Interpretation: The product formed by
Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.
Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the
Trending nowThis is a popular solution!
Chapter 27 Solutions
Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
- 6arrow_forwardWhat product is formed when each compound undergoes thermal electrocyclic ring opening or ring closure? Label each process as conrotatory or disrotatory and clearly indicate the stereochemistry around tetrahedral stereogenic centers and double bonds.arrow_forwardAccount for the regioselectivity and stereoselectivity observed when this compound is treated with Hg(OAc)2 in H₂O Use wedge and hash bonds ONLY when needed to show reaction stereochemistry. . If the reaction produces a racemic mixture, just draw one stereoisomer.arrow_forward
- Draw the alkene that would react with the reagent given to account for the product formed. ? + H₂O H₂SO4 CH3 CH3 CHCCH3 OH CH3 • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. Sn [F ChemDoodlearrow_forwardAccount for the regioselectivity and stereoselectivity observed when this compound is treated with Br2 in H₂O by drawing the final product in the reaction. • Use wedge and hash bonds ONLY when needed to show reaction stereochemistry. • If the reaction produces a racemic mixture, just draw one stereoisomer.arrow_forwardEthylene oxide reacts readily with HO- because of the strain in the three-membered ring. Explain why cyclopropane, a compound with approximately the same amount of strain, does not react with HO-.arrow_forward
- G.133.arrow_forwardA chemist allows some pure (2S,3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide(NaOCH2CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under thesame conditions, the reaction of (2S,3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C.Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structuresof A, B, and C; give equations for their formation; and explain the stereospecificity of these reactionsarrow_forwardOptical active compound 1-chloro-3-methylcyclopentane was reacting withpotassium t-butoxide in t-butanol. Two alkene products were obtained. Themain product was optically active, and the secondary product was notoptically active. What are the two products?arrow_forward
- A chemist allows some pure (2S,3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide(NaOCH2 CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under the same conditions, the reaction of (2S,3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C. Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structures of A, B, and C; give equations for their formation; and explain the stereospecificity of these reactions.arrow_forwardWrite the products of the reaction indicating R or S stereochemistry at each center in the product. Ph. (R) catalytic HCI water solvent Phl. (R) Ph. (R) catalytic HCl water solvent Ph (S)arrow_forwardDraw the alkene that would react with the reagent given to account for the product formed. ? + H₂O H₂SO4 CH3 CH3CCH3 OH You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. Sn [F ChemDoodleⓇarrow_forward