Textbook Question
For each of the following reactions, identify the bonds that are broken and formed. Be sure to indicate whether the bond that is broken is a σ bond or a π bond.
(e)
1250
views
Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics
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. 5 - Chemical Reaction Analysis: Thermodynamics and KineticsProblem 49a
Mullins 1st EditionCh. 5 - Chemical Reaction Analysis: Thermodynamics and KineticsProblem 49aChapter 4, Problem 49a
For each of the following reactions, identify the bonds that are broken and formed. Be sure to indicate whether the bond that is broken is a σ bond or a π bond.
(a) 
Verified step by step guidance1
Step 1: Analyze the reactants and products. The reactants are acetic acid (CH3COOH) and isopropyl bromide ((CH3)2CHBr). The products are isopropyl acetate (CH3COOCH(CH3)2) and HBr.
Step 2: Identify the bonds broken in the reaction. In acetic acid, the O-H σ bond is broken. In isopropyl bromide, the C-Br σ bond is broken.
Step 3: Identify the bonds formed in the reaction. A new C-O σ bond is formed between the carbonyl oxygen of acetic acid and the isopropyl group. Additionally, an H-Br σ bond is formed.
Step 4: Classify the bonds broken and formed. Both the bonds broken (O-H and C-Br) and the bonds formed (C-O and H-Br) are σ bonds. No π bonds are involved in this reaction.
Step 5: Summarize the reaction mechanism. This is an example of a nucleophilic acyl substitution reaction, where the nucleophile (isopropyl group) replaces the hydroxyl group of acetic acid, forming an ester and HBr as byproducts.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Was this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Types of Chemical Bonds
In organic chemistry, bonds between atoms can be classified as sigma (σ) or pi (π) bonds. Sigma bonds are formed by the head-on overlap of atomic orbitals and are the first bonds formed between two atoms. Pi bonds, on the other hand, result from the side-to-side overlap of p orbitals and are typically found in double and triple bonds. Understanding these bond types is crucial for analyzing reactions.
Recommended video:
3:11
Chemical Reactions of Phosphate Anhydrides Concept 1
Reaction Mechanisms
A reaction mechanism describes the step-by-step process by which reactants are converted into products. It includes the breaking and forming of bonds, which can involve the movement of electrons. Identifying the specific bonds broken and formed during a reaction helps in understanding the mechanism and predicting the outcome of the reaction.
Recommended video:
Guided course
02:16Heck Reaction Mechanism
Nucleophiles and Electrophiles
In organic reactions, nucleophiles are species that donate an electron pair to form a bond, while electrophiles are electron-deficient species that accept an electron pair. In the given reaction, the hydroxyl group (OH) acts as a nucleophile, attacking the electrophilic carbon in the alkyl bromide. Recognizing these roles is essential for determining which bonds are broken and formed during the reaction.
Recommended video:
Guided course
03:Nucleophile or Electrophile
Related Practice
Textbook Question
For each of the following acid–base reactions, (iv) draw the transition state, paying close attention to the degree of bond forming and breaking present in the transition state. If a pKa is not one of the ten common ones we learned in Chapter 4, it will be given to you.
(a)
812
views
Textbook Question
For each of the following acid–base reactions, (ii) calculate Keq. If a pKa is not one of the ten common ones we learned in Chapter 4, it will be given to you.
(a)
1294
views
Textbook Question
For each of the following acid–base reactions, (iii) calculate ∆G°. If a pKa is not one of the ten common ones we learned in Chapter 4, it will be given to you.
(a)
1154
views
Textbook Question
For each of the following reactions, identify the bonds that are broken and formed. Be sure to indicate whether the bond that is broken is a σ bond or a π bond.
(c)
1150
views
Textbook Question
The A value of a substituent on a cyclohexane ring is essentially the ∆G° for a substituent going from the equatorial to the axial position in a chair–chair interconversion. Because most substituents prefer to be in the equatorial position, A values are, by definition, positive numbers. Use the table of A values to calculate ∆G° and Keq for the chair–chair interconversions shown.
(a)
888
views