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Using the Woodward–Hoffmann rules, predict the stereochemistry of below
reaction.
a thermal [5,5] sigmatropic rearrangement
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- Using the Woodward–Hoffmann rules, predict the stereochemistry of belowreaction. a [6 + 4] thermal cycloadditionA solution of 5-methylcyclopenta-1,3-diene rearranges at roomtemperature to a mixture containing 1-methyl-, 2-methyl-, and 5-methylcyclopenta-1,3-diene. (a) Show how both isomeric products areformed from the starting material by a sigmatropic rearrangementinvolving a C–H bond. (b) Explain why 2-methylcyclopenta-1,3-diene isnot formed directly from 5-methylcyclopenta-1,3-diene by a [1,3]rearrangement.The bicyclic alkene P can be prepared by thermal electrocyclic ringclosure from cyclodecadiene Q or by photochemical electrocyclic ringclosure from cyclodecadiene R. Draw the structures of Q and R, andindicate the stereochemistry of the process by which each reactionoccurs.
- In 4+2 cycloaddition, ENDO stereochemistry is preferred because: endo stereochemistry allows the diene to adopt s-cis conformation. endo stereochemistry results in less steric hindrance. the transition state leading to endo stereochemistry is higher energy. it allows for additional π to π overlap between the diene and the dienophile.Using the Woodward–Hoffmann rules, predict the stereochemistry of eachreaction.a. a [6 + 4] thermal cycloadditionb. photochemical electrocyclic ring closure of deca-1,3,5,7,9-pentaenec. a [4 + 4] photochemical cycloadditiond. a thermal [5,5] sigmatropic rearrangementOne step in the synthesis of dodecahedrane (Section 4.11) involves reaction of the tetraene C with dimethylacetylene dicarboxylate (D) to afford two compounds having molecular formula C16H16O4. This reaction has been called a domino Diels–Alder reaction. Identify the two products formed.
- Draw the product formed when diene M undergoes disrotatory cyclization. Indicate the stereochemistry at new sp3 hybridized carbons. Will the reaction occur under thermal or photochemical conditions?One step in the synthesis of dodecahedrane involves reaction of the tetraene C with dimethylacetylene dicarboxylate (D) to afford two compounds having molecular formula C16H16O4. This reaction has been called a domino Diels–Alder reaction. Identify the two products formed.Using one or more of the following compounds as starting materials or products illustrate, with an example, each of the following type of pericyclic reactions. Your answer should include curved arrow mechanisms. (i) a disrotatory thermal electrocyclic reaction (ii) a conrotatory photochemical electrocyclic reaction (iii) a [4+2] cycloaddition (iv) a [3,3]-sigmatropic rearrangement
- Predict the stereochemistry of the following Pericyclic reactions a) a thermal [2 + 6] cycloaddition b) photochemical [3 ,6] sigmatropic rearrangementTwo products are formed in the following [1,7] sigmatropic rearrangement, one due to hydrogen migration and the other to deuterium migration. Showthe configuration of the products by replacing A and B with the appropriate atoms (H or D).C(CH3)3X +H20 where (X-F, CI, Br, I) give reaction with each of halogen as well determine with which halogen substitution reaction is more favorable and feasible and give reason of its feasibility? C(CH3)3OH