Problem: Pyridine and methanol can act as weak bases. Their Kb values are given below. Consider the compounds water, ethylamine, acetone, and aniline, whose Kb values can be found here. Classify them by whether they can be appreciably (Keq> 1) protonated by: pyridinium, CH3OH2+, both, or neither. A higher Kb means a stronger base, and a stronger base is more likely to accept a proton (i. e. , become protonated). A compound can be protonated by pyridinium if it is a stronger base than pyridine. A compound can be protonated by CH3OH2+ if it is a stronger base than methanol.

🤓 Based on our data, we think this question is relevant for Professor Kreis' class at SFU.

FREE Expert Solution

For this problem, the smaller the Kb the more unlikely the base to accept a proton

Analyzing each molecule:

a. ethylamine: 

6.3x10-4 > 1.5x10-9 (pyridinium)

6.3x10-4 > 6.3x10-17 (methanol+)

Hence, ethylamine can be protonated by pyridinium and methanol+

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Problem Details

Pyridine and methanol can act as weak bases. Their Kb values are given below. 

Consider the compounds water, ethylamine, acetone, and aniline, whose Kb values can be found here. Classify them by whether they can be appreciably (Keq> 1) protonated by: pyridinium, CH3OH2+, both, or neither. 

A higher Kb means a stronger base, and a stronger base is more likely to accept a proton (i. e. , become protonated). 

A compound can be protonated by pyridinium if it is a stronger base than pyridine. A compound can be protonated by CH3OH2+ if it is a stronger base than methanol.

Frequently Asked Questions

What scientific concept do you need to know in order to solve this problem?

Our tutors have indicated that to solve this problem you will need to apply the Acid Base Equilibrium concept. You can view video lessons to learn Acid Base Equilibrium. Or if you need more Acid Base Equilibrium practice, you can also practice Acid Base Equilibrium practice problems.

What professor is this problem relevant for?

Based on our data, we think this problem is relevant for Professor Kreis' class at SFU.