Concept explainers
(a)
Interpretation: The structure of C, which is formed by oxy-cope rearrangement of B with
Concept introduction: Cope rearrangement is a thermal
Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the
(b)
Interpretation: The mechanism for the conversion of C to the bicyclic alcohol D is to be drawn.
Concept introduction: Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.
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- Draw a stepwise mechanism for the Carroll rearrangement, a reaction that prepares a γ,δ-unsaturated carbonyl compound from a β-keto ester and allylic alcohol in the presence of base.arrow_forwardOne step in the synthesis of the nonsteroidal anti-inflammatory drug rofecoxib (trade name Vioxx) involves Suzuki coupling of A and B. What product is formed in this reaction?arrow_forwardConsider carbonyl compounds A–E drawn below. (a) Rank A–E in order of increasing stability. (b) Rank A–E in order of increasing amount of hydrate formed when treated with aqueous acid. (c) Which compound is most reactive in nucleophilic addition?arrow_forward
- One step in the synthesis of the nonsteroidal anti-inammatory drug rofecoxib (trade name Vioxx) involves Suzuki coupling of A and B. What product is formed in this reaction?arrow_forwardWhat is the major alkene formed when A is treated with POCl3 andpyridine? Explain why the major product is different in these reactions.arrow_forwardAddition of HCl to alkene X forms two alkyl halides Y and Z. Explain why addition of HCl occurs at the indicated C=C (called anexocyclic double bond), rather than the other C=C (called anendocyclic double bond).arrow_forward
- Treatment of α,β-unsaturated carbonyl compound X with base forms the diastereomer Y. Write a stepwise mechanism for this reaction. Explain why one stereogenic center changes conguration but the other does not.arrow_forwardAddition of HCl to alkene X forms two alkyl halides Y and Z. (A) Label Y and Z as a kinetic or thermodynamic product and explain why. (B) Explain why the addition of HCl occurs at the exocyclic C=C, rather than the other C=Carrow_forwardDienynes undergo metathesis to afford fused bicyclic ring systems. (a)Explain how A is converted to B. (b) Keeping this reaction in mind, drawthe two products formed by dienyne metathesis of C.arrow_forward
- Draw a stepwise mechanism for the conversion of lactone A to ester Busing HCl in ethanol. B is converted in one step to ethyl chrysanthemate,a useful intermediate in the synthesis of a variety of pyrethrins, naturally occurring insecticides with three-membered rings that are isolated fromchrysanthemumsarrow_forwardDimethyl cyclopropanes can be prepared by the reaction of an α, β-unsaturated carbonyl compound X with two equivalents of a Wittigreagent Y. Draw a stepwise mechanism for this reaction.arrow_forwardDraw a stepwise mechanism for the following reaction that forms ether D. D can be converted to the antidepressant fluoxetine (trade name Prozac) in a single step.arrow_forward
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