Concept explainers
Interpretation: For the given reaction, structures of compounds A, B, C, and D need to be drawn.
Concept Introduction: Grignard reagent can act as a strong base as well as a strong nucleophile. The nature of the reaction depends on the reactant that is if the possibility of an attack of nucleophile or elimination is more. In the case of
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- A key step in the synthesis of β-vetivone, a major constituent of vetiver, a perennial grass found in tropical and subtropical regions of the world, involved the reaction of compound A and dihalide B with two equivalents of LDA to form C. Draw a stepwise mechanism for this reaction. β-Vetivone contains a spiro ring system—that is, two rings that share a single carbon atom.arrow_forwardMuscalure, the sex pheromone of the common housefly, can be prepared by a reaction sequence that uses two nucleophilic substitutions. Identify compounds A–D in the following synthesis of muscalure.arrow_forwardIbufenac, a para-disubstituted arene with the structure HO2CCH2C6H4CH2CH(CH3)2, is a much more potent analgesic than aspirin, but it was never sold commercially because it caused liver toxicity in some clinical trials. Devise a synthesis of ibufenac from benzene and organic halides having fewer than five carbons.arrow_forward
- Muscalure, the sex pheromone of the common housefly, can be preparedby a reaction sequence that uses two nucleophilic substitutions. Identifycompounds A–D in the following synthesis of muscalure.arrow_forwardIdentify compound A to E.arrow_forwardIbufenac, a para-disubstituted arene with the structureHO2CCH2C6H4CH2CH(CH3)2 , is a much more potent analgesic thanaspirin, but it was never sold commercially because it caused livertoxicity in some clinical trials. Devise a synthesis of ibufenac frombenzene and organic halides having fewer than five carbons.arrow_forward
- Draw a stepwise mechanism for the following reactions, two steps in R. B. Woodward’s classic synthesis of reserpine in 1958. Reserpine, which is isolated from the extracts of the Indian snakeroot Rauwola serpentina Benth, was used at one time to manage mild hypertension associated with anxiety.arrow_forwardDraw a stepwise mechanism for the following reactions, two steps in R. B. Woodward’s classic synthesis of reserpine in 1958. Reserpine, which is isolated from the extracts of the Indian snakeroot Rauwolfia serpentina Benth, was used at one time to manage mild hypertension associated with anxiety.arrow_forwardWhat neutral nucleophile is needed to convert dihalide A to ticlopidine, an antiplatelet drug used to reduce the risk of strokes?arrow_forward
- Aprepitant (trade name Emend) is used to prevent the acute nausea and vomiting caused by chemotherapy. Identify E and F, intermediates in the synthesis of aprepitant.arrow_forwardThe compound eutypine is an antibacterial agent isolated from the fungus Eutypa lata. This fungus results in a disease common to vineyards called eutyposis. Give a sequence of reactions that will take the following reactant and give eutypine when the other reactants used in the sequence are acetylene and acetone.arrow_forwardNicotinic acid, more commonly named niacin, is one of the B vitamins. Show how nicotinic acid can be converted to (a) ethyl nicotinate and then to (b) nicotinamide.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning