12) infrared spectra and 1H NMR spectra for each compound are provided on this and the next Compounds A, B, and C were found to have a molecular formula CaHsO2. The page. Determine the structural formula of each compound. IHD = Compound A 6 H Compound A 1 H 1 H 11 10 Compound B 3 H Compound B 1H Kexchanges with D20) 2H 10 Compound C ff 口 Compound C 3H 1 H 2H 2 H 10

With reference to structure A, label structure B as an identical compound, a constitutional isomer, a resonance structure, or none of the above. Select the single best answer.

Q4: The proton NMR spectrum of a compound with formula C8H14O2 is shown. The DEPT experimental results are tabulated. The infrared spectrum shows medium-sized bands at 3055, 2960, 2875, and 1660 cm-1 and strong bands at 1725 and 1185 cm-1. Draw the structure of this compound. Normal Carbon DEPT-135 DEPT-90 10.53 ppm Positive No peak Positive No peak No peak No peak 12.03 14.30 Positive 22.14 Negative No peak No peak 65.98 Negative 128.83 No peak 136.73 Positive Positive 168.16 No peak No peak (C=0) 0.97 2.05 7.92 2.96 7.0 6.5 60 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0

Give the compounds with the following spectral data. a. C8H8O3 IR: 3500 cm to 2500 cm, 1688 cm! NMR: 8 3.8, s, 3H 87.0, d, 2H 8 7.9, d, 2H 8 12.7, s, 1H b. CSH1002 IR: 3400 cm to 2600 cm, 1701 cm NMR: 8 0.9, s, 3H 8 1.6, m, 2H 8 2.0, d, 3H 82.9, m 1H 8 11.7, s, 1H

Question 12

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Q3: The proton NMR spectrum of a compound with formula C5H100 is shown. The DEPT experimental results are tabulated. The infrared spectrum shows medium-sized bands at 2968, 2937, 2880, 2811, and 2711 cm1 and strong bands at 1728 cm-1. Draw the structure of this compound. Normal Carbon DEPT-135 DEPT-90 11.35 ppm No peak No peak No peak Positive 12.88 Positive 23.55 Negative 47.78 Positive Positive 205.28 Positive Positive (C=0) T m 240 2.35 2.30 2.25 2.20 0.75 0.91 1.04 1.01 2.90 2.92 9.6 9'5 24 23 2.2 2.1 2.0 1.9 1.8 1.7 1.6 14 1.3 1.2 1.1 10 0.9 2890.2 \ 2888.0 690.2 0'889 F189¬ 669.6 667.8

Please sol;;;!!!!:??

PART 2: NMR SPECTRA #1: C4H,Cl- no important IR peaks are seen. 3.5 2H 3.0 possible structure 2.5 300 MHz 'H NMR In CDC3 2.0 it wa 1.5 2H 2H 1.0 3H 0.5 0.0

3. Compound A (C,H,0) can be reduced to compound B (C,Hg0) with LIA1H. The nmr spectrum of compound B is given below. Write structures for compounds A and B. A (3 HGO) Li Al Hy. + £ दHzo) 200 200 00 TMS