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- 19.69 Propose an efficient synthesis for each of the following transformations: (a) (b) (c) Br Br -C MeO OMe22) NM₂2 in N,N-dimethylaniline ( is ortho-para director but it gives meta product in reaction with one of the following reagents. Identify the reagent. a) Br₂ b) c) HNO3 H₂SO4 O اتWhen the gum of the shrub Sterculia setigera is subjected to acidic hydrolysis, one of the water-soluble components of thehydrolysate is found to be tagatose. The following information is known about tagatose:(1) Molecular formula C6H12O6(2) Undergoes mutarotation.(3) Does not react with bromine water.(4) Reduces Tollens reagent to give d-galactonic acid and d-talonic acid.(5) Methylation of tagatose (using excess CH3 I and Ag2O) followed by acidic hydrolysis gives1,3,4,5-tetra-O-methyltagatose.(a) Draw a Fischer projection structure for the open-chain form of tagatose.(b) Draw the most stable conformation of the most stable cyclic hemiacetal form of tagatose
- 19.40 Propose an efficient synthesis for each of the following transformations: ۵-۵ ۵-۵۰ (a) (c) (e) (9) EtO. OEt می شود (b) لمه mo-od ه - هل (d) OH OH (f)Quinapril (trade name Accupril) is used to treat high blood pressure and congestive heart failure. One step in the synthesis of quinapril involves reaction of the racemic alkyl bromide A with a single enantiomer of the amino ester B. (a) What two products are formed in this reaction? (b) Given the structure of quinapril, which one of these two products is needed tosynthesize the drug?19.54 Predict the major product(s) from the treatment of acetone with the following: (d) [H], (CH3)2NH, (-H2O) (e) [H], NH2NH2, (-H2O) (f) [H], NH2OH, (-H2O) (g) NaBH4, MeOH (h) RCO3H (i) HCN, KCN (j) EtMgBr followed by H₂O (k) (C6H5)3P=CHCH2CH3 (1) LIAIH, followed by H2O
- 22.1 Which of the compounds shown below has the fewest a- hydrogens? (a) H 여 (b) (c) (d)22.35 Propose an efficient synthesis for each of the following compounds using the malonic ester synthesis: R-x (a) (d) OH OH OH Гафон (b) (c) COEF OH +2Br COEF (e)Treatment of cholesterol with mCPBA results in formation of a single epoxide A, with the stereochemistry drawn. Why isn’t the isomeric epoxide B formed to any extent?
- [ 16 ] which of following compound(s) is/are neither acetal nor hemiacetal ? он Но Он осH-CHз CHз ОН OCH3 (1) ( II ) ( III ) (IV ) (V) (a ) compounds III and V (b) compounds Il and II (c) compounds I and V (d ) compounds IV and V (e) compounds I and IV(S)-Glutamic acid is one of the 20 amino acid building blocks of polypeptides and proteins (Chapter 27). Propose a mechanism for the following conversion.Following is a retrosynthesis for the coronary vasodilator ganglefene. (a) Propose a synthesis for ganglefene from 4-hydroxybenzoic acid and 3-methyl-3-buten-2-one. (b) Is ganglefene chiral? If so, which of the possible stereoisomers are formed in this synthesis?