Draw the product formed when CH3CH2CH2MgBr is treated with each compound.

Name: Problem 40, Chapter 20: Organic Chemistry
Uploaded: 2019-06-01T21:08:35-08:00
Duration: 5 min 50 s
Channel: Colton K
Description: Draw the product formed when CH3CH2CH2MgBr is treated with each compound.

step 1 Okay, another long problem. This time we're going to react this profile grineered with a variety

Draw the product formed when CH3CH2CH2MgBr is treated with...

Key Concepts

Reaction Workup and Protonation

Following the initial nucleophilic attack of a Grignard reagent on an electrophile, a subsequent reaction step—usually an acid or water workup—is required to protonate the intermediate species. This step neutralizes the anionic intermediate (such as an alkoxide) and yields the final, stable organic product, such as an alcohol or other functionalized compound.

Carbon–Carbon Bond Formation

One of the most important features of reactions involving Grignard reagents is the formation of carbon–carbon bonds. This process is fundamental in synthetic organic chemistry, as it allows the construction of larger and more intricate carbon frameworks, which is key for building complex molecules from simpler precursors.

Grignard Reagents

Grignard reagents are organometallic compounds typically generated by reacting an alkyl or aryl halide with magnesium in an anhydrous ether solvent. They possess a carbon?magnesium bond, where the carbon exhibits significant nucleophilic character. This allows them to act as strong bases and nucleophiles, initiating a variety of transformations by attacking electrophilic centers in other molecules.

Nucleophilic Addition Reactions

A central aspect of Grignard reagent chemistry is nucleophilic addition, where the electron?rich carbon in the reagent attacks an electrophilic carbon, typically one with a partial positive charge, such as the carbonyl carbon in aldehydes or ketones. This addition creates a new carbon–carbon bond, setting the stage for forming more complex organic molecules after subsequent transformations.

Transcript

00:01 Okay, another long problem.

00:03 This time we're going to react this profile grineered with a variety of electrophiles.

00:16 First, if we react it with formaldehyde and water, of course this greener is going to attack directly to open it up, but there's no leaving group so it can only add once.

00:35 This now we'll have our alcohol.

00:40 Here are two hydrogens of the original formaldehyde for b, we have this ketone followed by water.

00:56 So of course, it's the grineered attacks.

00:59 We're just going to add to the carbineal directly.

01:05 To get to this product.

01:08 For c, we now have this acyl chloride.

01:19 And of course, your grignard can actually attack twice, once to kick off the chloride, and then the second time to attack the ketone.

01:29 So now we're going to have this alcohol.

01:31 With two of these propyl groups attached.

01:41 For d, we actually have, seems to be an ester.

01:54 And so again, we have a good leaving group.

01:57 So we're going to add our greenerate twice.