PAL Worksheet Proton NMR and combined practice problems Write out the answers on separate sheets of paper. 1. How many signals will there be in the 1H NMR spectrum of each of these compounds? 2. Propose a structure that is consistent with each set of data. a. C4H10O 1 H NMR spectrum singlet  singlet  1.28 (9H) 1.35 (1H) b. C7H15Cl 1 H NMR spectrum singlet  singlet  1.10 (9H) 1.60 (6H) c. C2H4Br2 1 H NMR spectrum doublet  quartet  2.50 (3H) 5.90 (1H) d. C4H8Cl2 1 H NMR spectrum doublet  quartet  triplet  sextet  1.60 (3H) 2.15 (2H) 3.72 (2H) 4.27 (1H) e. C5H8Br4 1 H NMR spectrum singlet  f. C4H9Br 3.60 (8H) 1 H NMR spectrum doublet  multiplet  doublet  1.10 (6H) 1.90 (1H) 3.40 (2H) g. C5H11Br 1 H NMR spectrum singlet  singlet  1.10 (9H) 3.20 (2H) h. C7H14 1 H NMR spectrum singlet  singlet  doublet  doublet  1.10 (9H) 1.60 (3H) 4.60 (1H) 4.80 (1H) i. C4H8O 1 H NMR spectrum triplet  singlet  quartet  1.10 (3H) 2.10 (3H) 2.40 (2H) j. C7H14O 1 H NMR spectrum triplet  sextet  quartet  0.90 (6H)  (4H) 2.40 (4H) k. C5H10O2 1 H NMR spectrum triplet  multiplet  multiplet  triplet  singlet  l. C6H12O2 1 H NMR spectrum 0.94 (3H) 1.39 (2H) 1.62 (2H) 2.35 (2H) 12.0 (1H) singlet singlet singlet    1.08 (9H) 2.23 (2H) 12.1 (1H) m. C5H8O4 1 H NMR spectrum triplet  multiplet  triplet  singlet  0.93 (3H) 1.80 (2H) 3.10 (1H) 12.70 (2H) n. C6H12O2 1 H NMR spectrum doublet  triplet  multiplet  quartet  1.18 (6H) 1.26 (3H) 2.51 (1H) 4.13 (2H) o. C7H12O4 1 H NMR spectrum triplet  singlet  quartet  1.28 (6H) 3.36 (2H) 4.21 (4H) p. C7H14O2 1 H NMR spectrum doublet  multiplet  multiplet  singlet  triplet  0.92 (6H) 1.52 (2H) 1.70 (1H) 2.09 (3H) 4.10 (2H) 3. Each compound gives only one signal in its 1H NMR spectrum. Propose a structure for each. a. C3H6O b. C5H10 c. C5H12 d. C4H6Cl4 4. Propose a structure that is consistent with the data provided (IR, Mass Spec, 1H NMR, 13 C NMR, and molecular formula).