Ch. 18 - Reactions of Aromatics: EAS and BeyondWorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins
Sections
Electrophilic Aromatic Substitution
Benzene Reactions
EAS: Halogenation Mechanism
EAS: Nitration Mechanism
EAS: Friedel-Crafts Alkylation Mechanism
EAS: Friedel-Crafts Acylation Mechanism
EAS: Any Carbocation Mechanism
Electron Withdrawing Groups
EAS: Ortho vs. Para Positions
Acylation of Aniline
Limitations of Friedel-Crafts Alkyation
Advantages of Friedel-Crafts Acylation
Blocking Groups - Sulfonic Acid
EAS: Synergistic and Competitive Groups
Side-Chain Halogenation
Side-Chain Oxidation
Birch Reduction
EAS: Sequence Groups
EAS: Retrosynthesis
Diazo Replacement Reactions
Diazo Sequence Groups
Diazo Retrosynthesis
Nucleophilic Aromatic Substitution
Benzyne
Additional Practice
EAS: Sulfonation Mechanism
EAS: Gatterman–Koch Reaction
EAS: Total Benzene Isomers
EAS: Polycyclic Aromatic Hydrocarbons
EAS: Directing Effects
Resonance Theory of EAS Directing Effects
EAS: Badass Activity Chart
Activated Benzene and Polysubstitutions
Clemmensen Reduction
EAS: Dueling Benzenes
Hydrogenation of Benzene
EAS: Missing Reagent
EAS: Synthesis
Diazonization of Aniline
Diazo Coupling Reactions
SNAr vs. Benzyne
Aromatic Missing Reagent
Aromatic Synthesis
Aromatic Retrosynthesis
EAS on 5-membered Heterocycles
LearnAdditional Practice
Next SectionEAS: Ortho vs. Para Positions

Solution: Methyl p-nitrobenzoate has been found to undergo saponification (hydrolysis) faster than methyl benzoate. a. Consider the mechanism of saponification, and explain the reason for this rate enhancement.      b. Would you expect methyl p-methoxybenzoate to undergo saponification faster or slowerthan methyl benzoate? WHY?

Solution: Methyl p-nitrobenzoate has been found to undergo saponification (hydrolysis) faster than methyl benzoate. a. Consider the mechanism of saponification, and explain the reason for this rate enhancement.

Problem

Methyl p-nitrobenzoate has been found to undergo saponification (hydrolysis) faster than methyl benzoate. 

a. Consider the mechanism of saponification, and explain the reason for this rate enhancement.

 

 

 

 

 

 

b. Would you expect methyl p-methoxybenzoate to undergo saponification faster or slower

than methyl benzoate? WHY?

Next
Practice Problems
In electrophilic aromatic substitution reactions a...
Which of the following compounds reacts most slowl...
In electrophilic aromatic substitution reactions t...
Which one of the following compounds will be least...
Which compound is more reactive than benzene in el...
It's dipole roundup! Indicate which of the molecul...
Circle the benzene rings with a deactivating group...
Circle the compound that would react the fastest i...
Which one of the following would most readily unde...
The major product of the following reaction is 
Rank 1, 2, 3 and 4 (1 = fastest to 4 = slowest) th...
Which reagent would you use to carry out the follo...
Predict the major product for each of the followin...
Which one of the following compounds would be most...
Methyl p-nitrobenzoate has been found to undergo s...
Which of the following is the major product of the...
Which of the following compounds is most deactivat...
Supply the mechanism and structure of the major pr...
Which compound has the slowest rate toward an elec...
Which substituents would deactivate benzene toward...
Complete the following reaction by drawing the str...
Which statement best describes why anisole bromina...
Complete the following reaction by drawing the str...
Provide the expected major product (One-Step EAS):
Provide the expected major product (One-Step EAS):
Provide the expected major product (One-Step EAS):Draw the major organic product(s) for the followin...Draw the major product(s) that result from the fol...Draw the structure of the expected major organic p...Give the structures of the two major products in t...Predict the major product for the following reacti...The following compounds are treated with HNO3/H2SO...For the following reaction, draw the major organic...Draw the major organic product(s) for the followin...Draw the major organic product(s) for the followin...What is (are) the product(s)?Draw structural formulas for the major organic pro...Draw the structure of the product in the following...Draw the major product(s) that result from the fol...Draw the major organic product(s) for the followin...
Previous SectionEAS: Any Carbocation Mechanism
Next SectionEAS: Ortho vs. Para Positions