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
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
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

What happens when we add some complexity to our s-cis-1,3-diene? We can form a bridged diels-alder product. It's a lot easier than it sounds, I promise! Let's take a look. 

Concept #1: Bridged-Products

Additional Problems
Which reaction would produce the following compound? A) I B) II C) III D) IV E) None of the above
Two constitutional isomers of molecular formula C13H22 are formed in the following reaction. Ignoring stereochemistry, suggest reasonable structures for the Diels-Alder adducts.
For the reaction or series of reaction below, draw the structure of the appropriate compound in the box provided. Indicate stereochemistry where it is pertinent.
What is the major product of the Diels-Alder reaction shown?
Predict the product for the reaction below. 
Predict the major product for each of the following reactions by paying attention to regio- and stereochemistry where appropriate.
Fill in the structure of the missing module of the reaction by paying attention to regio - and stereochemistry where necessary. 
The following compound undergoes an intramolecular Diels-Alder reaction to give a bicyclic product. Propose a structural formula for the product.
The Diels-Alder reaction involves the coupling between a diene and a dienophile. In the box below draw the structure of the bicyclic product obtained from the Diels-Alder reaction of the following compound with cyclopentadiene.
The above triene undergoes an intramolecular Diels-Alder reaction to give a polycyclic product. In the box below draw the structure of the expected product.
The following compound undergoes an intramolecular Diels-Alder reaction to give a bicyclic product. Propose a structural formula for the product. You do not have to consider stereochemistry. In cases where there is more than one answer, just draw one.
Which of the following diene(s) can not undergo the Diels-Alder reaction? (a) I(b) II(c) III(d) IV(e) I & IV