Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 19, Problem 19.72AP
Interpretation Introduction

Interpretation:

A suitable structure for compound A having the molecular formular C6H12O3 that is in accordance with the given spectroscopic data is to be stated.

Concept introduction:

Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. IR spectroscopy is used for the detection of functional group present in the compound. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

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An aromatic compound K, whose molecular formula is C8H11N, is examined in the laboratory to elucidate its structure. The following observations were made: A) Compound K is soluble in dilute hydrochloric acid but insoluble in sodium hydroxide solution. B) Treatment of compound K with excess potassium hydroxide and benzenesulfonyl chloride, C(6)H(5)SO(2)Cl, results in the formation of a heterogeneous mixture. The NMR spectrum of compound K is shown below. C) Compound K when treated with acetic anhydride[CH3-C(O)-O-C(O)-CH3], gives compound L, whose molecular formula is C(10)H(13)ON. Compound L is insoluble in dilute acid or dilute base at room temperature, heating compound L in dilute acid or base, however, regenerates compound K. D) When compound L is heated with a mixture of concentrated nitric acid and sulfuric acid, a single product, compound M, with the molecular formula C(10)H(12)O(3)N(2) is formed in excellent yields. On the basis of these observations draw the structures of…
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