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Topic: least acidic to most acidic  (Read 8688 times)

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Offline orgostudent

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least acidic to most acidic
« on: April 28, 2008, 05:10:44 PM »
can anyone tell me--which order do these go in (from least to most)

H2O
HBr
NH3
NH2-
(CH3)3COH
CH3C(=O)OH
CH3CH2CH3

Offline macman104

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Re: least acidic to most acidic
« Reply #1 on: April 28, 2008, 08:44:16 PM »
Please give us your attempt.  If you can include your reasoning, it will help in responding to your question, as we can see what things are causing difficulty.  To get started, think about the nature of the bonds (ionic or covalent), resonance, and inductive effects (how do the neighboring atoms stabilize the charge)

Offline peachygirl4444

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Re: least acidic to most acidic
« Reply #2 on: April 29, 2008, 02:26:28 PM »
Pka?

Offline vhpk

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Re: least acidic to most acidic
« Reply #3 on: April 29, 2008, 07:59:19 PM »
can anyone tell me--which order do these go in (from least to most)

H2O
HBr
NH3
NH2-
(CH3)3COH
CH3C(=O)OH
CH3CH2CH3
Yeah, you needn't pKa because you explain this in qualitative way.
First, acidic group: HBr, (CH3)3OH, CH3COOH.
HBr is the most, because of the large size of bromine atom -> polarize the bond H-Br -> H easily separate to form H+. Write the formulae of MeCOOH and t-BuOH, you will see the C=O group is polarized to O -> polarizing O-H group while t-BuOH only has t-Bu group.
Basic group: NH3, NH2-
NH2- is stronger because there is 1 negative charge in its molecule while NH3 doesn't.
H2O is intermediate.
CH3CH2CH3 doesn't have either acidic or basic properties
Genius is a long patience

Offline lutesium

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Re: least acidic to most acidic
« Reply #4 on: April 29, 2008, 09:04:18 PM »
NH2- is a stronger base due to its negative charge which makes it a stronger proton acceptor (basicity charachter).


Lutesium...

Offline lutesium

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Re: least acidic to most acidic
« Reply #5 on: May 04, 2008, 07:17:41 AM »
VHKP I think that you made a mistake while telling the order because the order should be like this:

Acidity in descending order
HBr > CH3COOH > t-BuOH> H2O> NH3 > NH2-
Hydrocarbons have no acidity or basicity charachter.


Lutesium...

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