When talking about acidity and basicity of alcohols, does the equilibrium shift towards the stronger acid? (No. It is shifted from a stronger acid to a weaker acid. - GS).

How do we determine basicity between different amines? (Conjugation of the electron pair on nitrogen reduces basicity of the amine. - GS).

Could you please explain how to tell the strength of an acid from looking at its structure? (For neutral acids, remove H+ and evaluate stability of the remaining anion (= conjugate base), taking into consideration electronegativity of atoms holding the negative charge, and number of resonance structures. - GS).

Would the acid base formula usually go Base + Acid → X? (It is typical for Lewis acids and bases - GS). And it would always go Base + Acid ←→ Acid + Base? (It is typical for Bronsted acids and bases. - GS).

Most of an acid is ionized when pH is larger than pKa, so would practically none of the acid be ionized if the pka was larger than the pH? And then about half would be ionized when the pH and the pKa are roughly equal? (Correct. - GS).

Would be correct to affirm that a ph-7.4 is half ionized? (Yes for acids with pKa = 7.4 - GS) To be half-ionized shouldnt be a ph=7? (Yes for acids with pKa = 7 - GS).

Would NH3+ be the conjugate base to H3O+ (the acid) in this example because H3O+ donates a H+ to produce NH3+? (No. H2O is the conjugate base to H3O+, because when H3O+, loses H+, it becomes H2O. The other pair is NH3 / NH4+ - GS).

I thought amines were classified as basic? (They can be both basic because of the lone electron pair, and acidic because of the N-H bond. It is called “amphoteric. - GS).

How do you know whether something is in the ortho- or para- position’s affecting its pKa? (If that something stabilizes either conjugate acid or base by being involved into their resonance structures, - GS).

So when the pH equals the pKa, in this case when the pH=9, then the amino groups would only be half protonated, correct? (Almost. Half of them will be fully protonated. - GS)

Is the hydrogen on the alpha carbon more acidic than the hydrogen on the OH group of the carboxylic acid?  (Their pKas are about 17 and 5 correspondingly. - GS.) What about if there are two carbonyl groups attached by an alpha carbon? (That pKa is about 9 - GS).

Acid donates H+, does conjugative acid accept H+? (No. Bronsted bases accept H+ - GS).

What was it you said in lecture about if the pKa>pH then that means. .  . ? I know on the blog you said pKa = pH, the concentrations of acid and conjugate base are equal, but does that mean that if the pKa>pH the concentration of the conjugate base is greater than the concentration of acid?  (No. Equilibrium favors the acid under those conditions. - GS).

I’m still having a little trouble in relating pKa to pH in terms of deprotonation. (If pKa = pH, the concentrations of acid and conjugate base are equal. - GS)

Just making sure: when a carboxylic acid and an amine react without heat and without a catalyst the product is an ammonium salt but when a carboxylic acid and an amine react with either heat or with a catalyst the product is an amide? (You are correct. - GS).

(Here are 6 common pitfalls for chemical structure, bonding, and acids-bases: https://drive.google.com/file/d/0BxwgAv6oGg81aXM0WmxoYVU1WVk/view?usp=sharing   - GS).

When the pKa of a particular compounds is lower, does that mean it protonates more as opposed to if it were higher? (No, it is a stronger acid and tries to get rid of protons. - GS). Would it deprotonate at such higher pKas? (No - GS). Why is this?(Because at higher pH (it is a weaker acid and holds protons tighter. - GS).

How can a reactant mixture be made basic without adding a hydroxide salt? I know that if a salt contains an anion that reacts with water to produce hydroxide ions and also contains a cation that does not react with water then the resulting solution would be expected to be basic ... (Yes, this is one way. Another one is formation of hydroxide-anions in a redox-reaction. - GS).

A compound is more acidic when the bond between two molecules is weaker? (No. It is more acidic when the conjugate base is more stable and the acid is less stable. - GS).  Is a primary compound  less acidic than secondary and a secondary compound  less acidic than tertiary? (No. It depends on a specific acid-base pair. - GS). So basically if its attached with a triple bond its more acidic than if it were attached with a double bond and so on? (If you mean hydrogen attached to a carbon connected with a multiple bond - yes. - GS).