Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 19, Problem 19.10P
Interpretation Introduction

(a)

Interpretation:

The explanation for the fact that the m/z=57 fragment peak is much more intense in the spectrum of 3, 3-dimethyl-2-butanone than it is in the spectrum of 2-hexanone is to be stated.

Concept introduction:

Spectroscopy method is used to identify the structure of the substance. The mass spectroscopy is used to determine the molecular mass of a compound. In the mass spectrum, the molecular ion peak is the most important peak. The ratio m/z of the molecular ion occurs at the molecular mass.

Interpretation Introduction

(b)

Interpretation:

The explanation for the fact that the spectrum of 3, 3-dimethyl-2-butanone (B) does not shows a fragment at m/z=58, but that of 2-hexanone shows is to be stated.

Concept introduction:

Spectroscopy method is used to identify the structure of the substance. The mass spectroscopy is used to determine the molecular mass of a compound. In the mass spectrum, the molecular ion peak is the most important peak. The ratio m/z of the molecular ion occurs at the molecular mass.

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1 (c) 2-Methyl-3-pentanol reacts with PCC to form compound F. (i) Draw the structure of F. (ii) In the mass spectrum, identify the m/z value of the molecular ion peak for compound F. (ii) Fragmentation of radical cation F exhibits two fragment ion peaks at m/z 57 and m/z 71. Propose the structures of these two fragments. (iv) Draw the resonance structure for each of the cation in (iii).
How could 1H NMR spectroscopy be used to distinguish among isomers A, B, and C?
2 (a) In the following reaction, PCC A (i) Draw the structure of compound A. (ii) Explain using the IR spectra to confirm that the reaction is completed. (iii) Identify the molecular ion peak for compound A. (iv) Fragmentation of A shows a peak at m/z 111. Draw the possible cation for this peak. (v) Determine the resonance structure of this cation.

Chapter 19 Solutions

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