Hydrolysis Of Esters And Amides 6

Question 1

What happens when amides undergo hydrolysis?

Answer 1

The amide bond breaks down, which can render the drug inactive, as seen with penicillin antibiotics.

Question 2

Why are cyclic amides in penicillins more reactive?

Answer 2

The 4-membered ring in cyclic amides has strain, making it more susceptible to hydrolysis.

Question 3

How does electron deficiency affect carbonyl reactivity?

Answer 3

The more electron-deficient the carbonyl carbon, the more reactive it is.

Question 4

What is the order of reactivity among common carbonyl groups?

Answer 4

Aldehyde > Ketone > Ester > Amide.

Question 5

Why are esters more reactive than amides?

Answer 5

Esters have two electron-withdrawing oxygen atoms that make the carbonyl carbon more electron-deficient.

Question 6

How does resonance affect the reactivity of esters and amides?

Answer 6

Esters can delocalize electrons through resonance, making the carbonyl carbon less reactive; amides have even more stability due to nitrogen’s ability to delocalize electrons.

Question 7

What makes amides less reactive compared to esters?

Answer 7

The nitrogen’s lone pair can delocalize more effectively than oxygen, increasing the stability of amides

Question 8

How does the stability of amides affect drug activity, as shown in local anesthetics?

Answer 8

Procaine (with an ester) is rapidly hydrolyzed and short-lasting, while lidocaine (with an amide) hydrolyzes more slowly, providing longer-lasting effects.

Question 9

Why is storage advice for drugs like penicillin important?

Answer 9

To prevent hydrolysis of the amide bond, which would make the drug inactive.