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2 Name Key 216 W13-Exam No. 1 Page 3 III. (17 points plus 3 bonus points) N-Benzylaniline can be prepared by reaction of benzyl chloride and aniline in the presence of aqueous sodium bicarbonate (NaC 3 ). Cl + N 2 + NaC 3 N + NaCl C 2 benzyl chloride aniline N-benzylaniline The procedure calls for 372 g of aniline, 127 g of benzyl chloride, and 105 g of sodium bicarbonate dissolved in 100 ml of water, and produces 160 g of N-benzylaniline. Write an answer in the box provided to each of the following questions. (1) (3 points) Calculate as to how many moles of each of the reagents are used in this procedure. Use the following atomic weights: C = 12, = 1, N = 1, = 16, Na = 23, Cl = 35.5 benzyl chloride: _1.00 moles; aniline: _.00 moles; NaC 3 : _1.25 moles (2) (3 points) What is the limiting reagent? benzyl chloride (3) (3 points) What is the theoretical yield of N-benzylaniline? Show your work. 183 g; 1.00 moles x 183 g/mole = 183 g () (2 points) What is the percentage yield of N-benzylaniline? Show your work. 87 %; (160 g / 183 g) x 100 = 87% (5) (3 points) About 260 g of aniline can be recovered from the reaction. Does this affect the calculation of theoretical yield? Explain. The recovered amount of aniline corresponds to 2.80 moles. Since in this experiment, mol equiv of aniline is used relative to the limiting reagent, benzyl chloride, it does not affect the calculation of theoretical yield. (6) (3 points) What volume of benzyl chloride (density 1.10 g/ml) is required for the reaction? 115. ml (7) (3 points; bonus question) Why is it necessary to use such a large excess of aniline for the reaction? Explain. As N-benzylaniline is more nucleophilic than the starting aniline, it can undergo multiple benzylations. By the use of a large excess of aniline, the overall reaction can be directed toward the monobenzylation of aniline.

3 Name Key 216 W13-Exam No. 1 Page IV. (15 points) n the basis of its spectroscopic information provided below, answer the following questions given and draw the structure of an unknown compound (C ; a strong IR absorption in the cm -1 region) in the box below. In addition, assign all 1 and 13 C peaks to the corresponding nuclei. Please note that one of the 1 peaks may be assignable to the hydrogen(s). 300 Mz 1 NMR spectrum in CDCl 3 (δ ppm) Proton-decoupled 13 C NMR spectrum in CDCl 3 (δ ppm) integration values The letter s, t, or q on top of each peak denotes the splitting pattern, singlet, triplet, or quartet, respectively, when the spectrum is run in the proton-coupled mode.! (1) (1 points) What is (are) the unit(s) of unsaturation of this compound? zero (2) (2 points) Does this compound have an ether (R--R ) group? N (3) ( points) What is the structure of () (8 points) Assign all 1 and 13 C chemical shifts to the compound? (no partial) the corresponding and C nuclei in the proposed structure. 2.8 ppm 3.55 ppm 1.35 ppm C C C 68 ppm C ppm ppm 1 C ppm C C 0.8 ppm 3.55 ppm 1.35 ppm 1 pt for each chem shift assignment 8

4 Name Key 216 W13-Exam No. 1 Page 5 V. (15 points) An unknown compound, C 9 12, has the following spectral properties. IR (neat): (broad and strong), (many medium strength peaks); no absorption peaks in the cm -1 region. 1 NMR in CDCl 3 : δ 1.89 (2, quintet, J = 7.0 z), 1.98 (1, s), 2.65 (2, t, J = 7.0 z), 3.60 (2, t, J = 7.0 z), and ppm (multiplets, 5 s). 13 C NMR in CDCl 3 : δ (t), 3.15 (t), (t), (d), (d), (d), and (s) ppm. The letters s, d, and t indicate splitting patterns when the spectrum is run under a proton-coupled mode. (1) (1 points) What is (are) the unit(s) of unsaturation of this compound? (2) (2 point) Does this compound have a benzene ring? Yes No (circle the one that applies) (3) (2 point) What does the IR spectrum tell you in terms of the presence of an -containing functional group in this molecule? (or hydroxyl) group () ( points) What is the structure of the (5) (6 points) Draw in the box below the structure compound? (no partial) you drew in () and assign all non-aromatic 1 peaks and the 13 C peaks at and ppm to the corresponding nuclei in the proposed structure ppm 2.65 ppm (t) 3.60 pm (t) ppm 1.98 ppm (s) 1.89 ppm (quintet) 1 pt for each chem shift assignment VI. (15 points) n the basis of its spectroscopic information provided below, answer the questions given on page 6 and draw the structure of an unknown compound (C ; IR a strong peak at 173 cm -1 ; no peaks in the cm -1 region) in the box on page 6. In addition, assign all 1 peaks to the corresponding nuclei. 6

5 Name Key 215 W13-Exam No. 1 Page 6 VI. (continued) 13 C NMR spectrum in CDCl 3 (1) (1 points) What is (are) the unit(s) of unsaturation of this compound? one! (2) (2 point) What does the IR spectral information tell you in terms of the presence of an -containing functional group in this molecule? (3) (2 points) What do the 13 C NMR spectral data tell you in terms of the presence of an -containing functional group in this molecule? carbonyl group ester group () ( points) What is the structure of the (5) (6 points) Draw in the box below the structure compound? (no partial) you drew in () and assign all 1 peaks and the 13 C peak at 6.38 ppm to the corresponding nuclei in the proposed structure ppm.0 ppm 0.9 ppm 3 C C ppm 1.6 ppm 6.38 ppm 1 pt for each chem shift assignment 6

6 Name Key 215 W13-Exam No. 1 Page 7 VII. (8 points) For each of the following reactions, draw in the box provided the structure of the expected major product. (1) 1. AlCl 3 Cl work-up (2) 1. Cs 2 C 3 C 3 C 2 -I 50 C, DMF work-up C 2 C 3 VIII. (9 points) The 1 NMR data for and 5 of diol 5 are shown below. Please note that two hydroxy s are not involved with 1 1 couplings. δ 3.88 ppm (dd, J = 3. and 2.5 z) δ 3.72 ppm (dd, J = 12.0 and 3. z) Si C 3 C Si (1) n the basis of the NMR data above, show the stereochemistry of alcohol 5 at C- and C-5 by writing in the boxes above right s and s (6 points). (2) Indicate below the coupling constants for each of the following (3 points): 3 J 3, = 12.0 z; 3 J,5 = 3. z; 3 J 5,6 = 2.5 z

216 W10-Exam #1 Page 1 of 9. I. (8 points) 1) Given below are infrared (IR) spectra of four compounds. The structures of compounds are given below. Assign each spectrum to its compound by putting the letter

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