Concept explainers
The sex attractant of the female winter moth has been identified as the tetraene
hexadecadien
ol and allyl alcohol.
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Chapter 18 Solutions
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- Ethylene oxide is the starting material for the synthesis of 1,4-dioxane. Propose a mechanism for each step in this synthesis.arrow_forwardA 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_forwardDihydropyran is synthesized by treating tetrahydrofurfuryl alcohol with an arenesulfonic acid, ArSO3H. Propose a mechanism for this conversion.arrow_forward
- Knoevenagel condensation is a reaction involving an active methylene compound (a CH2 flanked by two electron-withdrawing groups) and an aldehyde and ketone. Propose a mechanism for the reaction below.arrow_forwardWhen cis-4-chlorocyclohexanol is treated with sodium hydroxide in ethanol, it gives mainly the substitution product trans-1,4-cyclohexanediol (1). Under the same reaction conditions, trans-4-chlorocyclohexanol gives 3-cyclohexenol (2) and the bicyclic ether (3). (a) Propose a mechanism for formation of product (1), and account for its configuration. (b) Propose a mechanism for formation of product (2). (c) Account for the fact that the bicyclic ether (3) is formed from the trans isomer but not from the cis isomer.arrow_forwardHydroboration of 2-methyl-2-pentene at 25°C, followed by oxidation with alkaline H2o2, yields 2-methyl-3-pentanol, but hydroboration at 160°C followed by oxidation yields 4-methyl-1-pentanol. Suggest a mechanism.arrow_forward
- We are asked to prepare (CH3)2CHCH2OH (2- methylpropan-1-ol) from an alkyl halide and any required reagents ?arrow_forwardExplain how the reaction of (CH3)2CHCH(Cl)CH3 with H2O yields two substitutionproducts, (CH3)2CHCH(OH)CH3 and (CH3)2C(OH)CH2CH3arrow_forwardCapsaicin, the spicy component of hot peppers, can be prepared from amine X and acid chloride Y. Devise a synthesis of Y from (E)-6-methylhept-4-en-1-ol [(CH3)2CHCH=CH(CH2)3OH], CH2(CO2Et)2, and any required inorganic reagents.arrow_forward
- When 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_forwardBoron tribromide (BBr3) cleaves ethers to give alkyl halides and alcohols.R¬O¬R′ + BBr3 ¡ R¬O¬BBr2 + R′BrR¬O¬BBr2 + 3 H2O ¡ ROH + B(OH)3 + 2 HBrThe reaction is thought to involve attack by a bromide ion on the Lewis acid–base adductof the ether with BBr3 (a strong Lewis acid). Propose a mechanism for the reaction ofbutyl methyl ether with BBr3 to give (after hydrolysis) butan-1-ol and bromomethane.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning