Part I – Multiple Choice (3 points each)

Answer the questions by circling the correct answers here AND by shading them in on your SCANTRON.

NOTE: To select a choice higher than “e” (“ad” for example) shade in both letters for that choice (shade in both

“a” and “d” for example)

1. What will be the patterns in the 1H-NMR spectrum of 4-fluoro-4-propoxyheptane?

a) doublet, triplet b) doublet, quartet c) doublet, pentet d) doublet, sextet e) triplet, quartet

ab) triplet, pentet ac) triplet, sextet ad) quartet, pentet ae) quartet, sextet

2. How many signals appear in the proton-decoupled 13C NMR spectrum of 1,2-dibromobenzene?

a) 2 b) 3 c) 4 d) 5 e) 6 ab) 7 ac) 8

3. Which of the following compounds gives a 1H NMR spectrum consisting of doublets(s) and pentet(s)?

a) 1-bromo-1-chloropropane b) 1-bromo-2-chloropropane c) 2-bromo-2-chloropropane d) 1-bromo-3-chloropropane

4. What will be the patterns in the 1H-NMR spectrum of cyclopentadienone and how many signals would appear in

the proton-decoupled 13C NMR?

a) singlets only, 2 signals b) singlets only, 3 signals c) doublets only, 2 signals d) doublets only, 3 signals

e) singlet and triplet, 2 signals ab) singlet and triplet, 3 signals ac) doublet and triplet, 2 signals

ad) doublet and triplet, 3 signals

5. Which of the following correctly describes why tetramethylsilane has a 1H-NMR shift of 0.0 ppm and a normal

alkane has a shift of approximately 1 ppm?

a) Electrons are closer to the hydrogens in tetramethylsilane than in an alkane which makes it easier for the

electromagnetic field to penetrate.

b) Electrons are further away from the hydrogens in tetramethylsilane than in an alkane which makes it easier for the

electromagnetic field to penetrate.

c) Electrons are closer to the hydrogens in tetramethylsilane than in an alkane which makes it harder for the

electromagnetic field to penetrate.

d) Electrons are further away from the hydrogens in tetramethylsilane than in an alkane which makes it harder for the

electromagnetic field to penetrate.

6. Which compound below fits the following 1H-NMR data? Data: ppm, multiplicity, # of hydrogens:

0.8, triplet, 6H; 1.0, doublet, 3H; 1.5, nonet, 1H; 2.0, singlet, 3H; 2.1, doublet, 2H; 3.1, quartet, 1H; 7.0 triplet, 1H;

7.1, doublet, 2H; 7.2, singlet, 1H. All molecules below have the formula C14H20O.

7. Which compound below best matches the following spectrum? All molecules are C8H16O2.

8. Which compound below best matches the following spectrum? All molecules are C12H15ClO.

17. What is the index of hydrogen deficiency for a molecule with the formula C21H31F2N3O5?

a) 6 b) 7 c) 8 d) 9 e) 10 ab) 11 ac) 12 ad) 13 ae) 14 bc) 15 bd) 16 be) 17 cd) 18 de) 19

18. What is the index of hydrogen deficiency for R-1-cyclobutyl-3-oxo-1,4-diphenyloctanal?

a) 6 b) 7 c) 8 d) 9 e) 10 ab) 11 ac) 12 ad) 13 ae) 14 bc) 15 bd) 16 be) 17 cd) 18 de) 19

23. Which product(s) will result when Z-2-hexene is reacted with diazomethane?

I. (1R, 2R)-2-methyl-1-propylcyclopropane II. (1R, 2S)-2-methyl-1-propylcyclopropane

III. (1S, 2R)-2-methyl-1-propylcyclopropane IV. (1S, 2S)-2-methyl-1-propylcyclopropane

a) I only b) II only c) III only d) IV only e) I and II ab) I and III ac) I and IV ad) II and III ae) II and IV

bc) III and IV bd) I, II, and III be) I, II, and IV cd) I, III, and IV ce) II, III, and IV de) All of them