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Capsaicin, the spicy component of hot peppers, can be prepared from
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ORGANIC CHEMISTRY (LOOSELEAF) >CUSTOM<
- A step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Propose a mechanism for formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. Alprostadil is used as a temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.arrow_forwardCembrene, C20H32, is a diterpenoid hydrocarbon isolated from pine resin. Cembrene has a UV absorption at 245 nm, but dihydrocembrene (C20H34), the product of hydrogenation with 1 equivalent of H2, has no UV absorption. On exhaustive hydrogenation, 4 equivalents of H2 react, and octahydrocembrene, C20H40, is produced. On ozonolysis of cembrene, followed by treatment of the ozonide with zinc, four carbonylcontaining products are obtained: Propose a structure for cembrene that is consistent with its formation from geranylgeranyl diphosphate.arrow_forwardWhat product is obtained from the reaction of excess benzene with 1-chloro-2,2-dimethylpropane + AlCl3 ?arrow_forward
- The sex attractant of the female winter moth has been identified as the tetraene CH3(CH2)8CH=CHCH2CH=CHCH2CH=CHCH=CH2. Devise a synthesis of this material from 3,6-hexadecadien-1-ol and allyl alcohol.arrow_forwardWhen 1-butanol is treated with conc. H2SO4 and heat .A product 'A' is formed from the reaction. Treatment of 'A' with HCl/H2O gives 'B'. Treatment of 'A' with cold KMnO4/OH- gives 'C' Treatment of 'A' with hot KMnO4 /OH- gives 'D' followed by acidification of the mixture to give 'E' 1. identify the compounds represented by A,B,C,D and E.arrow_forwardDevise a synthesis of 1-phenyl-5-methylhexane [C6H5(CH2)4CH(CH3)2] from acetylene, alkyl halides, and any required inorganic reagents.arrow_forward
- Draw the organic products formed when cyclopentene is treated with each reagent. With some reagents, no reactionoccurs.a. H2 + Pd-Cb. H2 + Lindlar catalystc. Na, NH3d. CH3CO3He. [1] CH3CO3H; [2] H2O, HO–f. [1] OsO4 + NMO; [2] NaHSO3, H2Og. KMnO4, H2O, HO–h. [1] LiAlH4; [2] H2Oi. [1] O3; [2] CH3SCH3j. (CH3)3COOH, Ti[OCH(CH3)2]4, (–)-DETk. mCPBAl. Product in (k); then [1] LiAlH4; [2] H2Oarrow_forwardPropose a synthesis to convert 1-methylcyclopentene B to the cyclic ester C. Show all intermediates, and reagents necessary for each step.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning