Organic Chemistry, Binder Ready Version
Organic Chemistry, Binder Ready Version
2nd Edition
ISBN: 9781118454312
Author: David R. Klein
Publisher: WILEY
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Chapter 3.3, Problem 9ATS

a)

Interpretation Introduction

Interpretation: The nature of lone pair present on Nitrogen and Oxygen atom has to be identified.

Concept Introduction:

There are two ways to identify the acidity of the compounds,

  1. 1) Via comparing pKa values of the given compounds (quantitative approach)
  2. 2) Via study the structures of the acid (qualitative approach)

However, herein we consider only comparing pKa values.

PKa Value: The pKa value computes the acidity of an acid. This value depends upon the chemical property and identity of the compound.

            pKa = - log Ka

Where,

Ka is the measure of strength of an acid. If the acid is strong means Ka on the order of 1010 and weak means Ka on the order of 1050. Strong acid means pKa value is low value and Weak acid means pKa value is high.

To identify: which of the two lone pair are more basic

b)

Interpretation Introduction

Interpretation: The nature of lone pair present on Nitrogen and Oxygen atom has to be identified.

Concept Introduction:

There are two ways to identify the acidity of the compounds,

  1. 1) Via comparing pKa values of the given compounds (quantitative approach)
  2. 2) Via study the structures of the acid (qualitative approach)

However, herein we consider only comparing pKa values.

PKa Value: The pKa value computes the acidity of an acid. This value depends upon the chemical property and identity of the compound.

            pKa = - log Ka

Where,

Ka is the measure of strength of an acid. If the acid is strong means Ka on the order of 1010 and weak means Ka on the order of 1050. Strong acid means pKa value is low value and Weak acid means pKa value is high.

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Part I. a) Elucidate the structure of compound A using the following information. • mass spectrum: m+ = 102, m/2=57 312=29 • IR spectrum: 1002.5 % TRANSMITTANCE Ngg 50 40 30 20 90 80 70 60 MICRONS 5 8 9 10 12 13 14 15 16 19 1740 cm M 10 0 4000 3600 3200 2800 2400 2000 1800 1600 13 • CNMR 'H -NMR Peak 8 ppm (H) Integration multiplicity a 1.5 (3H) triplet b 1.3 1.5 (3H) triplet C 2.3 1 (2H) quartet d 4.1 1 (2H) quartet & ppm (c) 10 15 28 60 177 (C=0) b) Elucidate the structure of compound B using the following information 13C/DEPT NMR 150.9 MHz IIL 1400 WAVENUMBERS (CM-1) DEPT-90 DEPT-135 85 80 75 70 65 60 55 50 45 40 35 30 25 20 ppm 1200 1000 800 600 400
• Part II. a) Elucidate The structure of compound c w/ molecular formula C10 11202 and the following data below: • IR spectra % TRANSMITTANCE 1002.5 90 80 70 60 50 40 30 20 10 0 4000 3600 3200 2800 2400 2000 1800 1600 • Information from 'HAMR MICRONS 8 9 10 11 14 15 16 19 25 1400 WAVENUMBERS (CM-1) 1200 1000 800 600 400 peak 8 ppm Integration multiplicity a 2.1 1.5 (3H) Singlet b 3.6 1 (2H) singlet с 3.8 1.5 (3H) Singlet d 6.8 1(2H) doublet 7.1 1(2H) doublet Information from 13C-nmR Normal carbon 29ppm Dept 135 Dept -90 + NO peak NO peak 50 ppm 55 ppm + NO peak 114 ppm t 126 ppm No peak NO peak 130 ppm t + 159 ppm No peak NO peak 207 ppm по реак NO peak
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