Name: Diels&#8211;Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Uploaded: 2023-04-30T11:33:02
Description: Learn by watching this video about Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry at JoVE.com

While Diels&#8211;Alder reactions between an acyclic diene and a dienophile give cyclic products, cyclic dienes form bridged bicyclic compounds.
Unlike the open-chain dienes, cyclic analogs are locked in an s-cis conformation, leading to rapid Diels&#8211;Alder reactions.
Reactions between cyclic dienes and substituted dienophiles give stereoselective results based on the relative alignment of the two components.
When the dienophile aligns with its electron-withdrawing group under the diene, the approach leads to an endo product.
Alternatively, when the electron-withdrawing group is directed away from the diene, the approach results in an exo product.
The two stereoisomers differ in the orientation of the substituent relative to the double bond.
In general, the major product is endo because the activation energy to its transition state is lowered, given the additional interaction between the electron-withdrawing group of the dienophile and the diene. This interaction, called secondary orbital overlap, is absent in the exo transition state.
Consequently, the endo product is formed faster and is the kinetic product. Whereas, the exo product is sterically favored and is the thermodynamic product.

diels&ndash;alder reaction forming bridged bicyclic products: stereochemistry

Diels&#8211;Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
<img alt="Figure1" src="/files/ftp_upload/13095/13095_PT_Figure_1.svg" style="text-align: center; height: 75px;" />
Dienophiles with one or more electron-withdrawing substituents form stereochemically different products in which the substituents are oriented in an endo (towards) or exo (away) configuration relative to the double bond.
<img alt="Figure2" src="/files/ftp_upload/13095/13095_PT_Figure_2.svg" style="text-align: center; height: 105px;" />
The endo isomer is formed faster and is the kinetic product. The exo isomer is more stable and is the thermodynamic product.

Learn by watching this video about Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry at JoVE.com

Diels&#8211;Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels&ndash;Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels&#8211;Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

Dienophiles with one ...

dielsalder-reaction-forming-bridged-bicyclic-products-stereochemistry

Education

JoVE Core

Organic Chemistry

Unit 1

Dienes, Conjugated Pi Systems, and Pericyclic Reactions

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unit 1

covalent bonding and structure

Covalent Bonding and Structure

Chapter 1 thermodynamics and chemical kinetics

Thermodynamics and Chemical Kinetics

Chapter 2 alkanes and cycloalkanes

Alkanes and Cycloalkanes

Chapter 3 stereoisomerism

Stereoisomerism

Chapter 4 acids and bases

Acids and Bases

Chapter 5 nucleophilic substitution and elimination reactions of alkyl halides

Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

Chapter 6 alkene structure and reactivity

Alkene Structure and Reactivity

Chapter 7 reactions of alkenes

Reactions of Alkenes

Chapter 8 alkynes

Alkynes

Chapter 9 alcohols and phenols

Alcohols and Phenols

Chapter 10 ethers, epoxides, sulfides

Ethers, Epoxides, Sulfides

Chapter 11 aldehydes and ketones

Aldehydes and Ketones

Chapter 12 carboxylic acids

Carboxylic Acids

Chapter 13 carboxylic acid derivatives

Carboxylic Acid Derivatives

Chapter 14 &alpha;-carbon chemistry: enols, enolates, and enamines

&alpha;-Carbon Chemistry: Enols, Enolates, and Enamines

Chapter 15 dienes, conjugated pi systems, and pericyclic reactions

Chapter 16 aromatic compounds

Aromatic Compounds

Chapter 17 reactions of aromatic compounds

Reactions of Aromatic Compounds

Chapter 18 amines

Amines

Chapter 19 radical chemistry

Radical Chemistry

Chapter 20 synthetic polymers

Synthetic Polymers

Chapter 21 key terms and concepts

scientists in action

SCIENTISTS IN ACTION

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The addition of a hydrogen halide to 1,3-butadiene gives a mixture of 1,2- and 1,4-adducts. Since more substituted alkenes are more stable, the 1,4-adduct ...

uv&ndash;vis spectroscopy of conjugated systems

UV&ndash;Vis Spectroscopy of Conjugated Systems

Organic compounds with conjugated double bonds show strong absorption features in the UV&ndash;visible region of the electromagnetic spectrum attributed ...

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UV&ndash;Vis Spectroscopy: Woodward&ndash;Fieser Rules

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pericyclic reactions: introduction

Pericyclic Reactions: Introduction

Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the ...

thermal and photochemical electrocyclic reactions: overview

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Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two ...

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Structure of Conjugated Dienes

Stability of Conjugated Dienes

π Molecular Orbitals of 1,3-Butadiene

π Molecular Orbitals of the Allyl Cation and Anion

π Molecular Orbitals of the Allyl Radical

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

Electrophilic 1,2- and 1,4-Addition of X₂ to 1,3-Butadiene

Electrophilic Addition of HX to 1,3-Butadiene: Thermodynamic vs Kinetic Control

UV–Vis Spectroscopy of Conjugated Systems

UV–Vis Spectroscopy: Woodward–Fieser Rules

Pericyclic Reactions: Introduction

Thermal and Photochemical Electrocyclic Reactions: Overview

Thermal Electrocyclic Reactions: Stereochemistry

Photochemical Electrocyclic Reactions: Stereochemistry