Acid-catalyzed hydrolysis of the following epoxide gives a trans diol. CH3 CH3 CH3 НО, НО, H,SO, + H,O HO HO Only this glycol This glycol is is formed. not formed. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?
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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.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.Ethylene oxide is the starting material for the synthesis of 1,4-dioxane. Propose a mechanism for each step in this synthesis.
- Treatment of 1-aminoadamantane, C10H17N, with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, R3N, involves two successive SN2 reactions and gives compound A. Propose a structural formula for compound A.Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to E. (d) Propose a mechanism for the conversion of F to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?When cis-2-decalone is dissolved in ether containing a trace of HCl, an equilibrium is established with trans-2-decalone. The latter ketone predominates in the equilibrium mixture. Propose a mechanism for this isomerization and account for the fact that the trans isomer predominates at equilibrium.
- An acetal produces the following three compounds upon hydrolysis. Of acetals A-E which could it be? H3CO OCH3 П A B U D Acetal A H2O H₂SO4(cat.) замен поста "OCH3 В + HO. H₂CO ОН D + OCH3 CH3OH E OCH3 "OCH3HN O= NH allobarbital This barbiturate can be synthesized in three steps from diethyl malonate: 1 & 2. Diethyl malonate reacts successively with two alkyl bromides in Na+ OEt; 3. The dialkylated intermediate is treated with urea to form the final product. Draw the structures of the two alkyl bromides that must be used to synthesize this barbiturate. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. Sn [1H3C. H3C. CH3 nnc» XT :OH 2 CH₂OH HCI catalyst Aldehydes and ketones react reversibly with two equivalents of alcohol in the presence of an acid catalyst to give acetals. Alcohols are poor nucleophiles, and so protonation of the carbonyl oxygen is used to make the carbonyl carbon a stronger electrophile. Addition of the first equivalent of alcohol gives a hemiacetal, a hydroxyether. Addition of the second equivalent of alcohol is accompanied by loss of water to yield the product acetal. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 H3C CH3OH H3CQ OCH3 CH3 H3C. H HO: :OCH 3 CH3 46
- H3C OH OH H+ CH3 Esters can be synthesized by an acid-catalyzed nucleophilic acyl substitution between an alcohol and a carboxylic acid; this process is called the Fischer esterification reaction. Because the alcohol oxygen is a poor nucleophile, the carbonyl carbon is made a better electrophile by protonation of the carbonyl oxygen. The steps of the synthesis are all reversible. The reaction is generally driven to completion by using an excess of the liquid alcohol as a solvent, or by distilling off the product as it forms. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CIX 10-4 H₂O CH3 H₂O CH3Hemiacetals are formed by nucleophilic addition of a hydroxyl group to a carbonyl group. In the same way, cyclic hemiacetals can be formed by treating aldehyde with a catalytic amount of an acid. For the reaction below, draw the structure of the hemiacetal and write the possible mechanism for the transformation. H2SO4 но HEnamines normally react with methyl iodide to give two products: one arising from alkylation at nitrogen and the second arising from alkylation at carbon. For example, 8-18-8-8. CH,I 25°C CH3 reflux CH3 CH3 Product of Product of (racemic) Galkylation Nalkylation Heating the mixture of C-alkylation and N-alkylation products gives only the product from C-alkylation. Propose a mechanism for this isomerization.