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The ammonium ion ( NH4+, pKa=9.25) has a lower pKa than the

methylammoniumion (CH3NH3+ , pKa=10.66). Which is the stronger

base, ammonia NH3or methylamine CH3NH2 ? Explain.

Short Answer

Expert verified

MethylamineCH3NH2 is a stronger base than ammoniaNH3 . Therefore the conjugate base of the methylammonium ion is stronger. Therefore, methylamine is a stronger base than ammonia.

Step by step solution

01

Acid-Base Strength

Acids differ in their ability to donate H+. Stronger acids, such as HCl, react almost completely with water, whereas weaker acids, such as acetic acid (CH3COOH), react only slightly. The exact strength of a given acid HA in water solution is described using the acidity constant (Ka) for the acid-dissociation equilibrium.

HA+H2O⇄A−+H3O−Ka=[H3O+][A−]HA

02

Identify the stronger base with the help of  value

Acid strengths are normally using pKavalues rather thanKa values, where the pKais the negative common logarithm ofKa:

pKa=-logKa

The stronger base has a larger pKa, and the weaker base has a smaller pKavalue.

03

Predict the stronger base between ammonia  & methylamine  

The stronger the acid (smaller ), the weaker its conjugate base. Since is a stronger acid than , methylamine is a stronger base than ammonia.

Note: Since methylamine has an electron-donating group (methyl). Therefore electron density on nitrogen atom increase. Hence it is a stronger base, whereas, in ammonia, an electron-donating group is absent. So it is a weak base when compared to methyl amine.

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