Question

-7.5014 4.6768 6.4777 -2.2283 -7.2691 -7.1894 PROTON4 CDC13 (C:\Bruker\TopSpin3.2.6} tbennet6-ga 18 11.0124 -5.8727 10.3214 - 0.8901 2.1820 2.0980 -M 4.1648 -3.9851 - 3.8482 -3.6909 1.9890 0.2808 - 2.8186 -2.6720 10.2327 - 2.1722 -1.6993 0.8986 - 1.2790 3.0000 1.1290 1.0482 -0.8708 (ppm) " "" "","102 [rel trom

Having trouble analyzing this HNMR spectra for my ochem 2 lab. We did a Grignard reaction with fructone, 2 equivalents of phenylmagnesium bromide, ether, and NH₄Cl to create a tertiary alcohol (our product). Posting this H NMR spectra along with the reaction we did in this step of the synthesis. My main question is where on the spectra is my tertiary alcohol and how much of it do I have along with any other significant findings in this spectra. Thank you!

Answer 1

Grignard reaction with fructone worked and you are having your product more than 95%. There are some solvents peaks in your nmr data other than that compound is pure. I have attached nmr data here for your compound. I guess it is ethyl acetate peaks after workup.

ChemNMR 'H Estimation 7.22 7.31 / 7.31 7.46 / 7.487 7.46 7.31 >3.85;3.75 OR30 0 7.227 .4652 3.85;3.75 7.31 Estimation quality is indicated by color: good, medium, rough 130 ORO 0516:3.75 5 4 PPM 3 2 1 Protocol of the H-1 NMR Prediction (Lib=SU Solvent=DMSO 300 MHz): Node Shift Base + Inc. Comment (ppm rel. to TMS) OH 5.52 4.20 2.40 -1.08 3.90 CH2 3.85,3.750000 CH2 3.85,3.750000 CH 7.46 0 CH 7.46 CH 7.46 CH 7.46 CH 7.31 CH 7.31 -0.10 3.90 ? -0.10 7.26 0.00 0.20 7.26 0.00 0.20 7.26 0.00 0.20 7.26 0.00 0.20 7.26 0.03 0.02 7.26 0.03 0.02 7.26 0.03 0.02 7.26 0.03 0.02 7.26 -0.03 -0.01 7.26 -0.03 -0.01 1.37 0.26 -0.06 0.58 0.15 0.86 0.50 0.05 -0.14 alcohol 1 -C(C*R) C*R general corrections 1,3-dioxolan 2 unknown substituent (s) general corrections 1,3-dioxolan 2 unknown substituent (s) general corrections 1-benzene 1 -C-o general corrections 1-benzene 1 -C-0 general corrections 1-benzene 1 -C-0 general corrections 1-benzene 1 -C-o general corrections 1-benzene 1 -C-o general corrections 1-benzene 1 -C-o general corrections 1-benzene 1 -C-o general corrections 1-benzene 1 -C-0 general corrections 1-benzene 1 -C-o general corrections 1-benzene 1 -C-o general corrections methylene 2 beta -O-C 1 beta -C 2 beta -1:0*C*C*C*C*C*1 1 beta -O methyl 2 beta -O-C 1 beta -CC general corrections CH 7.31 CH 7.31 CH 7.22 CH 7.22 CH2 2.30 O O CH3 1.27 1H NMR Coupling Constant Prediction shift atom index coupling partner, constant and vector 5.52 3.80 10 19 diastereotopic -12.4 H-C-H 20 7.1 H-CH-CH-H 20 diastereotopic -12.4 H-C-H 19 7.1 H-CH-CH-H 3.80 7.46 7.5 1.5 1.5 H-C*C-H H-C*C*C-H H-C* CH*C-H 7.46 * * 7.5 1.5 1.5 H-C*C-H H-C*C*C-H H-CÁCH*C-H * 7.46 7.5 1.5 1.5 H-C*C-H H-C*C*C-H H-C*CH*C-H 7.46 * * 7.5 1.5 1.5 H-C*C-H H-C*C*C-H H-CÁCH*C-H * 7.31 7.5 7.5 1.5 H-C*C-H H-C*C-H H-CÁCH*C-H 7.31 H HHHHH * Ο FUNA O P W DWA WNO Nwi PNS WA NOW WUN NA. 7.5 7.5 1.5 H-C*C-H H-C*C-H H-C*CH*C-H * Ο * Ο 7.31 * * 7.5 7.5 1.5 H-C*C-H H-C*C-H H-C*CH*C-H * 7.31 12 * C * 7.5 7.5 1.5 H-C*C-H H-C*CH*C-H * 7.22 * 0 * Ο 0 1 4 7.5 7.5 1.5 1.5 H-C*C-H H-C*C-H H-C*CH*C-H H-C* CH*C-H * Ο 0 H HHHHHHHHHH * Ο 7.22 13 7.5 7.5 1.5 1.5 H-C*C-H H-C*C-H H-CÁCH*C-H H-C* CH*C-H * * Ooo OOO * * 2.30 1.27