The compound MON-0585 is a nontoxic, biodegradable larvicide that is highly selective against mo

step 1 All right. This is a pretty neat synthesis problem. We have to make this compound Mon 0585, star

The compound MON-0585 is a nontoxic, biodegradable larvicide...

Key Concepts

Retrosynthetic Analysis

Retrosynthetic analysis is a strategic tool used in organic synthesis to break down a target molecule into simpler precursor structures. By working backward from the desired complex structure, chemists can identify readily available starting materials and devise a series of transformations required to construct the molecule. This method is particularly valuable when designing syntheses that start with simple aromatic compounds.

Functional Group Interconversions

This concept refers to the process of transforming one functional group into another to achieve the desired molecular architecture. In the context of synthesizing complex aromatic compounds, controlled interconversion reactions are used to introduce or modify functional groups, thereby enabling further elaboration of the aromatic core. Mastery of these transformations is key in efficiently constructing the target molecule from basic aromatic building blocks.

Aromatic Chemistry

This concept involves the study and utilization of reactions that form or modify aromatic compounds. In synthesis, benzene and phenol are fundamental starting materials whose stability and reactivity under electrophilic conditions enable the formation of diverse substituted aromatic structures. Understanding aromatic chemistry is essential for designing pathways that build complex molecules from simple aromatic rings.

Electrophilic Aromatic Substitution (EAS)

EAS is a vital reaction mechanism in aromatic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. It is commonly used to introduce various substituents onto benzene or phenol, thereby enabling the stepwise construction of more complex molecular frameworks. The direction and rate of substitution are influenced by existing substituents on the ring, making an understanding of EAS critical for planning selective syntheses.

Transcript

00:01 All right.

00:02 This is a pretty neat synthesis problem.

00:04 We have to make this compound mon 0585, starting from either benzene or phenol.

00:12 Well, we don't have to start.

00:13 We can start from either, and then we can incorporate the other if we need to.

00:16 It just says those need to be the only sources of our aromatic rings.

00:20 So there are definitely a few ways to do this.

00:24 I thought, the way that i thought of first was to find a way to simply.

00:31 Synthesize each of the substituents on each of the rings and then combine the two rings in the last step.

00:38 So you know that we can start from phenol.

00:41 So there is an oh group here.

00:44 So i started with phenol because that was the more obvious place to start being that there was a fnol in our product.

00:52 And i recognize that all of the positions, all of the substituents with relation to that phenol are ortho, or para to it.

01:03 So i recognized that oh is an ortho -paradirector.

01:08 It's also a strong activator, so it's going to prefer the addition of those groups in those positions.

01:15 So i had first done a friedelcraft's alkylation with two equivalents of the tertbutyl chloride.

01:24 Not the most efficient way to do it, but i don't think we have much of a choice here.

01:28 You know that you're probably going to get some orthopara product as opposed to the diortho product.

01:35 But with these textual problems, we can thank ourselves that we could thank ourselves that we're not in the lab actually doing this so you can isolate away any of the bi -products.

01:47 So i was able to make that fragment, and that would free up this paraposition activated by the hydroxyl group, which is a more strong director.

01:58 It's a stronger director than either of the turpudal groups.

02:01 So it's going to override their ortho -powering abilities.

02:07 So the next thing we're going to add is going to be at that power position...

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