1. Ampicillin is an antibiotic used to prevent and treat several bacterial infections. Bacampicillin is a derivative of ampicillin (a prodrug) that enhances the oral bioavailability of the parent antibiotics. In the body, Bacampicillin decomposes to release Ampicillin and side products. Provide a mechanism for the following reaction. For simplicity, replace the core structure with R. NH2 Bacampicillin N NH2 S H3O+ Ampicillin OH Η CO2 Η

I) Sketch a stepwise mechanism for the reaction of secondary amine with an acid chloride to generate an amide and H-CI II) Name the general class of organic compound that each of these molecules belong to i) R NR2 ii) R ii1) iv) R-CEN

Explain why a much better yield of primary amine is obtained from the reaction of an alkyl halide with azide ion (-N3), followed by catalytic hydrogenation. (Hint: An alkyl azide is not nucleophilic.)

The following three derivatives of succinimide are anticonvulsants and have found use in the treatment of epilepsy, particularly petit mal seizures. Ph Ph `N' `N' ČH3 ČH3 Methsuximide Ethosuximide Phensuximide Following is a synthesis of phensuximide. CN Ph CN Ph CN 1. NaOH, H2O 2. HC, Н20 NaOEt KCN Ph-CHO cOOEt H cOOEt NC COOEt 3. Нeat Ethyl cyanoacetate (A) (B) Benzaldehyde Ph Ph Ph CH;NH2 НООС СООН Et0oC COOEt `N' (C) (D) ČH3 Phensuximide Methsuximide is formed by a similar pathway to that shown for phensuximide. Draw the structure of the compound that reacts with ethyl cyanoacetate in the synthesis of methsuximide.

27) Hydrolysis of an ester: O II CH,-C-O-CH2-CH2-CH, + H20 28) Acid/ Base reaction of an amine CH3-CH2-NH2 H2CO3 29) Hydrolysis of an amide 11 CH3-CH2-CH2-CH2-CH2-C-NH-CH2-CH2-CH, + H20 OMIC Molecules

Propose a reagent or reagents to bring about the conversion of F to fluoxetine. Note that the bracketed intermediate formed in this step is an N-substituted carbamic acid. Such compounds are unstable and break down to carbon dioxide and an amine.

The start drug is Tolbutamide and the product is Chlorpropamide. Which of the following is incorrect? a. the -CH3 groyp is replaced with Cl atom to prevent oxidation of –CH3 group   b. The -CH3 group in Tolbutamidw can be easily oxidized into -CH20H, and then to –CO2H   c. this modification is used to prolong the duration of action of chlorpropamide   d. this modification is achieved by an oxygen enzyme   e. none of the above

Give the amine and coupling component of the given compound.

Only typed solution

Compare compounds I and Il and choose which statement below fits best. 'N. vs. column I compound II A Both compounds have the same basicity B) Compound II is MORE basic than the compound I. Compound I is MORE basic than the compound II. D The basicity of the compounds I and II cannot be compared. ZI