Protic vs. Aprotic

This forum made possible through the generous support of SDN members, donors, and sponsors. Thank you.

Gasedo

Senior Member
10+ Year Member
5+ Year Member
15+ Year Member
Joined
Nov 16, 2005
Messages
192
Reaction score
2
a) CH3OH and b) NH3 are protic.
Why c) HCO2N(CH3)2 is considered aprotic? Protic solvents are polar molecules having a H that can form H-bond. I would say c) is also protic because of the first H in the molecule.
Can anybody explain?
Thanks

Members don't see this ad.
 
In (a) and (b) the Hydrogen is attached to the more electronegative atoms (oxygen and nitrogen respectively)

In (c) the hydrogen is attached to the carbon which is not that electroneg.
 
Gasedo said:
a) CH3OH and b) NH3 are protic.
Why c) HCO2N(CH3)2 is considered aprotic? Protic solvents are polar molecules having a H that can form H-bond. I would say c) is also protic because of the first H in the molecule.
Can anybody explain?
Thanks

Looks like something else is missing in c). It's neither an amide nor an amino acid. Can you look into it and check if the chemical formula has been written correctly?
 
everest said:
Looks like something else is missing in c). It's neither an amide nor an amino acid. Can you look into it and check if the chemical formula has been written correctly?
It is. There is a double bond btw C and O
 
Members don't see this ad :)
Gasedo said:
It is. There is a double bond btw C and O

The double bond need not be shown in a chemical formula unless it's otherwise a structural one.

It will make more sense to me that c) being written as HCON(CH3)2, an amide, instead of HCO2N(CH3)2.
 
everest said:
The double bond need not be shown in a chemical formula unless it's otherwise a structural one.

It will make more sense to me that c) being written as HCON(CH3)2, an amide, instead of HCO2N(CH3)2.
Maybe you are right; I put the 2 there so I could show that is a double bond btw C and O.The double bond is shown in the formula. That's why I was confused too.
If you have Shaum’s organic chem. book you can check it out. It is problem 2.17, page 22
 
Top