Organic Chemistry
Organic Chemistry
3rd Edition
ISBN: 9781119338352
Author: Klein
Publisher: WILEY
Question
Book Icon
Chapter 22, Problem 89IP
Interpretation Introduction

Interpretation: The stronger basic character of guanidine compared to other amines has to be found

Concept Introduction:

Resonance is a mental exercise and method within the Valence Bond Theory of bonding that describes the delocalization of electrons within molecules.  The net sum of valid resonance structures is defined as a resonance hybrid, which represents the overall delocalization of electrons within the molecule.  A molecule that has several resonance structures is more stable than one with fewer.  If a compound has high resonance structures and the lone pair on any other atom is delocalized, then that compound is less basic.  If a compound has no resonance structures and the lone pair on any other atom is localized, then that compound is more basic.

To find: Explain the stronger basic character of guanidine compared to other amines

Find the nitrogen atom which is protonated easily in guanidine

Organic Chemistry, Chapter 22, Problem 89IP

Blurred answer
Students have asked these similar questions
The acid-base chemistry of both EDTA and EBT are important to ensuring that the reactions proceed as desired, thus the pH is controlled using a buffer. What percent of the EBT indicator will be in the desired HIn2- state at pH = 10.5. pKa1 = 6.2 and pKa2 = 11.6 of EBT
What does the phrase 'fit for purpose' mean in relation to analytical chemistry? Please provide examples too.
For each of the substituted benzene molecules below, determine the inductive and resonance effects the substituent will have on the benzene ring, as well as the overall electron-density of the ring compared to unsubstituted benzene. Molecule Inductive Effects Resonance Effects Overall Electron-Density × NO2 ○ donating O donating O withdrawing O withdrawing O electron-rich electron-deficient no inductive effects O no resonance effects O similar to benzene E [ CI O donating withdrawing O no inductive effects Explanation Check ○ donating withdrawing no resonance effects electron-rich electron-deficient O similar to benzene © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center Acces

Chapter 22 Solutions

Organic Chemistry

Ch. 22.4 - Prob. 10CCCh. 22.4 - Prob. 11CCCh. 22.5 - Prob. 2LTSCh. 22.5 - Prob. 12PTSCh. 22.5 - Prob. 13ATSCh. 22.6 - Prob. 3LTSCh. 22.6 - Prob. 14PTSCh. 22.6 - Prob. 15ATSCh. 22.7 - Prob. 4LTSCh. 22.7 - Prob. 16PTSCh. 22.7 - Prob. 17PTSCh. 22.7 - Prob. 18PTSCh. 22.7 - Prob. 19ATSCh. 22.8 - Prob. 20CCCh. 22.8 - Prob. 21CCCh. 22.8 - Prob. 22CCCh. 22.9 - Prob. 5LTSCh. 22.9 - Prob. 23PTSCh. 22.9 - Prob. 24ATSCh. 22.10 - Prob. 25CCCh. 22.11 - Prob. 26CCCh. 22.11 - Prob. 6LTSCh. 22.11 - Prob. 27PTSCh. 22.11 - Prob. 28ATSCh. 22.12 - Prob. 29CCCh. 22.12 - Prob. 30CCCh. 22.13 - Prob. 31CCCh. 22.13 - Prob. 32CCCh. 22 - Prob. 33PPCh. 22 - Prob. 34PPCh. 22 - Prob. 35PPCh. 22 - Prob. 36PPCh. 22 - Prob. 37PPCh. 22 - Prob. 38PPCh. 22 - Prob. 39PPCh. 22 - Prob. 40PPCh. 22 - Prob. 41PPCh. 22 - Prob. 42PPCh. 22 - Prob. 43PPCh. 22 - Prob. 44PPCh. 22 - Prob. 45PPCh. 22 - Prob. 46PPCh. 22 - Prob. 47PPCh. 22 - Prob. 48PPCh. 22 - Prob. 49PPCh. 22 - Prob. 50PPCh. 22 - Prob. 51PPCh. 22 - Prob. 52PPCh. 22 - Prob. 53PPCh. 22 - Prob. 54PPCh. 22 - Prob. 55PPCh. 22 - Prob. 56PPCh. 22 - Prob. 57PPCh. 22 - Prob. 58PPCh. 22 - Prob. 59PPCh. 22 - Prob. 60PPCh. 22 - Prob. 61PPCh. 22 - Prob. 62PPCh. 22 - Prob. 63PPCh. 22 - Prob. 64PPCh. 22 - Prob. 65PPCh. 22 - Prob. 66PPCh. 22 - Prob. 67PPCh. 22 - Prob. 68PPCh. 22 - Prob. 69PPCh. 22 - Prob. 70PPCh. 22 - Prob. 71PPCh. 22 - Prob. 72PPCh. 22 - Prob. 73IPCh. 22 - Prob. 74IPCh. 22 - Prob. 75IPCh. 22 - Prob. 76IPCh. 22 - Prob. 77IPCh. 22 - Prob. 78IPCh. 22 - Prob. 79IPCh. 22 - Prob. 80IPCh. 22 - Prob. 81IPCh. 22 - Prob. 82IPCh. 22 - Prob. 83IPCh. 22 - Prob. 84IPCh. 22 - Prob. 85IPCh. 22 - Prob. 86IPCh. 22 - Prob. 87IPCh. 22 - Prob. 88IPCh. 22 - Prob. 89IPCh. 22 - Prob. 90IPCh. 22 - Prob. 91IPCh. 22 - Prob. 92IPCh. 22 - Prob. 93IPCh. 22 - Prob. 94IPCh. 22 - Prob. 95IPCh. 22 - Prob. 96CPCh. 22 - Prob. 97CPCh. 22 - Prob. 98CPCh. 22 - Prob. 99CP
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY