As written, the following syntheses have flaws. What is wrong with each? (a)(EQUATION CAN'T COPY

As written, the following syntheses have flaws. What is...

Key Concepts

Selectivity (Chemoselectivity/Regioselectivity)

Controlling which specific bonds are formed or broken is key to obtaining the desired product. Poor selectivity can lead to a mixture of products or low yields if side reactions are not properly managed.

Order of Operations in Multi-step Synthesis

The sequence in which reactions are executed is critical for a successful synthesis. An incorrect order can result in the premature reaction or degradation of sensitive functional groups, thereby interrupting the intended synthetic pathway.

Reaction Mechanism Accuracy

A correct understanding of the underlying reaction mechanism is crucial in any synthesis. Errors in mechanism can lead to misidentification of intermediates, improper reagent choice, or steps that are simply nonviable under the conditions provided.

Reagent Compatibility

Ensuring that all reagents and reaction conditions work harmoniously is essential. Incompatible reagents or conditions can cause side reactions, decompose key intermediates, or otherwise lead to inefficient or unsuccessful transformations.

Functional Group Protection and Deprotection

In multi?step syntheses, reactive functional groups may need to be temporarily protected to prevent unwanted reactions. Overlooking a necessary protection or deprotection step can render subsequent reactions ineffective or produce undesired byproducts.

Transcript

00:01 So we're given some schemes here, and we have to determine what the flaws are, what are wrong with each.

00:07 So i think it's important just to go step by step, do each transformation.

00:12 So every time you see a number and then a set of reagents, that's going to give you some isolable product.

00:17 And then you take the next set of reagents under the next number, and you react those.

00:24 So in this case, we're doing chlorination with chlorine and iron chloride.

00:29 So the reagents are fine.

00:30 That's a good combination of taluine.

00:34 And so that we got lucky, that first set there, that's going to give us a mixture of the ortho and para chlorides, even though your product is meta.

00:49 So that's the flaw there, even though the potassium permanganate is going to oxidize that methyl group to a carboxylic acid.

00:59 Your chlorate, you're going to have a mixture of the ortho and para.

01:05 So you can't get the meta that way.

01:09 If you add the carboxylic acid first, it basically, if you flip those steps, you'll be able to get the product.

01:15 So if you do potassium permanganate first and then do the iron chloride, sorry, then do the chlorine with iron chloride.

01:21 You should be able to get the product.

01:23 All right.

01:25 In this step, right, we're going to go step by step, right? i didn't even draw the product.

01:30 I'm sorry.

01:30 I didn't draw the products for either of these.

01:33 Right.

01:34 So we need a chlorine in the one position, a methyl group in the two position, and an amine in the four position.

01:44 Cool.

01:45 So let's do nitration, right? so we're going to do some nitration.

01:51 So that will give us a mixture of ortho and para products.

01:56 Because the nitrogen is probably, they're intending on it being the amino group.

02:01 In the power position.

02:03 I'm not going to write the ortho product.

02:06 So let's assume you can isolate that away.

02:09 So i'll just write the power product.

02:12 Next, we're going to do freocrafts.

02:17 So, yeah, so that would add ortho to the chlorine, meta, to the nitro.

02:26 So that would give us a methyl group here.

02:29 Here's the thing.

02:29 You know so the chemistry is possible right and that's fine that's all fine and dandy but don't be alarmed when i say you can't do that right so you can't use you can't do freud crafts on a ring that is deactivated so adding that nitro group essentially forbids you from doing the freeo crafts to add that final methyl group so that's where the flaw in that step...

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