Your Name: Question 1. Spectrum Prediction I: Ethyl Acetoacetate. (15 points) ppm ppm ppm ppm. J(A,D) = 8 Hz = 0.
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1 Question 1. Spectrum Prediction I: Ethyl Acetoacetate. (15 points) A B C D ppm ppm ppm ppm J(A,D) = 8 Hz = 0.08 ppm (in CDCl 3 ) Draw the 100 MHz H-NMR spectrum to scale. Draw splitting trees. C: Singlet at ppm with relative intensity 3 B: Singlet at ppm with relative intensity 2 A: Quartet (1:3:3:1, sum = 8) centered at 4.20 for 2H x 0.08 = 4.32 ppm with rel. intensity 0.25 (2 x 1/8) x 0.08 = 4.24 ppm with rel. intensity 0.75 (2 x 3/8) x 0.08 = 4.15 ppm with rel. intensity 0.75 (2 x 3/8) x 0.08 = 4.08 ppm with rel. intensity 0.25 (2 x 1/8) D: Triplet (1:2:1, sum = 4) centered at 1.29 for 3H x 0.08 = 1.37 ppm with rel. intensity 0.75 (3 x 1/4) 1.29 ppm with rel. intensity 1.50 (3 x 2/4) x 0.08 = 1.21 ppm with rel. intensity 0.75 (3 x 1/4) See SDBS #573 for spectrum (0.04 ml : 0.5 ml CDCl 3 ) -1-
2 Question 2. Spectrum Analysis I: Ethyl Acetoacetate. (15 points) (a) The CNMR spectrum shown above was recorded with a sample of higher concentration of ethyl acetoacetate in CDCl 3 (0.1 ml : 0.4 ml CDCl 3 ). Assign the peaks as best as possible. What compound causes the additional signals? Draw its structure and cite supporting evidence from Pretsch et al. Why does this compound only show up at higher concentration? (12 points) The concentration dependence suggests that intermolecular H-bonding is important for enolization. (b) The HNMR of the sample of higher concentration of ethyl acetoacetate (will, will not) be the same as the HNMR spectrum recorded in the same solvent at lower concentration. (3 points) -2-
3 Question 3. 2D-(H,C)-COSY Spectrum of Vinyl trans-crotonate, H 3 C-CH=CH-CO-O-CH=CH 2. (20 p.) Draw the expected heteronuclear 2D-COSY spectrum and adhere to the following rules: [1] H-NMR chemical shifts: A: 7.35, B: 7.11, C: 5.882, D: 4.909, E: 4.577, and F: ppm. [2] H-NMR on the horizontal axis; range: 0 10 ppm, chemical shift increases right-to-left. [3] C-NMR chemical shifts: (rel. int. 428) #1, (905) #2, (856) #3, (1000) #4, (910) #5, and (687) #6 (in CDCl 3 ). [4] C-NMR on vertical axis; range: ppm, chemical shift increases top-to-bottom. HNMR and CNMR: SDBS #
4 Question 4. Structure Analysis II: N-Acetylaminothiolactone. (20 points) (H,H)-COSY and (H,C)-COSY NMR spectra provided on the following page. Analyze the spectra (assign H and C, draw lines to off-diagonal peaks), circle the correct structure (following row) and explain how you made your selection (large box below). SDBS No.: ppm Int. Assign C(O)S C(O)N CH CH2-CH CH2-S Assign. Shift(ppm) A 6.01 B C* D* E* F G* There is a chiral C-atom. The chiral center causes non-equivalence of the H-atoms of the two methylene groups! The signals are not very strong in the 1D-HNMR spectra. But the signals are very clearly visible on the diagonal of the (H,H)-COSY! The CH-group s H-atom appears at 4.5 ppm -- Couples to (NH)-H! -- Couples to H-atoms of one methylene (G & E). ==> cannot be structure shown in center -- Distinguish between left and right structures based on chemical shifts Complete assignments are not required to determine the correct isomer. The (H,C)-COSY is provided as it helps to assign the Hs. -4-
5 -5-
6 Question 5. Structure Analysis III. Combination Problem, C 6 H 5 NO 2. (30 points) Formula, mass-, H- and C-NMR and two IR-spectra are provided. (a) Indicate pertinent observations directly in each spectrum and draw the correct structure on the right. (14 points) (b) Explain the fragmentation pattern in the box below (explain peaks with relative intensity > 40%). Clearly draw complete Lewis structures of the molecular ion and of all cations, radical cations, neutral radicals and/or neutral closed-shell systems that result by fragmentation. (12 p.) (c) On the last page: Describe and explain the significant differences observed in the IR spectra. (4 points) Structure (SDBS #7944) MS Fragmentation Pattern: Intensity > 40%: m/z = 123 = M + ; m/z = 105; m/z = 78 m/z = 78: = 45; lost CO 2 H, indicative of carboxylic acid. m/z = 106: = 17; possible loss of HO, NH 2. m/z = 105: = 18; possible loss of H 2 O, NH 3. Mass Spectrum, DIRECT, 75 ev -6-
7 HNMR, 400 MHz, g : 0.5 ml DMSO-d 6 CNMR, 90 MHz, g : 0.5 ml DMSO-d 6-7-
8 IR-Spectrum, Nujol Mull Significant Differences in IR Spectra: The peaks just below /cm are from nujol! Nujol is a mineral oil; alkanes. Otherwise, spectra are pretty much the same. Small difference in the peak just below /cm does not matter much. IR-Spectrum, KBr As part of (a), the expectations include three assignments: -- The IR range for the HO of a carboxylic acid is /cm. Nicotinic acid is on the low side. -- The IR range for the CO of an aromatic carboxylic acid is /cm. -- The broad band from 1800 to /cm: broad, overlapping aromatic overtones. -8-
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