1. Draw and name the following: a. C5H8O, IR 1750 cm-1 b. C3H6O, IR 1720 cm-1, 1H NMR is a singlet c. C3H6O, IR 1620 cm-1, NMR 4.0 ppm (s, 3H; other peaks not given)

Figure 13-9 CsH10O 9 HSP-47-026 8 00 7 6 5 ppm elle 3 2 2 3 1 O A. B. c. D.

13. Propose structures for compounds that fit the following ¹H NMR data: a. CH, Br a. 3H doublet at 2.0 b. 1H quartet at 5.0 C. 5H singlet at 7.3 8 b. C15H240 a. 18H singlet at 1.41 8 b. 3H singlet at 1.6 8 2H singlet at 6.97 8 C. d. 1H singlet at 4.5

ee ? 17. Which of the following agrees with ¹H NMR spectrum shown below: 3H 2H 3H singlet sextet 2 PPM all B) may D) O. and OH sloni triplet 3 xnG od to doid bevised O A) oldsta ton ei be H₂ Hlo als C) ortune or Je D) 2H triplet #76

A1

III Predict the 'H NMR integration ratio for the following structure. D C 1.0 H A II. 2 H III. 3 H 1. 2 H B II. 2 H III. 2 H 1. 0 H II. 2 H III. 2 H I. 1 H II. 2 H III. 3 H

17. The following proton NMR spectrum of a compound of molecular formula C3H8O 10 9 ©2017 Pearson Education, Inc. 8 6 H3C OHz H 50Hz 4.18 4.08 5 8 (ppm) 4 OHz 50Hz 1.38 1.28 a) Propose a structure for this compound. (Hint: Find IHD first) C+1-H+1/2/2 3+1-1/2 3 O (b) Assign peaks to show which protons give rise to which signals in the spectrum 0

b) Given the structure of the hydrocarbon below: CH3CH2CI i. How many peaks will this compound produce in an NMR spectrum and why? ii. What will be the relative sizes of the peaks? Explain iii. Using the n+ 1 rule, how many splits will there be in each peak?

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Which of the following molecules produced the 1H NMR spectrum shown below? (key: s = singlet, d = doublet, t = triplet, q = quartet, sept = septet, dd = doublet of doublets, br = broad singlet, m = multiplet) 2H, q 1H, q Cil 1H, br PPM 8 A. B. C. D. 2H, d 2H, d MeO 7 6 OH OH 3H, d 2 3H, t