Question

b. Assign the indicated protons (a, b,c,d) in the Wittig product H NMR (CDC13, 60 MHz), (1 point) - W Ha 0 Hz YO Aromatic protons V Hb Hd US Z-40 SITI SCE - 43100 81257 72273 _-78728 -87449 We www WwWY www 60 0 55 50 45 Chemical Shutt pom) 50 c. Calculate two coupling constants. One for Ha and one for Hb of the Wittig product. If you need help, watch the Garcia mini lecture video that was posted on Friday, March 20th. What do these coupling constants tell us? (0.75 point) Focus F E

Answer 1

Hi there, i am so sorry for part-b, since this require Garcia mini lecture video posted on Friday March 20th on your university website, which is inaccessible for me. So i am gonna answer part-a now!

The given HNMR spectrum was complex and there is no further expanded spectral regions for me by you, hence i did a simulation on my lappy. The results are according to n+1 rule

8.1257 ppm, doublet, 1H due to Ha proton (due to coupling with adjacent Hb proton - 1+1 =2, doublet )

6.5295 ppm, doublet, 1H due to Hb proton (due to coupling with adjacent Ha proton - 1+1 =2, doublet )

4.32 ppm, quartet, 2H , due to Hc proton (due to coupling with adjacent Hd proton - 3+1 = 4, quartet)

1.3979 ppm, triplet, 3H, due to Hd proton (due to coupling with adjacent Hc proton - 2+1 = 3. triplet)

You may find coupling constants along with all other required relevant data in simulated HNMR spectrum below, and also attaching CNMR if incase you wanna compare this with your one!

Chemical structure with hydrogen exploded List of signals Assign... Delta Paste or drop a molfile or SMILES NbH Mult J (Hz) Zoo Drop or paste a jcamp file 23,36 7.11 Help O O i? Click to superimpose Nucl... Solvent Expe... Filen... O O II E* S 8 27,31 26,32 25,33 28,30 29 24,34,35 4.254 2 7.686 2 7.677 2 7.807 2 7.7535 2 8.577 1 1.1613 8.1011 dddd ddd ddt dddd quint コエース 7.90 6.98 1.40... 8.33 6.98 2.12 .33 1.40 0.45 7.90 2.69 2.12. 2.69 0.44 7.11 16.51 O O I O O I H OH d E TH NMR: 0 1.16 (3H, I, J = 7.1 Hz), 4.25 (2H, 9, J = 7.1 Hz), 6.64 (1H, d, J = 16.5 Hz), 7.63-7.84 (8H, 7.69 (dddd, J = 7.9, 7.0, 1.4, 0.4 Hz), 7.75 (dddd, J = 7.9, 2.7, 2.1, 0.5 Hzi 7.81 (ddt, J = 8.3, 1.4, 0.4 Hz), 7.68 (ddd, J = 8.3, 7.0, 2.1 Hz)), 8.10 (1H, d, J = 16.5 Hz), 8.58 (1H, tquint, J = 2.7, 0.4 Hz). /GOO+OZOLI OOOLŪeo- OBO 1H NMR spectra - Double click to zoom out, SHIFT + double click to zoom out by step, SHIFT + drag to move spectrum 10.05 ppm 1.0 1.b 8.0 Simulate spectrum Advanced options Frequency: 400 - From: 11 To: Line width: Number points: 32k ppm uppm Hz 10 - O (opm) predictedSpectrum Download all —

Molfile or SMILES Chemical structure with hydrogen exploded 6 (ppm) Paste or drop a molfile or SMILES Help 126.7 н 126.7 HHH OH 133.4 O Draw a chemical structure to predict NEw x R x = = ~AOOOOOOFG 0 II 167.3 128.9 コエイ 128.9 130.9 H OH I Drop or paste a jcamp file I 13C NMR spectra Calculate spectrum 120121 Draw a chemical structure and click on "Calculate spectrum". You may also DRAG / DROP a molfile You will get an interactive NMR spectrum. 200 150 100 0 (ppm)

Hope this helped you!

Thank You So Much!

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