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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.
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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_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_forwardFollowing is a retrosynthetic analysis for an intermediate in the industrial synthesis of vitamin A. (a) Addition of one mole of HCl to isoprene gives 4-chloro-2-methyl-2-butene as the major product. Propose a mechanism for this addition and account for its regioselectivity. (b) Propose a synthesis of the vitamin A precursor from this allylic chloride and ethyl acetoacetate.arrow_forward
- Sharpless epoxidation of allylic alcohol X forms compound Y. Treatment of Y with NaOH and C6H5SH in an alcohol–water mixture forms Z. Identify the structure of Y and draw a mechanism for the conversion of Y to Z. Account for the stereochemistry of the stereogenic centers in Z. Z has been used as an intermediate in the synthesis of chiral carbohydrates.arrow_forwardThe following questions concern ethyl (2-oxocyclohexane)carboxylate.(a) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by a Dieckmann cyclization.(b) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by acylation of a ketone.(c) Write structural formulas for the two most stable enol forms of ethyl (2-oxocyclohexane)carboxylate.(d) Write the three most stable resonance contributors to the most stable enolate derived from ethyl (2-oxocyclohexane)carboxylate.(e) Show how you could use ethyl (2-oxocyclohexane)carboxylate to prepare 2-methylcyclohexanone.(f) Give the structure of the product formed on treatment of ethyl (2-oxocyclohexane)-carboxylate with acrolein (H2C=CHCH=O) in ethanol in the presence of sodium ethoxidearrow_forwardGrignard reagent is a versatile tool in synthetic organic chemistry. Using bromocyclopentane as a starting material, show how a Grignard reagent, X, is synthesized. Reaction of X with water produces compound Y while treatment in carbon dioxide followed by hydrolysis forms compound Z. 3-methyl-2butanone reacts with X and hydrolyses to yield compound AA. Draw the structural formulae of compounds Y, Z and AA and write the chemical equations respectively.arrow_forward
- The UV spectrum of 1-phenylprop-2-en-1-ol shows an intense absorption at 220 nm and a weaker absorption at 258 nm. When this compound is treated with dilute sulfuric acid, it rearranges to an isomer with an intense absorption at 250 nm and a weaker absorption at 290 nm. Suggest a structure for the isomeric product and propose a mechanism for its formation.arrow_forwardSharpless epoxidation of allylic alcohol X forms compound Y. Treatment of Y with NaOH and C6H5SH in an alcohol–water mixture forms Z. Identify the structure of Y and draw a mechanism for the conversion of Y to Z. Account for the stereochemistry of the stereogenic centers in Z. Z has been used as an intermediate in the synthesis of chiral carbohydrates.arrow_forwardAn alkene is treated with OsO4 followed by H2O2. When the resulting diol is treated with HIO4, the only product obtained is an unsubstituted cyclic ketone with molecular formula C6H10O. What is the structure of the alkene?arrow_forward
- Describe how 3-methyl-1-phenyl-3-pentanol can be prepared from benzene. You can use any inorganic reagents and solvents, and any organic reagents provided they contain no more than two carbons.arrow_forwardThe following substances can be prepared by a nucleophilic addition reaction between an aldehyde or ketoneand a nucleophile. Identify the reactants from which they were prepared. If the substance is an acetal, identifythe carbonyl compound and the alcohol; if it is an imine or enamine, identify the carbonyl compound and theamine. You do not have to consider stereochemistry. In cases where there is more than one answer, just giveone. Use Grignard reagents when an organometallic reagent is required. Draw the Grignard reagent as acovalent magnesium bromide.arrow_forwardIsoerythrogenic acid, C18H26O2, is an acetylic fatty acid that turns a vivid blue on exposure to UV light. On Catalytic hydrogenation over a palladium catalyst, five molar equivalents of hydrogen are absorbed, and stearic acid, CH3(CH2)16CO2H, is produced. Ozonolysis of isoerythrogenic acid yields the following products: formaldehyde, CH2O, malonic acid, HO2CCH2CO2H, adipic acid, HO2C(CH2)4CO2H, and the aldehyde carboxylic acid, OHC(CH2)6CO2H. Provide a structure for isoerythrogenic acid.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
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