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'kk - 1 2 3 4 5 6 7 8 PPM doublet int = 2H doublet int = 2H...

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Chem 334 honors Challenge Problem 2 due Tuesday Feb 14 th 9:30 am. Michael characterized an unknown compound A , with molecular formula C 4 H 8 O, using 1H NMR, see below. Compound A gave a positive Tollens test. A was reacted with Wittig reagent shown and after an aqueous workup, Michael isolated a new compound B . Hydrogenation of B in ethanol gave a new compound C , which displayed an NMR spectra shown on the next page. Draw the structures of each compound ( A-C) and explain your answer using the spectral experimental and spectroscopic clues given. A PPh 3 THF B C H 2 / Pd H 3 C Proton NMR of compound A: 0 2 4 6 8 10 PPM doublet int = 1H multiplet int. = 1 H doublet int. = 6 H 1. Assign the Structure of compound A: Analysis of 1H NMR spectra: Type of H shift (ppm) integration splitting tentative identification Proton NMR of compound B: integration numbers given.
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Unformatted text preview: 1 2 3 4 5 6 7 8 PPM doublet int = 2H doublet int = 2H doublet int = 1H quartet (can you guess why?) int = 1H multiplet int = 1H singlet int = 3H doublet int = 6H 2. Assign the Structure of compound B: Analysis of 1H NMR spectra: Type of H shift (ppm) integration splitting tentative identification Proton NMR Spectra for Compound C. 1 2 3 4 5 6 7 8 PPM doublet int = 2H doublet int = 2H singlet int = 3H triplet int = 2H multiplet int = 3 H doublet int = 6H 3. Assign the Structure of compound C: Analysis of 1H NMR spectra: Type of H shift (ppm) integration splitting tentative identification 4. Draw the mechanism for the following reaction (use arrows to show the movement of electrons) show all lone pair and all major resonance structures. cat. HCl H 2 O H 3 C-O O-CH 3 O H O CH 3 2...
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