Ether and COOH question

[kungfupanda2]

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1. Why are ethers so inert?
I have no idea why a C-O single bond is so unreactive when a C=O double bond is much more reactive and electrophilic.

2. Which hydrogen is more acidic in a carboxylic acid--the alpha hydrogen or the hydroxyl hydrogen?
I can only assume it is the hydroxyl hydrogen. I think if the alpha hydrogen were abstracted, one of the resonance structures would probably show a positive charge on the hydroxyl hydrogen (which means the conjugate base would be unstable and less likely to form), but I am not sure since I am terrible at drawing resonance structures!

 

[pfaction]

1) Carbonyl carbon is slightly positive due to the =O pulling in electrons. It's susceptible to nucleophilic attack, see entire carbonyl reactions.

Ethers are weak bases: O can pull off a proton.

R-O-R + 2 H-X => 2 R-X + H2O

See if you can work out the mechanism!

2) Due to resonance, the -OH.
CH3COOH
That H on the OH is going to fly off so the oxygens can distribute a negative charge.

Note that in carbonyls and other reactions like E2, as in the aldol condensation reaction this is not really he case.