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Organic Chemistry
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- Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardHow would you synthesize the following compounds from cyclohexanone? a) 1Methylcyclohexene b) 2Phenvlcyclohexanone c) cis1, 2Cyclohexanediol d) 1Cyclohexylcyclohexanolarrow_forwardThe Favorskiireaction involves treatment of an a-bromo ketone with base to yield a ring-contracted product. For example, reaction of 2-bromocyclohexanone with aqueous NaOH yields cyclopentanecarboxylic acid.what is the mechanism of the reaction.arrow_forward
- 4. Arrange the following phenols in terms of increasing acidity beginning with the least acidic: OH A Answer: ОН NHCH3 в ОН CN C CH₂OH Н D ОН зов CH3 E ОН CO₂Me Farrow_forwardDihydropyran is synthesized by treating tetrahydrofurfuryl alcohol with an arenesul- fonic acid, ARSO,H. Propose a mechanism for this conversion. ARSO,H OH + H,O Tetrahydrofurfuryl Dihydropyran alcoholarrow_forwardTreatment of trans-2-chlorocyclohexanol with NaOH yields 1, 2-epoxy-cyclohexane, but reaction of the cis isomer under the same conditions yields cyclohexanone. Propose mechanisms for both reactions, and explain why the different results are obtained.arrow_forward
- Reaction of phenol with acetone in the presence of an acid catalyst gives a compound known as bisphenol A, which is used in the production of epoxy and polycarbonate resins Propose a mechanism for the formation of bisphenol A. OH H;PO, + H,O НО HO Phenol Acetone Bisphenol Aarrow_forwardChoose the best reagents to complete the reaction shown below. OH 00 OH OH Q Q A B C D NaOH LiF H₂O NaHarrow_forwardPredict the major product for each reaction. i NaOEt A KOH Δ NaOH Aarrow_forward
- When cis-2-decalone is dissolved in ether containing a trace of HCI, an equilibrium is established with trans-2-decalone. The latter ketone predominates in the equilibrium mixture. H H HCI cis-2-Decalone trans-2-Decalone Propose a mechanism for this isomerization and account for the fact that the trans iso- mer predominates at equilibrium.arrow_forwardThe 1H and 13C NMR spectra below belong to a compound with formula C6H10O2. Propose a structure for this compound.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_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning