Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
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Chapter 21, Problem 21.20P

(a)

Interpretation Introduction

Interpretation:

With the help of given mass values, infrared and 1H NMR spectrums, structural formula of compound Chas to be deduced.

Concept Introduction:

Mass spectrum: It generates multiple ions from the sample under investigation, it than separates them according to their specific mass to charge ration (m/z) and records the relative abundance (RA) of each ion types.

    MelectronbeamM+.+e-[Molecule]Molecular ionelectron[Radicalcation]

The 1H NMR spectrum of a compound provides some vital information that is required to predict the structure of the compound.  The chemical shift values can predict the groups that are present in the molecule.  The splitting of signals by the (N+1) rule predicts the number of hydrogens or protons attached to the adjacent carbon in a carbon chain of a compound.  Withthis information, the structure of the compound can be predicted.

IR Spectrum: It is concerned with the study of absorption of infrared, which causes vibration transition in the molecule. It is mainly used to identify functional groups present in molecules.

(b)

Interpretation Introduction

Interpretation:

The apperance of peaks in the mass spectrum of compound C at the given m/z values has to be accounted.

Concept introduction:

Basic principle of mass spectrum: It generates multiple ions from the sample under investigation, it than separates them according to their specific mass to charge ration (m/z) and records the relative abundance (RA) of each ion types.

    MelectronbeamM+.+e-[Molecule]Molecular ionelectron[Radicalcation]

Alphaα cleavage: This cleavage in mass spectrometry is a characteristic fragmentation of the molecular ion derived from carbonyl compound, in which the bond linking the carbonyl carbon to the atom occupying an alpha position breaks.

It is an expected pathway for carbonyl compounds, ethers, halide, alcohols and amines.

Organic Chemistry, Chapter 21, Problem 21.20P

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Chapter 21 Solutions

Organic Chemistry

Ch. 21 - Name the following compounds and ions.Ch. 21 - Prob. 21.9PCh. 21 - Draw a structural formula for each compound. (a)...Ch. 21 - Molecules of 6,6-dinitrobiphenyl-2,2-dicarboxylic...Ch. 21 - Following each name is the number of Kekul...Ch. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Prob. 21.15PCh. 21 - Which of the molecules and ions given in Problem...Ch. 21 - Prob. 21.17PCh. 21 - Naphthalene and azulene are constitutional isomers...Ch. 21 - Prob. 21.19PCh. 21 - Prob. 21.20PCh. 21 - Following are IR and 1H-NMR spectra of compound D....Ch. 21 - Compound E (C8H10O2) is a neutral solid. Its mass...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Compound H (C8H6O3) gives a precipitate when...Ch. 21 - Compound I (C11H14O2) is insoluble in water,...Ch. 21 - Propose a structural formula for compound J...Ch. 21 - Propose a structural formula for the analgesic...Ch. 21 - Prob. 21.29PCh. 21 - Prob. 21.30PCh. 21 - Given here are 1H-NMR and 13C-NMR spectral data...Ch. 21 - Prob. 21.32PCh. 21 - Prob. 21.33PCh. 21 - Prob. 21.34PCh. 21 - Arrange the molecules and ions in each set in...Ch. 21 - Prob. 21.36PCh. 21 - Prob. 21.37PCh. 21 - From each pair, select the stronger base.Ch. 21 - Prob. 21.39PCh. 21 - Prob. 21.40PCh. 21 - Prob. 21.41PCh. 21 - Prob. 21.42PCh. 21 - Following is an equation for iodination of...Ch. 21 - Prob. 21.44PCh. 21 - Prob. 21.45PCh. 21 - Prob. 21.46PCh. 21 - When warmed in dilute sulfuric acid,...Ch. 21 - In the chemical synthesis of DNA and RNA, hydroxyl...Ch. 21 - Prob. 21.49PCh. 21 - Write the products of the following sequences of...Ch. 21 - Prob. 21.51PCh. 21 - Show how to convert 1-phenylpropane into the...Ch. 21 - Prob. 21.53PCh. 21 - Cromolyn sodium, developed in the 1960s, has been...Ch. 21 - Prob. 21.55PCh. 21 - Prob. 21.56PCh. 21 - Prob. 21.57PCh. 21 - Prob. 21.58PCh. 21 - Prob. 21.59PCh. 21 - Prob. 21.60PCh. 21 - Prob. 21.61PCh. 21 - Prob. 21.62PCh. 21 - Prob. 21.63PCh. 21 - Following is a synthesis for toremifene, a...
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