Ch. 18 - Reactions of Aromatics: EAS and BeyondSee 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

EAS: Retrosynthesis

See all sections
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
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

So it turns out, you may be asked to propose an aromatic synthesis starting only from benzene or other benzene derivatives. We will use our previous knowledge of sequence groups to plan synthetic steps in the correct order

Concept #1: Aromatic synthesis starting with benzene/benzene derivatives

Example #1: Synthesize the target molecule

Example #2: Synthesize the target molecule

Practice: Provide the product for each of the following reaction steps

Practice: Beginning from Benzene, synthesize the following compound.

Practice: Beginning from Benzene, synthesize the following compound. 

1-Phenylethanol

Practice: Beginning from Benzene, synthesize the following compound.

Additional Problems
Propose the sythetic plan complete with reagents and proper order of reactions. You must show the product of each step in your scheme, however no detailed mechanism is required. 
Which sequence of reactions would give (some of) the correct product?  1) A and B 2) A and C 3) B and C 4) B only 5) A, B, and C 
Which sequence of reagents will accomplish this transformation?
Which sequence of reagents will effect this transformation?
Provide stepwise synthesis for the following transformation:
Which is the best method for carrying out the following reaction?
Provide the reagents to accomplish the transformation below. More than one step might be required for the transformation. 
Perform a retrosynthetic analysis on the molecules below (work backwards) from the given commercially available starting materials.
Starting with benzene, and using any other necessary reagants, design a synthesis for the following compound. Note: A reaction mechanism (i.e.; arrow-pushing) is not required.
Which set of reagents will best accomplish this transformation?    
Using any necessary reagents, show how you would accomplish the following transformations.  
Predict the major product for each of the following reactions paying attention to the region- and stereochemistry. If there is no reaction, write just “No Reaction.”  
For the reaction below, draw the structure of the appropriate compound in the box. Indicate stereochemistry where it is pertinent. For Friedel Crafts reactions, assume that the major product is the least sterically hindered one.
Propose a multi-step synthetic scheme complete with reagents and proper order of reactions (no mechanisms required) for the following molecule starting from the indicated compounds. You may use any reagents neccessary. Show the product of each step in your scheme.
Provide a scheme for the synthesis of the molecule below, using the indicated starting material and reagents of your choice.
Which sets of reagents would best be used to perform the following reaction?
Using any necessary reagents, show how you would accomplish the following transformations.
Circle the stating material for the following synthetic sequence.  
The following synthetic pathway does NOT sufficiently produce the indicated product. Provide an acceptable synthetic pathway. 
Propose a synthesis of compound B starting from benzene and acetyl chloride (CH3COCl ) as the only sources of carbon. Several steps may be required. Assume that all reagents needed for the synthesis are available. Indicate clearly the reagents used and the products obtained after each step. Mechanisms are not required.  
Propose a synthetic pathway from the indicated starting material to the designated product
Propose a synthetic pathway from the indicated starting material to the designated product
Provide the starting materials and reagents necessary to yield the product below.
Provide the reagents that will accomplish the following transformation. More than one step may be required.
Synthesize the trisubstituted benzene A from benzene.
Propose a synthesis of toulene starting from benzene and any other necessary reagents.
Propose a synthesis of acetophenone starting from benzene and any other necessary reagents.
Suggest a synthetic pathway from the given starting materials to the designated products.
Suggest a synthetic pathway from the given starting materials to the designated products.
Suggest a synthetic pathway from the given starting materials to the designated products.
Suggest a synthetic pathway from the given starting materials to the designated products.
Suggest a synthetic pathway from the given starting materials to the designated products.
Suggest a synthetic pathway from the given starting materials to the designated products.
Give the reagents needed to synthesize the desired products in high yields from the given starting materials
Provide reagent to complete the following chemical transformation.
Provide reagent to complete the following chemical transformation.
Provide reagent to perform the following transformation.
Suggest a synthetic pathway from the given starting material to the designated product.
Suggest a synthetic pathway from the given starting material to the designated product.
Suggest a synthetic pathway from the given starting material to the designated product.
Suggest a synthetic pathway from the given starting material to the designated product.
Suggest a synthetic pathway from the given starting material to the designated product.
Consider the following synthetic sequence and fill in the missing structures and/or reagents (ignore stereochemistry).
Starting with Benzene and using other reagents devise a synthesis for Methoxyphenyl acetamide.
In each reaction box, place the best reagent and conditions from the list below.
In each reaction box, place the best reagent and conditions from the list below.
In each reaction box, place the best reagent and conditions from the list below.
In each reaction box, place the best reagent and conditions from the list below. 
In each reaction box, place the best reagent and conditions from the list below. 
In each reaction box, place the best reagent and conditions from the list below.