Rank the compounds in each set in order of increasing acid streng...

Question

Rank the compounds in each set in order of increasing acid strength.
(a) CH3CH2COOH, CH3CHBrCOOH, CH3CBr2COOH

Accepted Answer

All right. Hi everyone. So for this question, you must rank these compounds from the least acidic to the most acidic. But before we discuss these compounds individually. Let's recall that the acidity of a given molecule is discussed by what we refer to as the aerial concept. Right, so Ariel is going to stand for adam residents inductive effect and finally orbital. Right? So to go through each of these individually, adam refers to the fact that protons bonded to electro negative atoms directly tend to be more acidic resonance refers to the fact that if a conjugate base of an acid is stabilized via resonance, then that acid is going to be more acidic inductive effect refers to the fact that the presence of electro negative atoms on an acid increase their acidity. And lastly, um the greater the s character of an orbital, the greater acidity you are going to see. So as p orbital are the most acidic and sp three orbital are the least acidic. So with that being said, if we go ahead and look at each of these three crab oxalic acids that were given in the question individually will notice that they only differ in the identity of the electro negative atom that they have. Right? So we have flooring, bromine and chlorine respectively. And each asset has the same amount of carbons. Each has two carbons and the electro negative atom in question is the same distance away from the carb oxalic acid. So if an electro negative atom is bonded to our carb oxalic acid, then that means we're going to be discussing the inductive effect with respect to each of these crab oxalic acids. So recall that there are a few factors that um that affect the inductive effect of a carb oxalic acid, the first of which is going to be the electro negativity of the atom itself, meaning that if your atom is more electro negative, you're going to see a greater acidity or a higher acidity. The second factor is simply the number of electro negative atoms in your molecule. So if you have more electro negative atoms, you're gonna see higher acidity. And lastly your third factor is going to be your distance between the electro negative atom and the crab oxalic acid group itself. So if your electro negative atom is closer to your car oxalic acid group, acidity is going to increase. So like we mentioned before, um like you mentioned before, we have the same amount of electro negative atoms for each crop oxalic acid and they are the same distance away from the crowd oxalic acid group itself. So that means that the electro negativity of each individual atom is going to determine our acidity in this case. So recall really quickly that um in the periodic table, your electro negativity is going to decrease as you go down the group. Right? So florian is gonna be up top followed by chlorine followed by bruni. Right? So your electro negativity is going to decrease as you go down, which means that flooring is the most electro negative and um bruning is going to be the least electro negative. So if I go ahead and make a list of top from least to most acidic because our floral crop oxalic acid has the most electro negative atom, it is going to be the most acidic and therefore right if borrowing is the least electro negative of these atoms um in the question then the bromo carb oxalic acid is going to be the least acidic and that leaves us with chlorine in between. Right? So I'm not sure I'm gonna have enough space for chlorine for the chloral products of the acid actually. So let me go ahead and move some of these around. There we go. So like I mentioned before, chlorine is gonna be in between. Like so and this is going to be your final answer. This is going to be your final answer. Because fleury given that it's the most electro negative, is going to make that carb oxalic acid the most acidic and bro means going to make the least acidic because it's the least electro negative of the three atoms that we're comparing. So with that being said um thank you very much for watching and I hope you found this helpful

My Courses

Chemistry

Biology

Math

Physics

Business

Social Sciences

Programming

Product & Marketing

Rank the compounds in each set in order of increasing acid strength. (a) CH3CH2COOH, CH3CHBrCOOH, CH3CBr2COOH