(ii) Suggest a synthesis of ketone 6 from (E)-3,4-(dimethoxy)cinnamic acid 9. You can assume that any other reagents will be made available to you. MeO MeO 9 CO₂H steps MeO MeO 6
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- Choose the required reagents necessary to prepare the following compound in the presence of catalytic aqueous acid. NH MeNH, CH3CaO D B A STRUCTURE A STRUCTURE B STRUCTURE C O STRUCTURE D C 20 ptsAcid-catalyzed hydrolysis of the following epoxide gives a trans diol. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?In Problem 7.28, we saw this two-step sequence in Johnsons synthesis of the steroid hormone progesterone. Propose a structural formula for the intermediate formed in Step 3 and a mechanism for its conversion in Step 4 to progesterone.
- 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.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.
- Treatment of an aldehyde or ketone with cyanide ion (-:C=N), followed by protonation of the tetrahedral alkoxide ion intermediate, gives a cyanohydrin. Show the structure of the cyanohydrin obtained from cyclohexanone.Amino acids can be prepared by reaction of alkyl halides with diethyl acetamidomalonate, followed by heating the initial alkylation product with aqueous HCl. Show how you would prepare alanine, CH3CH(NH2)CO2H, one of the twenty amino acids found in proteins, and propose a mechanism for acid-catalyzed conversion of the initial alkylation product to the amino acid.In the presence of a trace of acid, d@hydroxyvaleric acid forms a cyclic ester (lactone).HO¬CH2CH2CH2CH2¬COOHd@hydroxyvaleric acid(a) Give the structure of the lactone, called d@valerolactone.(b) Propose a mechanism for the formation of d@valerolactone.
- 4 Which of the following alcohols could not be made selectively by hydroboration-oxidation of an alkene? Explain. about the (b) (a) (c) OH | CH3CH₂CH₂CHCH3 In H OH (CH3)2CHC(CH3)2 (d) CH3 vino zbiory 1 OH o no atou OH vollot edt evig H noituloa siblos V H но но CHO SHO=3₂HƆ m² CH3s 10 out of ST bewollot giaylonoso no WBTⱭ 12-8 His to edustrie 5 wode, $2-8 OnMX dilw osviel vitabDevise a synthesis of the ketone hexan-3-one, CH3CH2COCH2CH2CH3, from CH3CH2Br as the only organic starting material; that is, all the carbon atoms in hexan-3-one must come from CH3CH2Br. You may use any other neededreagents.6B. Write a reaction scheme to selectively synthesize the following: OH OMe H3C OMe
