00:02
This is the answer to chapter 22, problem number 10 from the smith organic chemistry textbook.
00:10
And this problem is asking us to rank a two series of three molecules each based on their reactivities.
00:20
And since this is the carboxylic acid derivatives chapter, of course, each of these molecules is a carboxylic acid or carboxylic acid derivative.
00:30
And so in order to put these in a ranking from least reactive to most reactive, what we have to do is look at what we call the z group.
00:45
And so i've drawn over here on the right side of the screen in blue, sort of a template for a carboxylic acid or carboxylic acid derivative.
00:56
And z is the part of the molecule that we're always going to consider when we're talking about the reactivity of these molecules.
01:06
And so above that in green, i've written some of the rules.
01:10
So the weakest base is going to be the best leaving group.
01:14
A better leaving group is going to make the molecule more reactive, and therefore the weaker the base is the more reactive the molecule is.
01:23
And so when we apply this to a, we see that nh2 is going to be deprotonated ammonia, and so that's an extremely powerful base.
01:36
And so going by these rules, since a weak base is more reactive, a very strong base like deprotonated ammonia is going to be not very reactive.
01:48
Then in the middle we'll have methoxide, o -c -h -3.
01:55
It's a strong base, but not as strong as deep protonated ammonia is going to be.
02:00
And then the most reactive is going to be the acyl chloride, because remember the chloride ion is not a very strong base at all.
02:10
It's the conjugate base of a very strong acid, and therefore it's a very weak base...