Organic Chemistry Simplified: “Breaking Lines” Example (part 3)

Finding Your Nucleophile and Electrophile

Let’s take a quick look at how the last section (Organic Chemistry Simplified Part 2)  can help us figure out how a structure will react. Ultimately, this will show us our nucleophile and electrophile.

Some of you may not have seen this starting material in your class yet; this does not matter. If you apply what we have talked about thus far, you will be able to answer this question. Let me show you…

Start with each functional group separately and figure out the positive and negative charges. As stated before with carbon-carbon double and single bonds, we can place the charges on either carbon atom. Now, let’s take a look at the carbon-oxygen double bond:

We know from before that we always place the negative charge on the more electronegative atom (only one choice). In terms of charges, you never want to have the same charge side by side (on two atoms next to each other). Therefore, there is only one charged structure:

Now, we know this structure must be our electrophile since our nucleophile (Nu-) is written above the arrow in our example. So, our nucleophile has two potential places to attack:

In the next section (Organic Chemistry Simplified Part 4), we will go over how to classify reagents into groups that will make them much more manageable.

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