ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
10th Edition
ISBN: 9781259972348
Author: Carey
Publisher: MCG CUSTOM
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Chapter 24, Problem 48DSP
Interpretation Introduction

Interpretation:

Correct structures for the hexose that gives the same aldaric acid as (+)-glucose is to be chosen.

Concept introduction:

The stereoisomers that are not mirror images are diastereomers.

They differ in absolute configuration at only one chirality center.

(+)-glucose and its diasteromeric hexose undergo oxidation at C-1 and C-6 carbon atoms to form optically active aldaric acid.

The aldaric acids have two -COOH groups at both ends of the carbon chain. There is no way to tell which was originally the -CHO and which was -CH2OH, and thus, a given aldaric acid can have two different precursors.

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Done 11:14 ⚫ worksheets.beyondlabz.com 5 (a). Using the peak information you listed in the tables for both structures, assign each peak to that portion of the structure that produces the peak in the NMR spectrum. Draw this diagram on your own sheet of paper and attach the sketch of your drawing to this question. Question 6 5 (b). Using the peak information you listed in the tables for both structures, assign each peak to that portion of the structure that produces the peak in the NMR spectrum. Draw this diagram on your own sheet of paper and attach the sketch of your drawing to this question. Question 7 6. Are there any differences between the spectra you obtained in Beyond Labz and the predicted spectra? If so, what were the differences? <
2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled** Peak Chemical Shift (d) 5.7 1 Multiplicity multiplate .......... 5.04 double of doublet 2 4.98 double of doublet 3 4.05 doublet of quartet 4 5 LO 3.80 quartet 1.3 doublet 6 Peak Chemical Shift (d) Multiplicity
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