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Exam 15: Nmr Spectroscopy

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Question 21

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Determine the number of signals for 4-methyl-1-propylbenzene in the ¹H NMR spectrum.

A) 4
B) 5
C) 6
D) 7
E) 8

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Question 22

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Provide the structure that is consistent with the data below. C₅H₁₀O₂ IR (cm^-1): 2950, 1720 ¹H NMR (δ): 3.6 (s, 3H), 2.5 (septet, 1H), 0.9 (d, 6H) ¹³C NMR (δ): 190 (s), 55 (q), 40 (d), 16 (q)

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Question 23

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Deduce the identity of the following compound from the spectral data given. C₉H₁₀O₂: ¹³C NMR, δ 18.06 (quartet), 45.40 (doublet), 127.32 (doublet), 127.55 (doublet), 128.61 (doublet), 139.70 (singlet), 180.98 (singlet); IR, broad 3500-2800, 1708 cm^-1

What information does a COSY spectrum give?

How many signals would you expect to see in the ¹H NMR spectrum of the following compound?

Deduce the identity of the compound from the data provided. C₁₀H₁₄O: IR (cm^-1): 3200-3500 (broad), 3050, 2950, 1610 ¹H NMR(δ): 1.0 (s, 6H), 2.0 (s, 3H), 2.8 (broad s, 1H), 7.3 (d, 2H), 7.6 (d, 2H)

What multiplicities are observed in the spin coupled ¹³C NMR spectrum of 2,3-dimethyl-2-butene?

Provide the structure that is consistent with the data below. C₅H₈Cl₂ IR (cm^-1): 2950 ¹H NMR (d): 1.4 (4H, t), 1.2 (4H, t) ¹³C NMR (d): 62 (s), 26 (t), 23 (t)

Give the structure of a compound that has a formula of C₈H₁₀O₂ and has signals in the ¹³C NMR spectrum at 54.8 ppm (CH₃) , 63.3 ppm (CH₂) , 113.6 ppm (CH) , 128.3 ppm (CH) , 134.11 ppm (C) , and 158.6 ppm (C) .

________ is commonly used as an internal reference in NMR spectroscopy; its signal is assigned in ¹H and ¹³C NMR spectroscopy.

Deduce the identity of the following compound from the ¹H NMR data given. C₄H₇BrO: δ 2.2 (3H, singlet), 3.5 (2H, triplet), 4.5 (2H, triplet)

Provide the structure that is consistent with the data below. C₇H₁₄O₂ IR (cm^-1): 2950, 1750 ¹H NMR (d): 2.3 (2H, q), 1.0 (3H, t), 0.9 (9H, s) ¹³C NMR (d): 185 (s), 78 (s), 29 (t), 14 (q), 12 (q)

Which of the following protons gives an NMR signal with the highest chemical shift value (farthest downfield) ? (CH₃) ₂CH-O-CH₂CH₂CH₃ 1 2 3 4 5

Provide the structure that is consistent with the data below. C₅H₁₀O₂ IR (cm^-1): 3300-2800 (v. broad), 2950, 1710 ¹H NMR (δ): 12.0 (broad s, 1H), 0.9 (s, 9H) ¹³C NMR (δ): 220 (s), 45 (s), 12 (q)

Give the structure of a compound that has a formula of C₄H₇ClO₂ and has a triplet (3H, 1.1 ppm) , quintet (2H, 1.2 ppm) , triplet (1H, 4.4 ppm) , and singlet (1H, 11.6 ppm) in the ¹H NMR spectrum.

Deduce the identity of the compound from the data provided. C₅H₈O₄: IR (cm^-1) : 2800-3300 (broad) , 2950, 1740 ¹³C NMR (δ, splitting) : 17.3 (q) , 44.3 (s) , 210.5 (s)

Give the structure for the compound that has a formula of C₁₀H₁₂O and the following ¹H NMR and ¹³C NMR spectra. Label the hydrogens and the carbons. ¹H NMR: 1.2 ppm (t, 3H); 2.3 ppm (s, 3H); 2.6 ppm (q, 2H), 7.2 ppm (d, 2H), and 7.8 ppm (d, 2H). ¹³C NMR: 7.0 ppm (CH₃); 20.9 ppm (CH₃); 32.0 ppm (CH₂); 128.0 (CH), 129.1 ppm (CH), 134.0 ppm (C); 141.0 ppm(C); and 198.1 ppm (C).

What splitting pattern is observed in the proton NMR spectrum for the indicated hydrogens?

Provide the structure that is consistent with the data below. C₅H₁₀O IR (cm^-1): 2950 ¹H NMR (d): 3.5 (4H, s), 0.9 (6H, s) ¹³C NMR (d): 64 (t), 41 (s), 12 (q)

How many signals would you expect to see in the ¹H NMR spectrum of the following compound? CH₃CH₂CH₂CH₃