the number of sets of equivalent hydrogens in each compound and the number of hydrogens in each set. (a) 3-Methylpentane (b) \(2,2,4\)-Trimethylpentane
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Get started for freeThe \({ }^{13} \mathrm{C}-\mathrm{NMR}\) spectrum of 3 -methyl-2-butanol shows signals at \(\delta 17.88\left(\mathrm{CH}_{3}\right), 18.16\) \(\left(\mathrm{CH}_{3}\right), 20.01\left(\mathrm{CH}_{3}\right), 35.04\) (carbon-3), and \(72.75\) (carbon-2). Account for the fact that each methyl group in this molecule gives a different signal.
The natural abundance of \({ }^{13} \mathrm{C}\) is only \(1.1 \%\). Furthermore, its sensitivity in NMR spectroscopy (a measure of the energy difference between a spin aligned with or against an applied magnetic field) is only \(1.6 \%\) that of \({ }^{1} \mathrm{H}\). What are the relative signal intensities expected for the \({ }^{1} \mathrm{H}-\mathrm{NMR}\) and \({ }^{13} \mathrm{C}-\mathrm{NMR}\) spectra of the same sample of \(\mathrm{Si}\left(\mathrm{CH}_{4}\right)_{4}\) ?
The line of integration of the two signals in the \({ }^{1} \mathrm{H}-\mathrm{NMR}\) spectrum of a ketone with the molecular formula \(\mathrm{C}_{7} \mathrm{H}_{14} \mathrm{O}\) rises 62 and 10 chart divisions, respectively. Calculate the number of hydrogens giving rise to each signal and propose a structural formula for this ketone.
Calculate the index of hydrogen deficiency of these compounds. (a) Aspirin, \(\mathrm{C}_{9} \mathrm{H}_{8} \mathrm{O}_{4}\) (b) Ascorbic acid (vitamin \(\mathrm{C}\) ), \(\mathrm{C}_{6} \mathrm{H}_{8} \mathrm{O}_{6}\) (c) Pyridine, \(\mathrm{C}_{5} \mathrm{H}_{5} \mathrm{~N}\) (d) Urea, \(\mathrm{CH}_{4} \mathrm{~N}_{2} \mathrm{O}\) (e) Cholesterol, \(\mathrm{C}_{27} \mathrm{H}_{46} \mathrm{O}\) (f) Dopamine, \(\overline{\mathrm{C}}_{\mathrm{g}} \mathrm{H}_{11} \mathrm{NO}_{2}\)
Explain how to distinguish between the members of each pair of constitutional isomers based on the number of signals in the proton-decoupled \({ }^{13} \mathrm{C}\)-NMR spectrum of each member.
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