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Interpretation:
The possible mechanism for the formation of heterocyclic base on protected ribosylamine on the reaction with
Concept introduction:
舧 Electrophiles are electron-deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair.
舧 Nucleophiles are electron-rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair.
舧 A nucleoside consists of a nucleobase (also termed as nitrogenous base) and a five-carbon sugar (either ribose or deoxyribose).
舧 A
舧 In a nucleoside, the anomeric carbon is linked through a glycosidic bond to the N9 of a purine or N1 of a pyrimidine.
舧 Examples of nucleosides include cytidine, uridine, adenosine, guanosine and thymidine.
舧 Sugar (ribose/deoxyribose) and nitrogenous bases are linked through N-glycosidic bonds.
舧 These glycosidic bonds are formed by condensation reaction of first carbon of sugar molecule with the nitrogen atom
舧 This particular glycosidic bond is stable in basic solutions, but readily hydrolyzes in the presence of acids.
舧 Uridine ribonucleoside can be synthesized by the reaction of protected ribosylamine with
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Chapter 25 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
- In addition to the reactions mentioned in, PLP can catalyze beta-substitution reactions. Propose a mechanism for the following PLP-catalyzed beta-substitution reaction:arrow_forwardConsidering the possible thiocyanate resonance structures, draw the chemical structure of another possible nucleophilic aromatic substitution product of thiocyanate with 2,4-dinitrobromobenzene.arrow_forwardWhat is the product of the starting material D-glyceraldehyde which will (1) produce aldaric acid upon reacting with HNO3 + H2O, NaOCH2, NH2OH, and (CH3CO)2O + NaOCOCH3 (2) produce tartaric acid upon reacting with HNO3 + H2O, NaOCH3, NH2OH, and (CH3CO)2O + NaOCOCH3arrow_forward
- . Name and Draw the structures of all possible chemical (Electrophilic aromatic substitution) reactions of the p- aminophenol; Friedal Craft Alkylation Friedal Craft Acylation Is p- aminophenol undergose this reaction?arrow_forwardOn the basis of the general mechanism for acid-catalyzed ester hydrolysis shown in Mechanism 20.2, write an analogous sequence of steps for the specific case of ethyl benzoate hydrolysis.arrow_forwardGive steucture of organic and inorganic products of the following sn2 reaction, and identify the nucleophile, substrate, and leaving group.arrow_forward
- What is the product/s when Asetone is allowed to react with KMno4, H2O, NaOH while being heated in the presence of HCl. is there any sereochemistry associated with this reactionarrow_forwardBy using either Suzuki-Miyaura coupling reaction or Heck coupling reaction, suggest a synthetic pathway to synthesize the following compound. State ALL the reagents used. oodarrow_forwardgive the product of the following reactionarrow_forward
- 1. Devise a synthesis of the tripeptide sequence Phe Thr Lys using acid chloride below and N-methylmorpholine (NMM) for your coupling. Propose a detailed reaction mechanism for this step. You may use any readily available reagents/ protecting groups for your synthesis. In your answer you should clearly state the chosen reagents and how they are introduced and removed in your synthesis. Mechanistic details, for these steps are NOT required. Ph NH2 NH NH NH CO2 но Phe Thr Lys 'NMearrow_forwardOutline a reaction sequencearrow_forwardShow how you would synthesize 1-amino-2-methylbutane from 2-butanone and any other necesary reagentsarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
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