ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL
ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL
8th Edition
ISBN: 9780134595450
Author: Bruice
Publisher: PEARSON
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Chapter 20.5, Problem 10P
Interpretation Introduction

Interpretation:

The mechanism for the base-catalyzed conversion of D-fructose to D-glucose and D-mannose has to be written.

Concept Introduction:

In the conversion of D-fructose to D-glucose the base is required as a catalyst.  Therefore, such reactions are called base catalyzed reactions.  The base first removes a proton from carbon position 1 and forms an enolate ion.  The enolate ion is further protonated by the other proton.  That proton comes from the top or from the bottom of the planar sp2-hybridized carbon.

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Part II. Given two isomers: 2-methylpentane (A) and 2,2-dimethyl butane (B) answer the following: (a) match structures of isomers given their mass spectra below (spectra A and spectra B) (b) Draw the fragments given the following prominent peaks from each spectrum: Spectra A m/2 =43 and 1/2-57 spectra B m/2 = 43 (c) why is 1/2=57 peak in spectrum A more intense compared to the same peak in spectrum B. Relative abundance Relative abundance 100 A 50 29 29 0 10 -0 -0 100 B 50 720 30 41 43 57 71 4-0 40 50 60 70 m/z 43 57 8-0 m/z = 86 M 90 100 71 m/z = 86 M -O 0 10 20 30 40 50 60 70 80 -88 m/z 90 100
Part IV. C6H5 CH2CH2OH is an aromatic compound which was subjected to Electron Ionization - mass spectrometry (El-MS) analysis. Prominent m/2 values: m/2 = 104 and m/2 = 9) was obtained. Draw the structures of these fragments.
For each reaction shown below follow the curved arrows to complete each equationby showing the structure of the products. Identify the acid, the base, the conjugated acid andconjugated base. Consutl the pKa table  and choose the direciton theequilibrium goes. However show the curved arrows. Please explain if possible.

Chapter 20 Solutions

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL

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