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- The Darzens reaction invoIves a two-step, base-catalyzed condensation of ethyl chloroacetate with a ketone to yield an epoxy ester. The first step is a carbonyl condensation reaction, and the second step is an SN2 reaction. Write both steps, and show their mechanisms.The following reaction involves a hydrolysis followed by an intramolecular nucleophilic acyl substitution reaction. Write both steps, and show their mechanisms.When ethyl benzoate is heated in methanol containing a small amount of HCl, methyl benzoate is formed. Propose a mechanism for the reaction.
- Draw structures corresponding to the following names: (a) Phenyl benzoate (b) N-Ethyl-N-methylbutanamide (c) 2,4-Dimethylpentanoyl chloride (d) Methyl 1-methylcyclohexanecarboxylate (e) Ethyl 3-oxopentanoate (f) Methyl p-bromobenzenethioate (g) Formic propanoic anhydride (h) cis-2-Methylcyclopentanecarbonyl bromideIn the mixed Claisen reaction of cyclopentanone with ethyl formate, a much higher yield of the desired product is obtained by first mixing the two carbonyl components and then adding base, rather than by first mixing base with cyclopentanone and then adding ethyl formate. Explain.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.
- Treatment of 2-cyclohexenone with HCN/KCN yields a saturated keto nitrile rather than an unsaturated cyanohydrin. Show the structure of the product, and propose a mechanism for the reaction.Show the products from reaction of p-bromoaniline with the following reagents: (a) CH3I (excess) (b) HCl (c) HNO2, H2SO4 (d) CH3COCl (e) CH3MgBr (f) CH3CH2Cl, AlCl3 (g) Product of (c) with CuCl, HCl (h) Product of (d) with CH3CH2Cl, AlCl3