IR, C and DEPT NMR, H NMR, HETCOR correlations, HMBC correlations, COSY correlat

Question

IR, C and DEPT NMR, H NMR, HETCOR correlations, HMBC correlations, COSY correlations.

Please perdict a structure using the following spectra and be as elaborate as possible.The molar mass of the compound is 316! Please elaborate on each spectra. Thanks!

The molar mass of the compound is 316

C and DEPT NMR carbons: 187, 172, 151, 146, 135, 134, 130, 127, 118, 114, 75, 58, 52, 39, 38, 19, 17, 13

IR:

H NMR:

C and DEPT NMR:

HETCOR correlations:

COSY correlations:

HMBC correlations:

Chem 318319 Beauchamp Name- Problem 70 Predict a reasonable structure from the spectral information provided below. As much as possib match the spectral information to the part of the structure that it explains. Show all of your work. IR Spectrum: Interpret as fully as possible from structure. Not every peak is interpretable. (units cm MS data exact mass Exact Mass: 316.18 1630 M+ 316, 18 (100.0%), 1380 M+1 317-18 20.6%), 3030 M 2-318.19 (1.9%) so 1700 1660 1470 1230 2960-2850 4000 3500 3000 2500 2000 Proton NMR: interpret data (calculate chemical shifts to confirm they match actual values, N neighbors) 2.85 3H, s 1H,brd s 6.79 7.36 3.69

Explanation / Answer

Mass is Even ; Therefore No nitrogen present . ( According to Nitrogen Rule)

Percent Abundance tells that There are 19 Carbons present ( Abundance of Carbon in M+1 peak is 1.08)

IR spectra Shows a sharp peak in the range of 2500-3000 indicating presence of Aromatic Proton

Peak in the region of 3400 Confirms the presence of Alcohol.

IR spectra in the range of 750- 850 and in 1 H Nmr specta Chemical shift in the range of 7-8 ppm and in 13 C Nmr spectra Tells aromatic proton.

Cosy Tells about the similar Nature of protons.

Hence the formula would be C19H24O4.DBE (8)

And the Structure would consist of a naphthalene ring with a ketone (IR 1690) and alcohol group.

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