Ch. 16 - Conjugated SystemsWorksheetSee 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
Conjugation Chemistry
Stability of Conjugated Intermediates
Allylic Halogenation
Conjugated Hydrohalogenation (1,2 vs 1,4 addition)
Diels-Alder Reaction
Diels-Alder Forming Bridged Products
Diels-Alder Retrosynthesis
Molecular Orbital Theory
Drawing Atomic Orbitals
Drawing Molecular Orbitals
HOMO LUMO
Orbital Diagram: 3-atoms- Allylic Ions
Orbital Diagram: 4-atoms- 1,3-butadiene
Orbital Diagram: 5-atoms- Allylic Ions
Orbital Diagram: 6-atoms- 1,3,5-hexatriene
Orbital Diagram: Excited States
Pericyclic Reaction
Thermal Cycloaddition Reactions
Photochemical Cycloaddition Reactions
Thermal Electrocyclic Reactions
Photochemical Electrocyclic Reactions
Cumulative Electrocyclic Problems
Sigmatropic Rearrangement
Cope Rearrangement
Claisen Rearrangement
Additional Practice
Conjugated Halogenation
Diels-Alder Inductive Effects
Diels-Alder Regiospecficity
Diels-Alder Asymmetric Induction
Diels-Alder Synthesis
Allylic SN1 and SN2
Cumulative Orbital Diagram Problems
Cumulative Cycloaddition Reactions
Cumulative Sigmatropic Problems
UV-Vis Spect Basics
UV-Vis Spect Beer's Law
Molecular Electronic Transition Therory
Woodward-Fieser Rules
Additional Guides
Diene

Imagine you are given the final cyclization product for a diels-alder reaction and asked which diene and dienophile were required to make the 6-membered ring in the first place. What do you do?

It turns out the process is a lot easier than you might think.  

Concept #1: Diels-Alder Retrosynthesis

Here is a summary of those steps: 

So now that we know the process, let's go ahead and apply it to the following molecules:

Example #1: Retrosynthesis

Example #2: Retrosynthesis

Additional Problems
What diene and dienophile would react to give the following Diels-Alder product TM?
Add the missing starting materials, reagents, or products (aqueous workup where necessary). Please use the boxes provided. Don't forget to show stereochemistry!
Fill in the structure of the missing module of the reaction by paying attention to regio - and stereochemistry where necessary. 
Provide unambiguous structural formulas for the missing organic compounds. 
What compound below will undergo a Diels-Alder reaction with benzyne to yield the product shown below? a) Cyclohexane b) Cyclohexene c) 1,3-Cyclohexadiene d) 1,4-Cyclohexadiene e) None of the above
Suggest reagents suitable for carrying out each step in the following synthetic sequence:   
With which reagents can the ketone shown be prepared via a Diels-Alder reaction?
Draw the structure of the alkyne most likely to be the dienophile starting material in the synthesis of the following molecule.
Identify the diene needed for the following reaction a. 1,3-pentadiene b. 1,4-pentadiene c. 2-methyl-1,3 butadiene d. 1-methyl-1,3-cyclohexadiene  e. none of these
What is the major product of the following reaction?
Draw the structures of the diene and dienophile (including proper alkene geometries) that most likely give rise to the following Diels-Alder product. 
Fill in the structure of the missing module of the reaction by paying attention to regio - and stereochemistry where necessary. 
Show how the following compound could be prepared in a two-step synthesis in which the first step involves a Diels-Alder reaction between an appropriate diene and dienophile.
Fill the gaps in the following reaction scheme.
This compound was formed by a Diels-Alder reaction. In the box below draw the structures of the diene and the dienophile that were used to form this product.
This compound was formed by a Diels-Alder reaction. In the box below draw the structures of the diene and the dienophile that were used to form this product.
Draw structural formulas for the diene and dienophile that combine in a Diels-Alder reaction to form the product shown. Consider E/Z stereochemistry of alkenes.