Pushing Electrons
4th Edition
ISBN: 9781133951889
Author: Weeks, Daniel P.
Publisher: Cengage Learning
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Chapter 2, Problem 21EQ
Interpretation Introduction
Interpretation:
The resonance structure of the given molecule is to be determined
Concept Introduction:
When the electron distribution of a molecule can be depicted correctly in more than one way using different Lewis structures, the drawings are called resonance structures.
Resonance structures have no discrete existence of their own but, taken in combination, describe the true structure of the molecule.
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The structure of Vitamin C (ascorbic acid) is shown below. As the name indicates, the molecule is somewhat acidic. Actually, one of the hydrogens on the four OH groups is much more acidic than the other three ones. Which one is the acidic hydrogen?
Hints: To find the answer, you will again have to draw some resonance structures of the product formed after loss of H+. Consider the product after the loss of H+ for each of the OH groups. Only two of the OH groups have resonance structures after deprotonation; one of these two groups has a much better resonance structure than the other one (again after deprotonation). Note that the oxygen atom that is part of the five-membered ring has nothing to do with the problem.
Answer this question:
Based on the results of the solubility tests and chemical tests, what is the most probable structure of C6H5C3H5O? Draw your answer in the box You may draw the compound usingline-bond formula OR Lewis structure.
Problem statement:You were tasked to propose a structure for a compound with a chemical formula of C6H5C3H5O. In the laboratory, the compound appears as a clear, colorless liquid.
See table 1, for the results of solubility tests for C6H5C3H5O.
Table 1. Results of the solubility tests for C6H5C3H5O.
SOLUBILITY TEST
OBSERVATIONS
+(soluble/miscible)/
- (insoluble)
distilled water
two layers of liquid
-
10% NaHCO3
two layers of liquid
-
10% NaOH
two layers of liquid
-
10% HCl
two layers of liquid
-
concentrated H2SO4
pinkish solution
+
Based on the results of the solubility tests, the compound can be grouped in VI, which is insoluble in water, 10% NaOH and 10% HCl but soluble in concentrated H2SO4.
If the…
Chapter 2 Solutions
Pushing Electrons
Ch. 2 - One Lewis structure for the 2-butenyl cation is...Ch. 2 - Prob. 2EQCh. 2 - One structure for the conjugate acid of acetone...Ch. 2 - Similarly, a resonance structure for the conjugate...Ch. 2 - Prob. 5EQCh. 2 - Pairs of unshared electrons can be pushed. One...Ch. 2 - One structure for the acetoxonium ion is Clearly,...Ch. 2 - Prob. 8EQCh. 2 - There are no important resonance structures for...Ch. 2 - Prob. 10EQ
Ch. 2 - Prob. 11EQCh. 2 - Prob. 12EQCh. 2 - Prob. 13EQCh. 2 - Prob. 14EQCh. 2 - Prob. 15EQCh. 2 - Prob. 16EQCh. 2 - Prob. 17EQCh. 2 - The cyclohexane carboxylate anion has a Lewis...Ch. 2 - One Lewis structure for the enolate anion of...Ch. 2 - Prob. 20EQCh. 2 - Prob. 21EQCh. 2 - Prob. 22EQCh. 2 - Prob. 23EQCh. 2 - Prob. 24EQCh. 2 - Prob. 25EQCh. 2 - Prob. 26EQCh. 2 - Prob. 27EQCh. 2 - Prob. 28EQ
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