For the Diels-Alder reaction, the product's skeletal structure and configuration at the bridgehead carbons are given (and the given wedge bond and dash bond should not be changed). Complete the structure of the major product. Indicate the stereochemistry, by adding two wedge and two dash bonds, at only the fused-ring stereocenters. A Complete the product and clearly show stereochemistry. Select Draw Rings More H G = H C H 0 ° Erase Q2 Q

For the Diels-Alder reaction, the product's skeletal structure and configuration at the bridgehead carbons are given (and the given wedge bond and dash bond should not be changed). Complete the structure of the major product. Indicate the stereochemistry, by adding two wedge and two dash bonds, at only the fused-ring stereocenters. A Complete the product and clearly show stereochemistry. Select Draw Rings More H G = H C H 0 ° Erase Q2 Q

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy

Section14.SE: Something Extra

Problem 41AP: Although the Dielsâ€“Alder reaction generally occurs between an electronrich diene and an...

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A very large number of Diels-Alder reactions are recorded in the chemical literature, many of which involve relatively complicated dienes, dienophiles, or both. Predict the constitution of the Diels-Alder adduct that is expected to form from the combination of diene and dienophile below. Draw the structure of the predicted product, including relevant stereochemistry when applicable. If applicable, use the Bicyclic Stamp tool and guide points to draw each structure. Click and drag to start drawing a structure.
For the Diels-Alder reaction, the product's skeletal structure and configuration at the bridgehead carbons are given (and the given wedge bond and dash bond should not be changed). Complete the structure of the major product. Indicate the stereochemistry, by adding two wedge and two dash bonds, at only the fused-ring stereocenters. Complete the product and clearly show stereochemistry. Select Draw Rings More Erase C H H H
Although the Dielsâ€“Alder reaction generally occurs between an electronrich diene and an electron-deficient dienophile, it is also possible to have inverse-demand Dielsâ€“Alder reactions between suitable electrondeficient conjugated double bonds and electron-rich alkenes. These reactions are particularly useful because they allow for the incorporation of heteroatoms into the new six-membered ring. Predict the products of each inverse-demand Dielsâ€“Alder reaction below. Be sure your products reflect the correct stereochemistry. If more than one regioisomer is possible, draw both.
Draw and discuss the mechanism (with arrows to show electron movements) of the Diels-Alder reaction between anthracene and maleic anhydride. Draw the orientation and phases of the reacting p-orbitals showing how they overlap in a “suprafacial” geometry to form product
Which of the following statments is TRUE about the Diels-Alder cycloaddition reaction? The best reactions occur with an electron-rich diene and an electron-poor dienophile. The reaction favors the exo-product. Entropy drives the reaction toward the cyclohexene product. The reaction is not stereospecific with respect to the dienophile stereochemistry.
The highly reactive triple bond of benzyne is a powerful dienophile. Predict the productof the Diels–Alder reaction of benzyne (from chlorobenzene and NaOH, heated) withcyclopentadiene.
(a) Complete the following sequence of reactions (i.e., give the structure for compounds A and B), giving structural details of all key intermediates. heat & A COOCH3 H₁₂ Ni (b) Provide the bond line structures for the pair of compounds used for the Diels-Alder synthesis of the compound shown below. O B COOCH3 (c) Draw the two major products obtained when (3E,5Z)-2,2,3,6,7-pentamethylocta-3,5-diene reacts with HBr at low and high temperatures. Label the products as the kinetic or thermodynamic product AND, if applicable, use dashes and wedges to show the correct stereochemistry in the obtained products.
(a) For the reaction of 1-methoxy-4-methylbenzene with CH3C(O)CI in the presence of AICI3, describe the bonding and electron distribution in 1-methoxy- 4-methylbenzene, formation and structure of the electrophile in the reaction, and the most stable intermediate responsible for the end product. i H3C1 CI, AICI 3 Me- -OMe 1-methoxy-4-methylbenzene (b) Use phenol as the substrate, propose a synthetic scheme to produce 2-allyl-4-bromophenol (Mechanism not required). Br OH OH phenol 2-allyl-4-bromophenol (c) Propose a synthesis of Compound A starting from benzaldehyde and other necessary reagents of your choice (Mechanism not required). OH CHO CI. Compound A benzaldehyde (d) For the given 13C NMR chemical shifts of the carbonyl carbons in the order of ketones > aldehydes > carboxylic acids, provide an explanation. O CH3 H3C. 13C NMR Chemical Shifts: H₂C1 H₂C H > OH 200 ppm 181 ppm 209 ppm
Give the structure of the main product of each of the following Diels-Alder reactions. Make sureto show the stereochemistry of the products when unambiguous.
Which of the following compounds can arise directly from a Diels-Alder reaction? Please circle any structures that can, and then identify the appropriate diene(s) and dienophile(s) that would lead to that compound. Be sure to pay attention to E-IZ- stereochemistry in all of the reactants. For those that cannot undergo a Diels-Alder reaction, please explain why. OEt o CN .cO,Me Meo OMe H (+-) (+/-) (+/-) (+/-)
Step 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 + Dienophile
Write a general rule that can be used to predict the major product of a Diels–Alder reaction between an alkene with an electron-withdrawing substituent and a diene with a substituent that can donate electrons by resonance depending on the location of the substituent on the diene.