Question

Which is the stronger base, $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{N}$ or $\mathrm{H}_{2} \mathrm{BO}_{3}^{-} ?$

   Which is the stronger base, $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{N}$ or $\mathrm{H}_{2} \mathrm{BO}_{3}^{-} ?$

Chemistry

Paul Flowers, Klaus…

Chapter 14, Problem 39

Instant Answer

Solved by Expert Ronald Prasad

11/09/2020

Step 1

We are given the Kb for $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{N}$, which is $7.4 \times 10^{-5}$. Show more…

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Which is the stronger base, $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{N}$ or $\mathrm{H}_{2} \mathrm{BO}_{3}^{-} ?$

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Key Concepts

Basicity

Basicity refers to the ability of a molecule to accept a proton. It is often assessed by the availability and reactivity of an atom's lone pair electrons, and it can be quantified by the pKa of the conjugate acid. A stronger base has a more available lone pair for bonding and typically forms a more stable conjugate acid.

Lone Pair Availability

The strength of a base is largely determined by how freely available its lone electron pair is for protonation. If the lone pair is delocalized by resonance or is involved with electron-withdrawing groups, its availability decreases, thus reducing the molecule’s basicity.

Inductive and Resonance Effects

Inductive effects involve the donation or withdrawal of electron density through sigma bonds by neighboring substituents. Electron-donating groups increase base strength by pushing electron density toward the active site, while resonance can stabilize or delocalize the lone pair, often reducing basicity. These effects must be considered when comparing different bases.

Molecular Structure Considerations

The overall molecular structure, including the types of atoms present and their bonding environment, plays a critical role in determining a molecule's basicity. Factors such as the electronegativity of the atom bearing the lone pair and the presence of substituents that sterically hinder or electronically modify the basic site are key to understanding differences in base strength.

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