Textbook Question
Explain why the pKa of p-nitrophenol is 7.14, whereas the pKa of m-nitrophenol is 8.39.
1769
views
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 Benzene
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. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of BenzeneProblem 27c
Bruice 8th EditionCh. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of BenzeneProblem 27cChapter 9, Problem 27c
What is the major product of each of the following reactions, assuming that one equivalent of each reagent is used in each reaction?
c. 
Verified step by step guidance1
Step 1: Identify the type of reaction. The given reaction involves an alkene reacting with HBr (hydrobromic acid). This is an electrophilic addition reaction where the alkene undergoes protonation followed by nucleophilic attack.
Step 2: Determine the regioselectivity of the reaction. According to Markovnikov's rule, the hydrogen atom from HBr will add to the carbon of the double bond that has more hydrogens, while the bromine atom will add to the carbon with fewer hydrogens.
Step 3: Analyze the structure of the alkene. The double bond is located in a cyclopentene ring. The carbon atoms in the double bond are sp2 hybridized, and one of them will receive the hydrogen while the other will receive the bromine.
Step 4: Consider the carbocation intermediate. When the hydrogen adds to the less substituted carbon, a more stable carbocation intermediate is formed on the more substituted carbon. This stability is due to hyperconjugation and inductive effects.
Step 5: Complete the reaction by adding the bromine. The bromide ion (Br⁻) will attack the carbocation, leading to the formation of the major product. The bromine will be attached to the more substituted carbon of the original double bond.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
4mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Hydrohalogenation
Hydrohalogenation is an electrophilic addition reaction where a hydrogen halide (like HBr) adds across a double bond in an alkene. The reaction typically follows Markovnikov's rule, which states that the hydrogen atom from the hydrogen halide will attach to the carbon with the greater number of hydrogen atoms, leading to the formation of the more stable carbocation intermediate.
Recommended video:
Guided course
04:07
General properties of hydrohalogenation.
Markovnikov's Rule
Markovnikov's rule is a principle used to predict the outcome of electrophilic addition reactions. It states that when HX (where X is a halogen) adds to an unsymmetrical alkene, the hydrogen atom will bond to the carbon atom that has the most hydrogen atoms already attached, while the halogen will bond to the carbon with fewer hydrogen atoms. This results in the formation of the more stable product.
Recommended video:
Guided course
03:54The 18 and 16 Electron Rule
Carbocation Stability
Carbocation stability is a key concept in organic chemistry that refers to the relative stability of positively charged carbon species. Carbocations are stabilized by electron-donating groups and are more stable when they are tertiary (attached to three other carbons) compared to secondary or primary carbocations. The stability of the carbocation formed during hydrohalogenation influences the major product of the reaction.
Recommended video:
Guided course
05:58Determining Carbocation Stability
Related Practice
Textbook Question
What are the products of the following reactions, assuming that one equivalent of each reagent is used in each reaction?
b.
1208
views
Textbook Question
Which of the double bonds in zingiberene, the compound responsible for the aroma of ginger, is most reactive in an electrophilic addition reaction with HBr?
1423
views
Textbook Question
What is the major product obtained from the addition of HBr to the following compound?
1101
views
Textbook Question
What is the major product of each of the following reactions, assuming that one equivalent of each reagent is used in each reaction?
b.
1285
views
Textbook Question
What are the products of the following reactions, assuming that one equivalent of each reagent is used in each reaction?
c.
1286
views