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Chapter 9 Solutions
ORGANIC CHEMISTRY
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General Chemistry: Principles and Modern Applications (11th Edition)
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Chemistry & Chemical Reactivity
- 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_forward4. 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_forward
- Dihydropyran 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_forwardlo CI H3C H3C 07 ↔X + :0: OH Dimethylaminopyridine (DMAP) is often used as a catalyst in esterification reactions. A basic solvent such as triethylamine is used to react with the liberated proton from the alcohol group. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CI NMe₂ N(CH₂CH3)3 CH3 6--10-- NMe2arrow_forwardReaction 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_forward
- Identify the reagents needed to carry out each reaction. HBr Br KOC(CH3)3 OH TSCI pyridine OTS TSOH Br NaH NBS H20 |Cl, HO Br "OH CIarrow_forwardPredict the major product for each reaction. i NaOEt A KOH Δ NaOH Aarrow_forwardWhen 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_forward
- Choose the best reagents to complete the reaction shown below. OH 00 OH OH Q Q A B C D NaOH LiF H₂O NaHarrow_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
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