ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
9th Edition
ISBN: 9780134645704
Author: WADE AND SIMEK
Publisher: PEARSON
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Chapter 12.15C, Problem 12.11P
Interpretation Introduction

Interpretation: The peaks at m/z87,111 and 126 in the mass spectrum of 2,6dimethylheptane4ol are to be accounted.

Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives us the information about the molecular formula as well.

Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak having an even mass number corresponding to loss of an even mass number.

To determine: The peaks at m/z87,111 and 126 in the mass spectrum of 2,6dimethylheptane4ol.

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1. For an unknown compound with a molecular formula of C8H100: a. What is the DU? (show your work) b. Solve the structure and assign each of the following spectra. 8 6 2 ō (ppm) 4 2 0 200 150 100 50 ō (ppm) LOD D 4000 3000 2000 1500 1000 500 HAVENUMBERI -11
16. The proton NMR spectral information shown in this problem is for a compound with formula CioH,N. Expansions are shown for the region from 8.7 to 7.0 ppm. The normal carbon-13 spec- tral results, including DEPT-135 and DEPT-90 results, are tabulated: 7 J Normal Carbon DEPT-135 DEPT-90 19 ppm Positive No peak 122 Positive Positive cus и 124 Positive Positive 126 Positive Positive 128 No peak No peak 4° 129 Positive Positive 130 Positive Positive (144 No peak No peak 148 No peak No peak 150 Positive Positive してし
3. Propose a synthesis for the following transformation. Do not draw an arrow-pushing mechanism below, but make sure to draw the product of each proposed step (3 points). + En CN CN
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