Textbook Question
We predicted that the products would have a 1,2- or 1,4-relationship of the proper substituents. Draw the charge-separated resonance forms of the reactants to support these predictions.
(a) (b)
1193
views
Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy
Wade9th EditionOrganic ChemistryISBN: 9780135213728
Not the one you use?Change textbookSelect a different textbook
Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
All textbooks
Wade 9th EditionCh. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet SpectroscopyProblem 15a,b,c
Wade 9th EditionCh. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet SpectroscopyProblem 15a,b,cChapter 15, Problem 15a,b,c
What dienes and dienophiles would react to give the following Diels–Alder products?
(a) 
(b) 
(c) 
Verified step by step guidance1
Step 1: Analyze the Diels–Alder product structure to identify the diene and dienophile components. The Diels–Alder reaction involves a conjugated diene reacting with a dienophile (an electron-deficient alkene or alkyne). Look for the cyclohexene ring in the product, which is characteristic of this reaction.
Step 2: For product (a), observe the cyclohexene ring with a ketone group (COCH₃) attached. The diene must have two conjugated double bonds, and the dienophile must contain a carbonyl group (C=O) to form this product. The diene is likely 1,3-cyclopentadiene, and the dienophile is methyl vinyl ketone (CH₂=CHCOCH₃).
Step 3: For product (b), observe the aromatic ring with a ketone group (COOCH₂CH₃) attached. The diene must have two conjugated double bonds, and the dienophile must contain an ester group (COOCH₂CH₃). The diene is likely 1,3-butadiene, and the dienophile is ethyl acrylate (CH₂=CHCOOCH₂CH₃).
Step 4: For product (c), observe the cyclohexene ring with a nitrile group (CN) attached. The diene must have two conjugated double bonds, and the dienophile must contain a nitrile group (C≡N). The diene is likely furan (a heterocyclic diene), and the dienophile is acrylonitrile (CH₂=CHCN).
Step 5: Verify the stereochemistry and regiochemistry of the products. The Diels–Alder reaction is stereospecific, meaning the stereochemistry of the diene and dienophile will influence the final product. Ensure that the substituents on the diene and dienophile align correctly to form the observed products.
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.
Diels–Alder Reaction
The Diels–Alder reaction is a [4+2] cycloaddition reaction between a conjugated diene and a dienophile, resulting in the formation of a six-membered ring. This reaction is a key method in organic synthesis for constructing cyclic compounds and is characterized by its stereospecificity and regioselectivity, making it a powerful tool for chemists.
Recommended video:
Guided course
04:02
Diels-Alder Retrosynthesis
Dienes
Dienes are organic compounds that contain two double bonds. They can be classified as conjugated, where the double bonds are separated by a single bond, or isolated, where the double bonds are separated by more than one single bond. Conjugated dienes are particularly important in Diels–Alder reactions due to their ability to stabilize the transition state and facilitate the cycloaddition process.
Recommended video:
Guided course
04:43Drawing MO Diagram for Dienes
Dienophiles
Dienophiles are compounds that contain a double or triple bond and can react with dienes in the Diels–Alder reaction. They are typically electron-deficient, which enhances their reactivity towards the electron-rich diene. Common examples include alkenes and alkynes, often substituted with electron-withdrawing groups to increase their reactivity in the cycloaddition process.
Recommended video:
Guided course
09:48General Features
Related Practice
Textbook Question
What dienes and dienophiles would react to give the following Diels–Alder products?
(d)
(e)
(f)
1015
views
Textbook Question
Predict the major product for each proposed Diels–Alder reaction. Include stereochemistry where appropriate.
(a)
1871
views
Textbook Question
Predict the products of the following proposed Diels–Alder reactions.
(d)
1308
views
Textbook Question
Predict the products of the following proposed Diels–Alder reactions.
(e)
1446
views
Textbook Question
Predict the products of the following proposed Diels–Alder reactions.
(f)
1023
views