Question

Many moderately large organic molecules containing basic nitrogen atoms are not very soluble in water as neutral molecules, but they are frequently much more soluble as their acid salts. Assuming that pH in the stomach is 2.5, indicate whether each of the following compounds would be present in the stomach as the neutral base or in the protonated form:
(a) nicotine Kb = 7x10^-7
(b) caffeine,Kb= 4x10^-14
(c) strychnine Kb= 1x10^-6
(d) quinine, Kb= 1.1x10^-6

Answer 1

Answer:

a) For nicotine, the protonated form is the present in stomach.

b) For caffeine, the neutral base form is the present in stomach.

c) For Strychinene, the protonated form is the present in stomach.

d) For quinine, the protonated form is the present in stomach.

Explanation:

In a basic dissociation for molecules with basic nitrogen, the equilibrium is:

A + H₂O ⇄ AH⁺ + OH⁻

Where A is neutral base and AH⁺ is protonated form

The basic dissociation constant, kb, is:

$K_{b} = \frac{[AH^+][OH^-]}{[A]}$

As pH in stomach is 2,5:

[OH] =$10^{-[14-pH]}$

[OH] = 3,16x10⁻¹² M

Thus:

$\frac{K_{b}}{3,16x10^{-12}} =\frac{[AH^+]}{[A]}$ (1)

Using (1) it is possible to know if you have the neutral base or the protonated form, thus:

(a) nicotine Kb = 7x10^-7

$\frac{K_{b}}{3,16x10^{-12}} =\frac{[AH^+]}{[A]}$

$\frac{7x10^{-7}}{3,16x10^{-12}} =\frac{[AH^+]}{[A]}$

$221359 = \frac{[AH^+]}{[A]}$

[AH⁺}>>>>[A]

For nicotine, the protonated form is the present in stomach

(b) caffeine,Kb= 4x10^-14

$\frac{K_{b}}{3,16x10^{-12}} =\frac{[AH^+]}{[A]}$

$\frac{4x10^{-14}}{3,16x10^{-12}} =\frac{[AH^+]}{[A]}$

$0,0127 = \frac{[AH^+]}{[A]}$

[AH⁺}<<<<[A]

For caffeine, the neutral base form is the present in stomach

(c) strychnine Kb= 1x10^-6

$\frac{K_{b}}{3,16x10^{-12}} =\frac{[AH^+]}{[A]}$

$\frac{1x10^{-6}}{3,16x10^{-12}} =\frac{[AH^+]}{[A]}$

$314456 = \frac{[AH^+]}{[A]}$

[AH⁺}>>>>[A]

For Strychinene, the protonated form is the present in stomach

(d) quinine, Kb= 1.1x10^-6

$\frac{K_{b}}{3,16x10^{-12}} =\frac{[AH^+]}{[A]}$

$\frac{1,1x10^{-6}}{3,16x10^{-12}} =\frac{[AH^+]}{[A]}$

$347851= \frac{[AH^+]}{[A]}$

[AH⁺}>>>>[A]

For quinine, the protonated form is the present in stomach.

I hope it helps!