Determine the ratios of the chemically nonequivalent protons in a compound if the steps of the integration curves measure 40.5, 27, 13, and 118 mm, from left to right across the spectrum. Draw the structure of a compound whose ¹H NMR spectrum would show these integrals in the observed order.

How can ¹H NMR distinguish between the compounds in each of the following pairs?

g.

Answer the following questions:

c. What is the relationship between coupling constant in hertz and operating frequency?

d. How does the operating frequency in NMR spectroscopy compare with the operating frequency in IR and UV/Vis spectroscopy?

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

b. <IMAGE>

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

a. <IMAGE>

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

b. <IMAGE>

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

c. <IMAGE>

Identify each of the following compounds from the ¹H NMR data and molecular formula:

b. C₈H₉Br: a 3H doublet at 2.01 ppm a 1H quartet at 5.14 ppm

a 5H broad singlet at 7.35 ppm

Identify each of the following compounds from the ¹H NMR data and molecular formula:

c. C₅H₁₀O₂: a 3H triplet at 1.15 ppm

a 3H triplet at 1.25 ppm

a 2H quartet at 2.33 ppm

a 2H quartet at 4.13 ppm

Identify the compound with molecular formula C₇H₁₄O that gives the following proton-coupled ¹³C NMR spectrum:

<IMAGE>

Compound A, with molecular formula C₄H₉Cl, shows two signals in its ¹³C NMR spectrum. Compound B, an isomer of compound A, shows four signals, and in the proton-coupled mode, the signal farthest downfield is a doublet. Identify compounds A and B.

Would it be better to use ¹H NMR or ¹³C NMR spectroscopy to distinguish 1-butene, cis-2-butene, and 2-methylpropene? Explain your answer.

An alkyl halide reacts with an alkoxide ion to form a compound whose ¹H NMR spectrum is shown here. Identify the alkyl halide and the alkoxide ion. (Hint: See Section 9.15.)

<IMAGE>

The ¹H NMR spectra of three isomers with molecular formula C₇H₁₄O are shown here. Which isomer produces which spectrum?

b. <IMAGE>

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

b. C₆H₁₂O₂

<IMAGE>

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

d. C₄H₈O₂

<IMAGE>

The ¹H NMR spectrum of 2-propen-1-ol is shown here. Indicate the protons in the molecule that are responsible for each of the signals in the spectrum.

<IMAGE>

Draw a splitting diagram for the H_b proton if J_bc = 10 and J_ba = 5.

Sketch the following spectra that would be obtained for 2-chloroethanol:

a. The ¹H NMR spectrum for an anhydrous sample of the alcohol.

Sketch the following spectra that would be obtained for 2-chloroethanol:

b. The ¹H NMR spectrum for a sample of the alcohol that contains a trace amount of acid.

Sketch the following spectra that would be obtained for 2-chloroethanol:

c. The ¹³C NMR spectrum.

Sketch the following spectra that would be obtained for 2-chloroethanol:

d. The proton-coupled ¹³C NMR spectrum.

Sketch the following spectra that would be obtained for 2-chloroethanol:

e. The four parts of a DEPT ¹³C NMR spectrum.

How can ¹H NMR be used to prove that the addition of HBr to propene follows the rule that says that the electrophile adds to the sp² carbon bonded to the most hydrogens?

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

b. C₆H₁₂O

<IMAGE>

Calculate the amount of energy (in calories) required to flip an ¹H nucleus in an NMR spectrometer that operates at 300 MHz.

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

c. <IMAGE>

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

d. <IMAGE>

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 the compound with molecular formula C₆H₁₀O that gives the following DEPT ¹³C NMR spectrum:

<IMAGE>