Textbook Question
Determine whether the following pairs of structures are actually different compounds or simply resonance forms of the same compounds.
a.
b.
c.
d.
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Ch.1 - Structure and Bonding
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 1, Problem 40d,e,f
For each of the following structures,
1. Draw a Lewis structure; fill in any nonbonding electrons.
2. Calculate the formal charge on each atom other than hydrogen
d. [(CH3)3O]+
e. CH3NC
f. (CH3)4NBr
Verified step by step guidance1
Step 1: For each molecule, start by identifying the total number of valence electrons. For example, in [(CH3)3O]+, calculate the valence electrons for carbon, hydrogen, and oxygen, and adjust for the positive charge.
Step 2: Draw the skeletal structure of the molecule. For [(CH3)3O]+, place the oxygen atom in the center with three CH3 groups attached to it. For CH3NC, connect the carbon atoms in a chain with nitrogen at the end. For (CH3)4NBr, place nitrogen in the center with four CH3 groups and a bromine ion nearby.
Step 3: Distribute the valence electrons around the atoms to satisfy the octet rule, starting with the outer atoms. Remember to account for the positive charge in [(CH3)3O]+ by removing one electron from the total count.
Step 4: Calculate the formal charge for each atom using the formula: Formal Charge = (Valence electrons) - (Nonbonding electrons) - 0.5*(Bonding electrons). Apply this to each atom in the structures, excluding hydrogen.
Step 5: Adjust the structure if necessary to minimize formal charges, ensuring that the most electronegative atoms carry negative charges if possible. Verify that the total charge of the molecule matches the given charge.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Lewis Structures
Lewis structures are diagrams that represent the bonding between atoms of a molecule and the lone pairs of electrons that may exist. They are essential for visualizing the arrangement of atoms, the distribution of electrons, and the connectivity within a molecule. To draw a Lewis structure, count the total valence electrons, arrange the atoms, and distribute the electrons to satisfy the octet rule for each atom.
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04:12
Drawing the Lewis Structure for N2H4.
Formal Charge Calculation
Formal charge is a theoretical charge assigned to an atom in a molecule, calculated using the formula: Formal Charge = (Valence Electrons) - (Nonbonding Electrons) - (Bonding Electrons/2). It helps in determining the most stable Lewis structure by ensuring that the sum of formal charges in a molecule equals the overall charge of the molecule. Atoms in a molecule are ideally assigned formal charges as close to zero as possible.
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01:34Calculating formal and net charge.
Nonbonding Electrons
Nonbonding electrons, also known as lone pairs, are valence electrons that are not shared with another atom in a covalent bond. They are important in determining the shape and reactivity of molecules, as they occupy space and can influence molecular geometry according to VSEPR theory. In Lewis structures, nonbonding electrons are represented as pairs of dots around the atom.
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Related Practice
Textbook Question
1. From what you remember of electronegativities, show the direction of the dipole moments of the following bonds.
2. In each case, predict whether the dipole moment is relatively large (electronegativity difference >0.5) or small.
a. C—Cl
b. C—H
c. C—Li
d. C—N
e. C—O
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Textbook Question
Determine whether the following pairs of structures are actually different compounds or simply resonance forms of the same compounds.
e.
f.
g.
h.
1564
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1
rank
Textbook Question
Give the molecular formula of each compound shown
(g)
(h)
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Textbook Question
Give the molecular formula of each compound shown
(d)
(e)
(f)
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Textbook Question
Determine whether the following pairs of structures are actually different compounds or simply resonance forms of the same compounds.
i.
j.
k.
l.
970
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