1. (2 pts) Which of the following is in the correct order of reactivity of acid

Question

1. (2 pts) Which of the following is in the correct order of reactivity of acid derivatives towards nucleophilic attack? A) esters> acid anhydrides> amides C) carboxylates esters> amides. E) anhydrides> amides> carboxylates. B) anhydrides> amides> esters. D) anhydrides> acids> acid chlorides. 2. (2 pts) A nitrile can be made by dehydrating an amide. However, for this reaction to occur, the A) primary. B) secondary. C) tertiary. D) N-methylated. E) part of a lactam. 3. (2 pts) Why are p-lactams, such as penicillins and cephalosporins, unusually reactive amides? amide must be

Explanation / Answer

1) E

order of reactivity

acid  chloride > anhydride > ester acid > amide carboxylate

2) A

3) They are unusually reactive because of the ring strain and conformational arrangement , the lone pair of the Nitrogen is not allowed to interact with the double bond of the carbonyl. The oxyanion hole stablizes the tetrahedral intermediate thus reducing the transition state energy

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