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- 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.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 онIf 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 cerebroside
- Draw a stepwise mechanism for the acid-catalyzed interconversion of two glucose anomers by mutarotation. HO- HO- но но Но HO OH OH Но OH40) Give the product for the following reaction. CH₂CH₂- -H HONRing-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.
- Propose 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…Complete the following retrosynthesis. A 1 B 2 C 3 ☑ 4 میں OH L 2 OH OH ? 3 "우 HO Your answer + CH3OH
- 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* CH3OHCH2–0–C–C 17H37 What will be the complete hydrolysis products of the given structure below? CH2–0–Ċ–C17H37 HC–0–C–C17H29 of 0=P-0–CH2CH2N CH3)3 O yield 1 mole of fatty acid, sphingosine, phosphoric acid & choline upon hydrolysis O yield 1 mole of fatty acid, glycerol, phosphoric acid & choline upon hydrolysis yield 2 moles of fatty acid and 1 mole of sphingosine, phosphoric acid & choline upon hydrolysis O yield 2 moles of fatty acid and 1 mole of glycerol, phosphoric acid & choline upon hydrolysis
