Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 16, Problem 16.59AP
Interpretation Introduction

(a)

Interpretation:

The compound A from its spectroscopic data is to be identified.

Concept introduction:

In mass spectroscopy, compounds can be identified on the basis of mass of compound. When the compound breaks into fragment then they can be distinguished from the other compounds. This technique is also used to differentiate the isotopes of compounds. This technique did not interact with electromagnetic radiation. Two peaks are used to identify the compound, first, the molecular ion peak which is the mass of the compound and second, the base peak which is the most abundant element peak. It may be same or different.

Interpretation Introduction

(b)

Interpretation:

The compound B with molecular formula C10H12O from its spectroscopic data is to be identified.

Concept introduction:

NMR spectroscopy is a technique used to determine a unique structure of the compounds. It identifies the carbon-hydrogen bonding of an organic compound. A hydrogen atom is called as a proton in the NMR spectroscopy.

The number of NMR signal in a compound is equal to the number of chemically non-equivalent protons present in that compound. The more the shielded proton less will be its chemical shift value and the corresponding signal will be produced at the right-hand side or lower frequency region or vice versa.

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The 'H NMR spectrum of compound A (C3H100) has four signals: a multiplet at 8 = 7.25-7.32 ppm (5 H), a singlet at d = 5.17 ppm (1 H), a quartet at d = 4.98 ppm (1 H), and a doublet at ô = 1.49 ppm (3 H). There are 6 signals in its 13C NMR spectrum. The IR spectrum has a broad absorption in the -3200 cm-1 region. Compound A reacts with KMNO4 in a basic solution followed by acidification to give compound B with the molecular formula C7H6O2. Draw structures for compounds A and B.
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This is the 13C spectrum for an X compound with molecular formula C7H12O4. The substance is not soluble in NaHCO3 and has a stretch at 1740cm-1 on the IR spectrum. What is the structure of X?

Chapter 16 Solutions

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