Which is a stronger base? ***A brief explanation would be appreciated thanks HS− or HO− CH3O−...

Which is a stronger base? ***A brief explanation would be appreciated thanks

HS− or HO−

CH3O− or CH3NH−

CH3OH or CH3O−

Cl− or Br−

CH3COO− or CF3COO−

CH3CHClCOO− or CH3CHBrCOO−

Expert Solution

A base (an electron rich species) is the one which is capable of donating its lone pair to the approaching acid (an electron deficient species).

OH- is a stronger base than SH-. This is due to the fact that -ve charge is better stabilized in S as it has vacant orbitals and thus is less prone to donate the electron pair to H+ or acind no such stabilization exist in case of O and thus electron pair is available for donation and acts as a stronger base.

CH3NH- is a stronger base than CH3O-. N is less electronegative and thus its electron pair is loosely held as compared to the more electronegative O atom.

CH3O- is a better base than CH3OH. Infact alcohols are almost neutral or mildly acidic. CH3O- on the other hand has electron pair available for donation.

Cl- is a stronger base than Br-. Its conjugate acid HBr is a stronger acid than HCl. The explanation is similar to the one for SH- and OH-.

CH3COO- is a stronger base than CF3COO- which has three electronegative F attached to alpha carbon next to COO-. F is electron withdraqing in nature and would pull electrons towards itself, making the species less basic.

CH3CHBrCOO- is a better base than CH3CHClCOO-. Cl is more electronegative than Br- and would show a strong electron withdrawing effect on the COO- electron pair, thus making it less basic.

queen_honey_blossom answered 2 years ago

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