15. Analytical Techniques:IR, NMR, Mass Spect

How many signals would the product of the following reaction show in

a. its ¹H NMR spectrum?

b. its ¹³C NMR spectrum?

Without worrying about the relative location of the signals (i.e., the chemical shift) or the splitting patterns, draw a spectrum of the following molecule, being sure to indicate the integration of each peak. Label each signal based on the set of equivalent hydrogens to which it corresponds. [We expand on this question in future assessments.]

The only organic compound obtained when compound Z undergoes the following sequence of reactions gives the ¹H NMR spectrum shown. Identify compound Z.

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The following NMR spectra correspond to compound of formula (C) C₆H₁₀O₂. Propose structure, and show how it is consistent with the observed absorptions.

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The ¹H NMR spectra of three isomers with molecular formula C₄H₉Br are shown here. Which isomer produces which spectrum?

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

b. C₅H₁₀O

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Draw the approximate positions that the following compound might show in its 1H NMR absorptions?

When a compound with molecular formula C₁₁H₁₄O₂ undergoes acid-catalyzed hydrolysis, one of the products that is isolated gives the following ¹H NMR spectrum. Identify the compound.

Explain how the following compounds, each with the same molecular formula, could be distinguished by their ¹H NMR spectra.

Match each of the ¹H NMR spectra with one of the following compounds:

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Describe the ¹H NMR spectrum you would expect for each of the following compounds, indicating the relative positions of the signals:

k.

Draw the approximate positions that the following compound might show in its 1H NMR absorptions?

Describe the ¹H NMR spectrum you would expect for each of the following compounds, indicating the relative positions of the signals:

f.

Identify pairs of coupled protons in the compound whose COSY spectrum is shown below.

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