acytelene vs ethane acidity..pls help

[toooth]

Advertisement - Members don't see this ad

can somebody please explain to me why Acytelene is more acidic than ethane and what hybirdization have to do with acidity
( sp vs. sp3)?....
thanks...😳

 

[solstice]

Based on Lewis acid definition the acid is a molecule that likes to accept electron, right? There are only two electrons per Pi bond and this orbital experience an electron deficit character most of the time and tehrefore acidic character. The more pi bond the more acidic, so the order of acidity would be thriple bond (Acetylene) Sp> double bond (Ethylene) Sp2> Sigma bond (Ethan)Sp3.

 

[gentile1225]

Agreed! The more s character you have the more acidic a compound becomes. An sp hybridization is 50% s character and 50% p, whereas an sp2 hybridization is 33% s character and 66% p character.

 

[Orgolover]

More S-character involved allows electrons to come closer to nucleus -- this is a form of electron withdrawing, which we know is what makes something acidic, if it draws electrons towards itself. So again, actylene is more acidic cuz it has more S character and therefore is electron withdrawing.