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- Provide a mechanism for the following transformation: CrO3 но, H30*Treating 2-methylpropene with methanol in the presence of sulfuric acid gives tert-butyl methyl ether. CH3 CH3 H,SO, CH,C=CH, + CH,OH CH,C-OCH, ČH3 Propose a mechanism for the formation of this ether.Cyclohexene can be converted to 1-cyclopentenecarbaldehyde by the following series of reactions. СНО HIO, CH12O2 OsO, base 1-Cyclopentenecarbaldehyde Propose a structural formula for each intermediate compound.
- Amantadine is effective in preventing infections caused by the influenza A virus and in treating established illnesses. It is thought to block a late stage in the assembly of the virus. Amantadine is synthesized by treating 1-bromoadamantane with acetonitrile in sulfuric acid to give N-adamantylacetamide, which is then converted to amantadine. CH,C=N in H,SO, Br NHCCH3 NH2 1-Bromoadamantane Amantadine (a) Propose a mechanism for the transformation in Step 1. (b) Describe experimental conditions to bring about Step 2.10. Propose the mechanism for the following transformation: omy-of ww2) How would you synthesize the following compounds from cyclohexanone? CH₂Br A Br B CH₂C6H5 D CH2CH2CO2H
- 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 alcoholOptically active butan-2-ol racemizes in dilute acid. Propose a mechanism for this racemization.Ethylene oxide is the starting material for the synthesis of 1,4-dioxane. Propose a mechanism for each step in this synthesis.
- Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.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.Dihydropyran is synthesized by treating tetrahydrofurfuryl alcohol with an arenesulfonic acid, ArSO3H. Propose a mechanism for this conversion.
