Concept explainers
Interpretation:
Theproducts formed from Diels Alder reaction of (2Z,4Z)-hexa-2,4-diene with methyl propenoate are to be determined.
Concept introduction:
A Diels Alder reaction is one between a conjugate diene and a reactant containing a double bond (dienophile) to form a product. The product is called adduct.
Diels Alder reactions are highly stereospecific. The configuration of the dienophile is retained in the product and the reaction is a syn addition reaction.
The dienes react with dienophiles in cis forms rather than trans forms.
Endo and exo refer to the orientation of the dienophile and its electron-withdrawing group when it reacts with a diene in a Diels Ander reaction.
Endo is favored in the transition state of aDiels Ander reaction because it has a lower energy.
Want to see the full answer?
Check out a sample textbook solutionChapter 13 Solutions
Organic Chemistry
- Draw the reactants that would react to form this cyclohexene derivative in a Diels-Alder reaction. Include any relevant stereochemical configurations. Draw Diene ✔ Iarrow_forwardStep 6: Now that you have determined the substrates and mechanism of a Diels-Alder reaction, you will learn how to recognize when you should use the Diels-Alder reaction. In a synthesis reaction, if you are given a cyclohexene product with no other obvious functional group transformations and an electron-withdrawing group two carbons away from the alkene, it is likely made via the Diels-Alder reaction. Deduce the structures of the starting materials to form the Diels-Alder adduct shown. ..... CN CN Diene + Dienophilearrow_forwardFor the following dienes, identify whether the molecules has any cis or trans stereochemistry and idenfity the conformation as either s-cis or s-trans, where appropriate. Please also note whether the compound would be reactive in a Diels -Alder reactionarrow_forward
- From trans-1-chloro-2-isopropylcyclohexane, only 3-isopropylcyclohexene, the less substituted alkene, is formed. Using conformational analysis, explain why this product is observed. Also, will the E2 reaction with trans-1-chloro- 2-isopropylcyclohexane or cis-1-chloro-2-isopropylcyclohexane occur faster under the same basic conditions? CH;O Na* CH3OH CI trans-1-Chloro-2 (R)-3-Isopropylcyclohexene isopropylcyclohexanearrow_forward2) The Diels-Alder reaction, developed by German chemists Otto Diels and Kurt Alder (who received the Nobel Prize in 1950 for their discovery), has great synthetic importance due to the possibility of forming an unsaturated six-membered cycle without involving intermediates ionic. About the reaction, answer: (a) Indicate the reagents necessary for the synthesis of the following compounds, indicating who is the diene and who is the dienophile.arrow_forwardUsing the Woodward–Hoffmann rules, predict the stereochemistry of belowreaction. a thermal [5,5] sigmatropic rearrangementarrow_forward
- Draw the reactants that would react to form this cyclohexene derivative in a Diels-Alder reaction. Include any relevant stereochemical configurations. { Edit Diene + Draw Dienophile Qarrow_forwardDraw the reactants that would react to form this cyclohexene derivative in a Diels-Alder reaction. Include any relevant stereochemical configurations. Qarrow_forwardCompounds X and Y are both C5H11CI products formed in the radical chlorination of pentane. Base-promoted E2 elimination of X and Y gives, in each case, a single C5H10 alkene (ignoring double bond stereochemistry). Both X and Y react in SN2 fashion with sodium iodide in acetone; Y reacts faster than X. What is the structure of Y? • Do not use stereobonds in your answer. • In cases where there is more than one possible structure for each molecule, just give one for each. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. ChemDoodle (Previous Nextarrow_forward
- How do you account for the marked difference in stability of these two ketones?arrow_forwardThis is a Diels-Alder reaction between ethylene and cis-1,3-butadiene. For each cycloaddition product, draw in all hydrogen atoms, and write the molecular formula below.arrow_forward14.26 Predict the products of the following Diels-Alder reactions: (a) (b)arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning