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- When 4-dimethylaminopyridine (DMAP) is added in catalytic amounts to acetic anhydride and an alcohol, it significantly increases the rate of ester formation. The process begins with a reaction between acetic anhydride and DMAP to form a highly reactive acetylpyridinium intermediate that is more reactive than acetic anhydride itself. Propose a mechanism for this process that includes the formation and reaction of the acetylpyridinium intermediate.In the presence of a trace of acid, d@hydroxyvaleric acid forms a cyclic ester (lactone).HO¬CH2CH2CH2CH2¬COOHd@hydroxyvaleric acid(a) Give the structure of the lactone, called d@valerolactone.(b) Propose a mechanism for the formation of d@valerolactone.The first step in the citric acid cycle of food metabolism is reaction of oxaloacetate with acetyl CoA to give citrate. Propose a mechanism, using acid or base catalysis as needed.
- In the Ritter reaction, an alkene reacts with a nitrile in the presence of strong aqueous sulfuric acid to yield an amide. Propose a mechanism.One step in the urea cycle for ridding the body of ammonia is the conversion of argininosuccinate to the amino acid arginine plus fumarate. Propose a mechanism for the reaction, and show the structure of arginine.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.
- 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?In dilute aqueous base, (R)-glyceraldehyde is converted into an equilibrium mixture of (R,S)-glyceraldehyde and dihydroxyacetone. Propose a mechanism for this isomerization.Treatment of a cyclic ketone with diazomethane is a method for accomplishing a ring-expansion reaction. For example, treatment of cyclohexanone with diazomethane yields cycloheptanone. Propose a mechanism.
- 3-Amino-2-oxindole catalyzes the decarboxylation of a-keto acids.a. Propose a mechanism for the catalyzed reaction.b. Would 3-aminoindole be equally effective as a catalyst?Treatment of benzene with sucdnic anhydride in the presence ofpolyphosphoric acid gives the foftlowing γ-ketoacid. Propose a mechanism for this reaction.Propose a mechanism for the reaction of methyl isocyanate with 1-naphthol to giveSevin® insecticide.