15. Analytical Techniques:IR, NMR, Mass Spect

Which of the following compounds is responsible for the ¹H NMR spectrum shown below?

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

b. C₅H₁₀O

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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:

n.

The following ¹H NMR spectra are for four compounds, each with molecular formula of C₆H₁₂O₂. Identify the compounds.

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When compound A (C₅H₁₂O) is treated with HBr, it forms compound B (C₅H₁₁Br). The ¹H NMR spectrum of compound A has a 1H singlet, a 3H doublet, a 6H doublet, and two 1H multiplets. The ¹H NMR spectrum of compound B has a 6H singlet, a 3H triplet, and a 2H quartet. Identify compounds A and B.

Identify each of the following compounds from its molecular formula and its IR and ¹H NMR spectra:

d. C₁₁H₁₄O₂

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In the lab, ¹H NMR is often used to verify that a reaction has worked as expected by comparing the product spectrum with what is expected. Given the ¹H NMR of the reactant shown, draw the spectrum you'd expect to see of the product that results.

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(a) Using the ¹H NMR spectra, identify the reactants and product for this reaction.

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(b) Provide an arrow-pushing mechanism for the reaction.

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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.]

Draw the ¹H NMR spectrum you would expect to see for each of the molecules in Assessment 15.63.

(b)

Draw the ¹H NMR spectrum you would expect to see for each of the molecules in Assessment 15.63.

(c)

Draw the ¹H NMR spectrum you would expect to see for each of the molecules in Assessment 15.63.

(d)

Draw a spectrum for each of the following molecules, being sure to indicate the multiplicity, integration, and chemical shift of each peak. Label each signal based on the set of equivalent hydrogens to which it corresponds.

(b)

Draw a spectrum for each of the following molecules, being sure to indicate the multiplicity, integration, and chemical shift of each peak. Label each signal based on the set of equivalent hydrogens to which it corresponds.

(c)