7. Although the Diels-Alder reaction generally occurs between an electron-rich diene and an electron- deficient dienophile, it is also possible to have inverse-demand Diels-Alder reactions between suitable electron-deficient 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 Diels-Alder reaction below. Be sure your products reflect the correct stereochemistry. If more than one regio-isomer is possible, draw both.

7. Although the Diels-Alder reaction generally occurs between an electron-rich diene and an electron- deficient dienophile, it is also possible to have inverse-demand Diels-Alder reactions between suitable electron-deficient 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 Diels-Alder reaction below. Be sure your products reflect the correct stereochemistry. If more than one regio-isomer is possible, draw both.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

See similar textbooks

Similar questions

Need help with this question. Thank you :)
-A on 2. Which class of pericyclic reactions is the Diels-Alder reaction? What is a (4+ 2) n cycloaddition reaction? Explain •a cycloaddikon where ore reactant moleculee cortriautes 41 ele ctrons & the other a electrans 3. 4. (a) Give the systematic name of the diene in this reaction 15-cis)1,4-diphenyl-1,3-betadiene (b) Calculate the difference in the standard Yree energy, AG° (kJ/mol) between the two major conformations of this diene? (Write the formula and show your work.) = (-617.920458au- AGO Product- reactants k017.9259320 = 0.00S 47444K/ml.005474qu 14.37 KJ/ mol 1au= alas.KLcis) (trans) 5. Give the systematic name of the dienophile in this reaction. Maleie nhydride 6. Give the systematic name of the adduct in this reaction. 7. What is the melting point of your synthesized Diels-Alder adduct 8. Calculate the standard free energy of activation AG # for this reaction (Write the formula and show your work). AG = G75- G°R = (-994.1304ay au)-(-997.194182 au) - 0.039898au= .639898ay•…
4.- Predict the product for each Diels-Alder reaction. Indicate stereochemistry where appropriate. स a) b) H3C, H3C + H3C CHO A ent 10 150 COOH + ·E· <- c) COOH BAS 5.- Retro Diels-Alder: show a combination of diene and dienophile that would result in each Diels-Alder adduct.
12. Show the mechanism and the product of the following Diels-Alder reaction. (2) heat Х atic
Bromine in methylene chloride is added in stoichiometric proportions to cyclopentane, What color is the final solution? Bromine in methylene chloride is added in stoichiometric proportion to cyclohexa-1,3-diene. What color is the final solution?
When non-symmetrical dienes react with non-symmetrical dienophiles, there are two possible regioisomers to be formed as products. With this theoretical concept, predict the two possible products for the following Diels-Alder reaction. State which product is the major one and which is the minor one. OCH, OCH, ? + ? +
Predict the product of the following Diels-Alder reaction. Make sure to indicate stereochemistry whereverapplicable.
What is the product (include the stereochemistry) of the 6 pi electron electrocyclic reaction below, use the appropriate Woodward-Hoffman rule.
8) Draw the product of the Sn2 reaction illustrated below. Comment on the stereochemistry of the product: NaSH Sn2 Br ÓCH3 .
T. R. Hoye and coworkers reported the synthetic utility of the alkyne analog of a Diels-Alder reaction. An example is shown below. TMS TMS CDCI3, 26 °C, 46 h TBSO TBS 93% A [4+2] cycloaddition is believed to produce a benzyne intermediate that is quickly "trapped." Show the benzyne intermediate that would be produced in the above reaction.
3. What is the difference between the reaction conditions to obtain kinetic and thermodynamic products in the reactions of dienes?
4. Show using resonance which of the molecules below is considered an electron-donating group (EDG) and which the electron-withdrawing group (EWG): Он он vs. (a) Which dienophile above will cause a Diels-Alder reaction to proceed more rapidly with a higher yield? Briefly explain why this is the case.