ORGANIC CHEM +SG +SAPLING >IP<
ORGANIC CHEM +SG +SAPLING >IP<
6th Edition
ISBN: 9781319171179
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 20, Problem 20.60AP
Interpretation Introduction

Interpretation:

The structure of compound A is to be identified and two peaks in the mass spectrum are to be rationalized.

Concept Introduction:

In the IR spectroscopy, change in the dipole moment produces absorption of energy. All the functional groups have different absorption frequency based on which they can be differentiated. For carbonyl C=O group, the absorption takes place at 1725cm-1 which is different for carboxylic acid and esters. In proton NMR, the proton resonance is taken into consideration for different functional groups. Due to change in surroundings of the proton, the chemical shift changes.

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Part II. two unbranched ketone have molecular formulla (C8H100). El-ms showed that both of them have a molecular ion peak at m/2 =128. However ketone (A) has a fragment peak at m/2 = 99 and 72 while ketone (B) snowed a fragment peak at m/2 = 113 and 58. 9) Propose the most plausible structures for both ketones b) Explain how you arrived at your conclusion by drawing the Structures of the distinguishing fragments for each ketone, including their fragmentation mechanisms.
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