20.44 The Diels-Alder reaction is not limited to making six-membered rings with only car- bon atoms. Predict the products of the following reactions that produce rings with atoms other than carbon in them. OCCH OCCH H (b) CH C(CH₂)s COOCH མ་ནས་བ (c) N=C H -0.X- (e) H C=N COOCHS + CH2=CHCH₂ →→

20.44 The Diels-Alder reaction is not limited to making six-membered rings with only car- bon atoms. Predict the products of the following reactions that produce rings with atoms other than carbon in them. OCCH OCCH H (b) CH C(CH₂)s COOCH མ་ནས་བ (c) N=C H -0.X- (e) H C=N COOCHS + CH2=CHCH₂ →→

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.35P: The following triene undergoes an intramolecular Diels-Alder reaction to give a bicyclic product....

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Similar questions

3. Which is the first step in the mechanism of this reaction? H₂O/H3O+ (A) (B) (D) (A) || (B) || + H-OH 24. What reagents would make this product from a Diels-Alder reaction? + H-OH H-OH₂ H-OH₂ La CI Qa CI HO: H₂O HO: H₂O CI CI
The following triene undergoes an intramolecular Diels-Alder reaction to give a bicyclic product. Propose a structural formula for the product. Account for the observation that the Diels-Alder reaction given in this problem takes place under milder conditions (at lower temperature) than the analogous Diels-Alder reaction shown in Problem 20.34.
21. (a) Predict the product of the following Diels-Alder reaction( Show the correct stereochemistry for the product). cyclopentadiene + cis 1,2-dicyanoethylene (NC-CH=CH-CN) -------> (b) Show the mechanism for the reaction in(a) above.
5) Propose a synthesis of each of the following molecules by Diels-Alder reactions. CH, ọ a) CN CN b) { c) CH3 OCH3 OCH₂
The following are several isomers of C10H14 with two fused six-membered rings. A B D E G H (a) Identify which will react with ethene in a Diels-Alder reaction and which will not. (b) Draw one more isomer with two fused six-membered rings that will react with ethene in a Diels-Alder reaction.
PQ-21. From the standpoint of reactivity, which is the poorest dienophile to react with 2,3-dimethyl-1,3-butadiene in a Diels-Alder reaction? H (A) CO2CH3 (B) (C) (D) CN
The diene lactone shown in part (a) has one electron-donating group (¬OR) and one electron-withdrawing group(C“O). This diene lactone is sufficiently electron-rich to serve as the diene in a Diels–Alder reaction.(a) What product would you expect to form when this diene reacts with methyl acetylenecarboxylate, a strong dienophile?
Cyclopentadienyl anion (shown) has the following characteristic. O it is an anion with six π electrons, meeting the Hückel rule for aromaticity O it is not aromatic because it has only four electrons and the tetrahedral carbon prevents cyclic conjugation O it is an anion with six electrons, meeting the Hückel rule for anti-aromaticity O it is an anion with four electrons, meeting the Hückel rule for aromaticity
Can you answer the question and explain it? With the mechanism Only a and b
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
Reaction of this bicycloalkene with bromine in carbon tetrachloride gives a trans dibro- mide. In both (a) and (b), the bromine atoms are trans to each other. However, only one of these products is formed. CH3 CH3 CH3 Br Br CH,Cl, + Br2 or Br Br (a) (b) Which trans dibromide is formed? How do you account for the fact that it is formed to the exclusion of the other trans dibromide?
Please draw out the structures of compound A, B, C, D and E. The formula of Compound A is C5H6. Compound A react with 2 equivalent of Br2 to produce product B; Compound A was oxidized with KMN04 to give two carboxylic acids C and D. Compound A can undergo Diels-Alder reaction with maleic anhydride to produce compound E.