Textbook Question
What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?
f. MCPBA (a peroxyacid)
1627
views
Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
Not the one you use?Change textbookSelect a different textbook
Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
All textbooks
Bruice 8th EditionCh. 6 - The Reactions of Alkenes • The Stereochemistry of Addition ReactionsProblem 58b
Bruice 8th EditionCh. 6 - The Reactions of Alkenes • The Stereochemistry of Addition ReactionsProblem 58bChapter 7, Problem 58b
What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?
b. HI
Verified step by step guidance1
Identify the type of reaction: The reaction of 2-methyl-2-butene with HI is an electrophilic addition reaction. The double bond in the alkene acts as a nucleophile, reacting with the electrophilic hydrogen (H⁺) from HI.
Determine the regioselectivity: This reaction follows Markovnikov's rule, which states that the hydrogen atom (H⁺) will add to the carbon of the double bond that has more hydrogen atoms already attached, while the iodine (I⁻) will add to the carbon with fewer hydrogen atoms.
Protonation of the double bond: The π-electrons of the double bond attack the H⁺ from HI, forming a carbocation intermediate. The more stable carbocation will form, which in this case is the tertiary carbocation at the carbon bonded to the methyl groups.
Nucleophilic attack: The iodide ion (I⁻) acts as a nucleophile and attacks the positively charged carbocation, forming the final product.
Draw the major product: The major product will be 2-iodo-2-methylbutane, where the iodine atom is attached to the carbon that was part of the double bond and now forms a single bond with iodine.
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.
Electrophilic Addition Reactions
Electrophilic addition reactions are a fundamental type of reaction in organic chemistry where an electrophile reacts with a nucleophile, typically involving alkenes. In this case, 2-methyl-2-butene, an alkene, will react with HI, where the hydrogen (H) acts as the electrophile and adds to one of the carbon atoms of the double bond, while the iodide (I) adds to the other.
Recommended video:
Guided course
05:39
Features of Addition Mechanisms.
Markovnikov's Rule
Markovnikov's Rule states that in the addition of HX to an alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached. This rule helps predict the major product of the reaction, as it guides the regioselectivity of the electrophilic addition, leading to the more stable carbocation intermediate.
Recommended video:
Guided course
03:54The 18 and 16 Electron Rule
Carbocation Stability
Carbocation stability is crucial in determining the outcome of reactions involving alkenes. Tertiary carbocations are more stable than secondary or primary ones due to hyperconjugation and inductive effects. In the reaction of 2-methyl-2-butene with HI, the formation of a more stable tertiary carbocation will favor the major product, which is influenced by the structure of the starting alkene.
Recommended video:
Guided course
05:58Determining Carbocation Stability
Related Practice
Textbook Question
What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?
a. HBr
2422
views
Textbook Question
Identify the electrophile and the nucleophile in each of the following reaction steps and then draw curved arrows to illustrate the bond-making and bondbreaking processes.
c.
700
views
Textbook Question
What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?
d. O3, −78 °C, followed by (CH3)2S
769
views
Textbook Question
What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?
g. H2O + H2SO4
1329
views
Textbook Question
Identify the electrophile and the nucleophile in each of the following reaction steps and then draw curved arrows to illustrate the bond-making and bondbreaking processes.
b.
663
views