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- One of the later steps in glucose biosynthesis is the isomerization of fructose 6-phosphate to glucose 6-phosphate. Propose a mechanism, using acid or base catalysis as needed.The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.40) Give the product for the following reaction. CH₂CH₂- -H HON
- D-glucose can form two isomers of glucosides after reaction with methanol in presence of catalytic HCI as shown below. Suggest a mechanism for the following reaction. CH2OH CH,OH CH2OH HO CH;OH но HO но но. но OCH3 HČI HO. OH ÓCH3 OH онRing-A is considered a deoxy-pyranoside because it is missing an alcohol functional group on which carbon of ring-A? Use standard carbohydrate numbering. E в он он 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,6S)-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 B.Draw a stepwise mechanism for the acid-catalyzed interconversion of two glucose anomers by mutarotation. HO- HO- но но Но HO OH OH Но OH
- If the following molecule cyclized, which of the following statements would be true? H- HO HO H- CHO -OH H H -OH CH₂OH A five membered ring would be formed Mannopyranose would form Hemiketal chemistry would result from the C5-OH doing nucleophilic attack of the carbonyl carbon This cyclized sugar could be amide linked to a sphingosine as part of formation of sphingomyelin This cyclized sugar could modify a cerebrosideComplete the following retrosynthesis. A 1 B 2 C 3 ☑ 4 میں OH L 2 OH OH ? 3 "우 HO Your answer + CH3OHPropose a mechanism for the lactone formation HO OH NEt3 pyridine (catalytique)
- H₂C OEt H₂C OEt 1. NaOEt, EtOH 2. H₂O* H₂C EtOH OEt Esters, like aldehydes and ketones, are weakly acidic. Treatment of an ester with 1 equivalent of a strong base, such as sodium ethoxide, causes a reversible carbonyl condensation to occur that forms a ẞ-ketoester. This reaction is known as the Claisen condensation. The tetrahedral intermediate thus formed expels an alkoxide leaving group to give an acyl substitution product, a ẞ-ketoester. The steps leading up to this point are all reversible. The best yields for the Claisen condensation are obtained when the starting ester has more than one acidic a-hydrogen. In these cases, a second deprotonation of the a-carbon drives the reaction equilibrium toward the product, thus requiring a full equivalent of base instead of a catalytic amount. Subsequent protonation with dilute aqueous acid resultsn a high yield of the final product. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing…21-25 Draw the major organic product of the reactions4. Draw the organic products of the reactions of (R)-2-iodobutane with azide ion and methanol. Draw allstereoisomers expected to form. (R)-2-iodobutane Na*N3* CH3OH