[retretretretretret]

I'm studying for a test and I have many questions. Any help with any number of them is greatly appreciated.

1. Would CH3CH2OH (Lewis base) + HCl form CH3CH2OH2+ and Cl- or CH3CH2OH-HCL?
2. Would B(CH3)3 (Lewis acid) + OH- form (CH3)2B-O and CH4?
3. Would protonized Imidazole (C3H3N2H2+(?)) have more than 3 resonance forms?
4. Why would CH3F have a smaller dipole moment than CH3Cl if Fluorine is more electronegative?
5. Is the O-H hydrogen in ethanoic acid (CH3COOH) more acidic than the C-H hydrogen because of the resonance between the 2 O atoms? Is there even any resonance there? I'm asked to explain why using resonance forms.
6. Is tert-butoxide anion a strong enough base to react with water? Its pKa is 18. I don't really see why not, so I don't know what concept I'm even supposed to be working on here. Water has a pKa of 15 or something.

[retretretretretret]

K so since I didn't get any replies I had to find the answers myself and in case someone needs these answers too...

1. CH3CH2OH+ and Cl- (generally you would need both a lewis base and lewis acid reacting to get an acid-base complex, but here we have a bronsted-lowry acid)
2. Yes (aaaactually still not totally sure about that, but I think it's right)
3. Nope, just 3
4. The C-F bond is shorter than the C-Cl bond and dipole moments are proportionate to r (u=Qxr), so the smaller radius in CH3F makes for a smaller dipole moment.
5. Yyyyyes... tentatively. I'm thinking the resonance would decrease the electron density around the O-H oxygen atom so that bond is weaker and the O-H hydrogen is more easily released than the C-H hydrogen.
6. No it's not, because it's the conjugate base in this reaction is stronger than the ter-butoxide.

[ooosh]

Seems you still don't know how to compare acidity or alkalinity by pKa.

[SVXX]

Note : In all acid-base reactions, the end products are always the weaker base and weaker acid. This is due to equilibrium considerations.

1. Ethyl alcohol would first get protonated by HCl as it is a strong acid and -OH is an acid-labile group. Thus the protonated intermediate and Cl^- would form, which would lead to a nucleophilic substitution giving ethyl chloride as end product, but that's a different story.

2. I see no reason why the methyl group would leave like that...not sure about this one. Possibly so.

3. Imidazole is amphoteric..the protonation would occur at the nitrogen which is at 3-position, or the nitrogen having a double bond. Doesn't look like it will have more than 3 resonance forms.

4. Dipole moment is a vector, being the product of charge(scalar) and distance(vector). The size of fluorine is very small, decreasing the distance factor considerably. But the size of chlorine is large compared to fluorine, so even though the negative charge on fluorine would be strong, methyl chloride has the larger dipole moment. This is the easiest way I could think of to explain it to you. I don't remember the actual reasons.

5. Check the stability of the conjugate base that would form, by removing protons from the required locations. If we remove a proton from O, resonance occurs freely between the two O atoms. This delocalises the negative charge, in turn stabilizing the conjugate base. However if we remove a proton from the methyl group, there is no scope for resonance and the base is not stable in any way (though COOH provides a -I effect in the second case, resonance in the first case is a stronger stabilizer). Thus the proton attached to O is more acidic.

6. Water is amphoteric...it would readily react in an acid base reaction as tert-butoxide anion is not stabilized by any factor.

Disclaimer : I do not guarantee that my answers are in any way correct.