Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 5, Problem 12CTQ
Interpretation Introduction
Interpretation: The reason that explains zero possibility for resonance structure of following anion should be determined.
Concept introduction: Lewis structure is a representation of molecules in which dots are shown to represent unshared electrons and lines are shown to represent bonds. These lines and dots represent distribution of electrons in the molecule.
When one single structure is unable to describe all the properties of a single-molecule, a phenomenon called resonance comes into play. This arises when two or more than two Lewis structures are possible for one molecule. All such structures are called resonating structures and have same placement of atoms in them but these have different locations of bond pairs and lone pairs. The resonating structures are inter-convertible with each other. The resultant of all the resonating or contributing structures is called the resonance hybrid.
Rules to form resonance structure are as follows:
1. Use arrow types 1 and 2 for the resonance structure of anions in the movement of negative charge.
2. Use only arrow type 3 to move a positive charge for the resonance structure of cations.
3. The sigma bond should not be broken. Any atom must not move from its place and total number of electrons must be the same in all resonance structures.
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Draw three resonance structures for CS,. This species has its three atoms bonded sequentially in the following fashion: S-C-S.
Draw your resonance structures so that the atoms in them are bonded together in this order. Select the most important
resonance structure for this species based on the formal charges on the atoms of the three resonance structures you have
drawn. Select the choices from below which make the statements true about this (most important) resonance structure.
(a) The leftmost bond (between S and C) is a single
v bond.
(b) The rightmost bond (between C and S) is a single
v bond.
(c) The formal charge on the leftmost (S) atom is
-Select-v
(d) The formal charge on the central (C) atom is
-Select---v
(e) The formal charge on the rightmost (S) atom is
Select-v
(f) The number of nonbonding pairs (lone pairs) of electrons in the leftmost (S) atom is
Select-v pairs.
(g) The number of nonbonding (lone) pairs of electrons in the rightmost (S) atom is -Select-- v pairs.
Question
Provide each unique Lewis structure for the HONO molecule that maintains the H-O-NO connectivity and where all atoms have an octet (hydrogen a duet).
Your structures should explicitly show ALL bonds, all lone pairs, and all formal charges.
Which Lewis structure contributes more to the real hybrid structure of HONO?
What is the relationship between these Lewis structures and what type of arrow is used to show their relationship?
This question is confusing to me. Please explain your answer.
Are the bond lengths data consistent with a resonance model? Yes or no? Please explain thank you.
Chapter 5 Solutions
Organic Chemistry: A Guided Inquiry
Ch. 5 - Which elements on the periodic table (other than...Ch. 5 - You will not find “hydroxide” in the stockroom,...Ch. 5 - Prob. 3CTQCh. 5 - Prob. 4CTQCh. 5 - Prob. 5CTQCh. 5 - Prob. 6CTQCh. 5 - On which do you expect to have a more intense and...Ch. 5 - Prob. 8CTQCh. 5 - Prob. 9CTQCh. 5 - Prob. 10CTQ
Ch. 5 - Prob. 11CTQCh. 5 - Prob. 12CTQCh. 5 - Prob. 13CTQCh. 5 - Prob. 14CTQCh. 5 - Prob. 15CTQCh. 5 - Prob. 16CTQCh. 5 - For each proposed set of resonance structures: a....Ch. 5 - Consider the polarization of the C=O bond in the...Ch. 5 - The C=O double bond is called a “carbonyl bond.”...Ch. 5 - Prob. 20CTQCh. 5 - Prob. 21CTQCh. 5 - Prob. 22CTQCh. 5 - Prob. 23CTQCh. 5 - Prob. 24CTQCh. 5 - Prob. 25CTQCh. 5 - Prob. 26CTQCh. 5 - Prob. 27CTQCh. 5 - Prob. 28CTQCh. 5 - Prob. 29CTQCh. 5 - Prob. 30CTQCh. 5 - Prob. 31CTQCh. 5 - Confirm that there is no legitimate Lewis...Ch. 5 - Draw all resonance structures of the molecule...Ch. 5 - Prob. 34CTQCh. 5 - Prob. 35CTQCh. 5 - Prob. 36CTQCh. 5 - Occasionally, we will see an ionic compound that...Ch. 5 - Prob. 2ECh. 5 - Prob. 3ECh. 5 - Prob. 4ECh. 5 - Is it possible to draw a resonance structure of...Ch. 5 - Prob. 6ECh. 5 - Prob. 7ECh. 5 - Prob. 8ECh. 5 - Phenol (shown below) has a pKa10 . a. Based on pKa...Ch. 5 - Use curved arrows to show the most likely...Ch. 5 - Prob. 12ECh. 5 - Complete each Lewis structure, draw all important...Ch. 5 - Use curved arrows to show the most likely...Ch. 5 - Construct an explanation for why sulfuric acid is...Ch. 5 - Prob. 16ECh. 5 - Prob. 17ECh. 5 - Prob. 18E
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