Question 6 (12 points) Using arrow-pushing mechanisms, show how Diels-Alder reactions can be used to form the following products. a) b) c) d) OEt H HO H CI CI OEt Ο
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In this case, the diene is 1,3-butadiene and the dienophile is ethyl acrylate. Show more…
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7. Which of the following dienes would work in a Diels-Alder [4+2] cycloaddition as the 4e- diene? 8. Predict the major product for the following Diels-Alder reactions:
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[4 + 2) Cycloadditions with o-quinones such as $\textbf{B}$ are often complex because a variety of products are possible. a. Draw arrows to illustrate how each product is formed when $\textbf{B}$ reacts with styrene, and label the "diene" and "dienophile" components. b. Draw arrows to illustrate how each product is formed when $\textbf{B}$ reacts with 1,3-butadiene, and label the "diene" and "dienophile" components. c. $o$-Quinone $\textbf{C}$ reacts with diene $\textbf{D}$ to form heterocycle $\textbf{E}$ by a process that involves a cycloaddition followed by a [3,3) sigmatropic rearrangement. Use curved arrows to illustrate how this two-step sequence occurs. $\textbf{E}$ is $not$ formed directly from $\textbf{C}$ by a Dials$-$Alder reaction.
Pericyclic Reactions
Summary of Rules for Pericyclic Reactions
REACTIONS: Give the MAJOR organic products of each of the following reactions. Indicate stereochemistry of the products where appropriate. [7 points] a) H3C, H3C (epoxide) H, H + CH3CH2OH / H2SO4 b) cyclopentyl methyl ether + HBr (2 eq) c) 2-hexanol + SOCl2 / pyridine d) H3C, H3C (epoxide) H, H + 1) NaOCH3 2) H2O e) 2-methylcyclohexanol + 1) TsCl, pyridine 2) KOtBu f) 3-methyl-4-hexanol + PBr3 g) 2-ethylcyclohexanol + 1) NaH 2) CH3CH2I
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