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- 4. (a) Outline the steps in the following transformation with corresponding structures : H?ICH1or C6H100 -H* Tautomerism Adipic acid Oxydation C6H100Following 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?When 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
- PQ-22. Which structure is a reasonable intermediate in the acid-catalyzed hydrolysis of ethyl acetate, shown, in dilute aqueous acid? O O (A) H3C-C-OCH₂CH3 OH OH₂ (C) H3C-C-OCH₂CH3 H OH (B) H3C-C-OCH₂CH3 OH2 O (D) H3C-CPredict the products formed when limonene reacts with the followingreagents.(a) excess HBr (b) excess HBr, peroxides (c) excess Br2 in CCl4(d) ozone, followed by dimethyl sulfide (e) warm, concentrated KMnO4 (f) BH3 # THF, followed bybasic H2O2Which one of the following statements best describes the chemistry of ring A? E B OH он, A H Oleandrin is a toxic cardiac glycoside found in the poisonous plant, oleander (Nerium oleander L). It has a very long IUPAC name: acetic acid [(35,5R, 10S,13R,14S, 16S, 17'R)-14-hydroxy-3-[[(2R,4S,5S,65)-5-hydroxy-4-methoxy-6-methyl- 2-tetrahydropyranyl]oxy]-10,13-dimethyl-17-(5-oxo-2H-furan-3-y)-1,2,3,4,5,6,7,8,9,11,12,15,16,17- tetradecahydrocyclopenta[a]phenanthren-16-yl] ester Ring-A can act as a reducing sugar Ring-A can undergo mutarotation Ring-A is non-reducing O Ring-A is a furanose
- Which ester can be easily condensed with NaOEt to produce B-keto ester salt? (A) Ph-C–OEt (B) СH, CH, ҫ OEt (C) CH;-CH-Ç-OEt (D) CH, 0 Ҫ Н CH; ÖDraw the structure of the products that will be formed when aniline reacts with nitrous acid at 5oC, followed by: (e) H3PO4, H2O(f) Cu2O, Cu2+, H2O2. Compound A, C;H100 , is one of the basic building blocks of nature. All steroids and many other naturally occuring compounds are built from compound A. Spectroscopic analysis of A yields the following information: IR: 3400 cm-'; 1640 cım- IH NMR: 1.63 & (3 H, singlet); 1.70 ô (3 H, singlet); 3.83 6 (1 H, broad singlet); 4.15 8 (2 H, doublet, j = 7 Hz); 5.70 ô (1 H, triplet, ) = 7 Hz) (a) How many double bonds and/or rings does A have? (b) From the IR spectrum, what is the identity of the oxygen-containing functional group? (c) What kinds of protons are responsible for the NMR absorptions listed ? (d) Propose a structure for A.
- d-Glucuronic acid is found widely in plants and animals. One of its functions is to detoxify poisonous HO-containing compoundsby reacting with them in the liver to form glucuronides. Glucuronides are water soluble and therefore readily excreted. Afteringestion of a poison such as turpentine or phenol, the glucuronides of these compounds are found in the urine. Draw thestructure of the a- and b-glucuronides formed by the reaction of b-d-glucuronic acid and phenol.[ 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(a) Explain how NaBH4 in CH3OH can reduce hemiacetal A to butane-1,4-diol (HOCH2CH2CH2CH2OH). (b) What product is formed when A is treated with Ph3P = CHCH2CH(CH3)2? (c) The drug isotretinoin is formed by reaction of X and Y. What is the structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it is dispensed under strict controls because it also causes birth defects.
