Textbook Question
Two resonance structures are shown for each molecule. Use the arrow-pushing formalism to represent the electron flow from the structure on the left to the one on the right.
(d)
1
views
Ch. 2 - General Chemistry Translated: Finding the Electrons
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
Not the one you use?Change textbookSelect a different textbook
Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
All textbooks
Mullins 1st EditionCh. 2 - General Chemistry Translated: Finding the ElectronsProblem 64b
Mullins 1st EditionCh. 2 - General Chemistry Translated: Finding the ElectronsProblem 64bChapter 1, Problem 64b
Two resonance structures are shown for each molecule. Use the arrow-pushing formalism to represent the electron flow from the structure on the left to the one on the right.
(b) 
Verified step by step guidance1
Identify the changes between the two resonance structures. Look for differences in the placement of π bonds, lone pairs, or formal charges.
Determine the starting point of the electron flow. Typically, this will involve lone pairs or π bonds that are moving to form new bonds or redistribute electron density.
Use curved arrows to represent the movement of electrons. Each arrow starts at the electron source (a lone pair or a bond) and points to where the electrons are moving (a bond or an atom).
Ensure that the octet rule is satisfied for all atoms in the resulting resonance structure, and adjust formal charges accordingly.
Double-check that the total number of electrons and the net charge remain the same between the two resonance structures, as resonance does not change the overall electron count or charge.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
2mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Resonance Structures
Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. They are used to represent molecules where a single Lewis structure cannot adequately depict the electron distribution. Each resonance structure contributes to the overall hybrid structure, which is a more accurate representation of the molecule's actual electron configuration.
Recommended video:
Guided course
03:04
Drawing Resonance Structures
Arrow-Pushing Formalism
Arrow-pushing formalism is a method used in organic chemistry to depict the movement of electrons during chemical reactions. Curved arrows indicate the direction of electron flow, showing how bonds are formed or broken. This technique helps visualize mechanisms and understand how reactants transform into products, making it essential for analyzing resonance and reaction pathways.
Recommended video:
Guided course
01:34Calculating formal and net charge.
Electron Delocalization
Electron delocalization refers to the distribution of electrons across multiple atoms in a molecule, rather than being localized between two specific atoms. This phenomenon is crucial in resonance structures, as it allows for the stabilization of molecules through the sharing of electrons. Delocalization often leads to lower energy states and increased stability, influencing the reactivity and properties of organic compounds.
Recommended video:
Guided course
03:54The 18 and 16 Electron Rule
Related Practice
Textbook Question
In the following molecules, identify all pushable electron pairs.
(a)
1
views
Textbook Question
Draw the Lewis structure for the following molecular formulas.
(v) CH5N
1
views
Textbook Question
Two resonance structures are shown for each molecule. Use the arrow-pushing formalism to represent the electron flow from the structure on the left to the one on the right.
(e)
1
views
Textbook Question
Draw the Lewis structure for the following molecular formulas.
(u) NH4+
1
views
Textbook Question
Two resonance structures are shown for each molecule. Use the arrow-pushing formalism to represent the electron flow from the structure on the left to the one on the right.
(f)
1
views