12.4 Grignard Reagents | Organic Chemistry

Chad introduces Grignard reagents in this lesson, one of the more important reagents in organic synthesis as they are used to form a C-C bond. Grignard reagents are one of our more important organometallic reagents, being organomagnesium halides. He describes Grignard reagents explaining why they are strong nucleophiles, how they are made, and how they can be added to aldehydes and ketones to form primary, secondary, or tertiary alcohols (including the grignard addition mechanism). He concludes the lesson with a grignard example showing how to predict possible reactants used in a Grignard reaction to produce a tertiary alcohol.
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00:00 Lesson Introduction
00:43 Introduction to Grignard Reagents and Organometallics
03:30 Grignard Addition to Aldehydes and Ketones
08:12 The Synthesis of Grignard Reagents
09:27 Synthesis of Alcohols with Grignard Reagents (Example)
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because of you. Thank you!

[@ChadsPrep]

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[@ChadsPrep]

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[@princessphemorahsampsonedu101]

This made it easy for me to understand..so helpful😊

[@ChadsPrep]

Excellent - glad to hear it!

[@user-rk2lz2xw8k]

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[@ChadsPrep]

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[@jaydenallegakoen9974]

Amazing video thank you so much

[@ChadsPrep]

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[@ChadsPrep]

You’re welcome, Sura! 😊

[@rohanpatel1864]

Thank you!

[@ChadsPrep]

You're welcome, Rohan!

[@CaseyLada]

This is so helpful, thank you!
Would we be able to use other agents besides H3O+ in the second step as an acid workup? Would H2O work?

[@nikitaliasiuk]

would you consider covering organoboron or organoaluminum grignard reactions and synthesis of them?

[@user-uo3of7yl8i]

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[@ChadsPrep]

You're welcome and Thank You.

[@abdoulazizdabo9064]

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[@ChadsPrep]

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[@ChadsPrep]

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[@gamewarden2813]

ty!

[@ChadsPrep]

You're welcome!

[@ryanalani1262]

Thank you! if there are two groups of aldehyde attached to the same reactant should we use Grignard twice? also what if the reactant were ester or O-CH3-CL or acid chloride?

[@ChadsPrep]

Yes. If you have two aldehyde functional groups on a reactant then the reactant could react with 2 equivalents of the grignard. Esters, acid halides, and acid anhydrides can also react with two equivalents of a grignard too. I cover this in lesson 20.4: czcams.com/video/_1ATaPMZrRQ/video.html
Hope this helps!

[@ryanalani1262]

@@ChadsPrep Thank you so much! I should watch that lesson before the exam yesterday :)
The question was Ester carbonyl group attached to O-Ch3Cl
I am not sure if O-Ch3Cl treated as leaving group or not?

[@user-qs8he1ml3k]

thanks for the video, it's great!
just a quick question, isn't the H3O+ for all 3 of the reactions at 8:00 a type of protic solvent? Or does hydronium not really count as a solvent and something else is supplying it?
Now that I'm checking again, I'm guessing the fact that it's sequential 1. and then 2. means that it can't take H+ from the H3O+ right?

[@ChadsPrep]

Grignard reactions tend to use ether as a solvent. Protic solvents wouold protonate the Grignard and prevent the reaction from happening. For this reason H3O+ is added in the second step of these reaction (i.e. after the Grignard reagent has already reacted)

[@athenapaint]

Thank you! You've helped me get through all of my chemistry classes. Quick question: If the attachments are 2 ethyl groups and a benzine ring, would there still be a 3rd way to synthesize?

[@ChadsPrep]

If any two of the groups were identical there would only be two ways to produce a tertiary alcohol beginning with a ketone. However, you will learn later in the semester that as long as two of the groups are identical you could actually start the synthesis with an ester and add excess grignard. So in this case if you started with a benzene ester (for example methyl benzoate) and then added two equivalents of an ethyl grignard (aka excess) you would get exactly the same product. This will be presented in lesson 20.4. Hope this helps!

[@athenapaint]

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[@ChadsPrep]

Thanks!

[@ramonaparicio6989]

Thank you god

[@ChadsPrep]

Happy Studying!

[@target__iit]

hmm, this may seem like a silly question but what is the difference between a base and a nucleophile

[@ChadsPrep]

Not a silly question! The difference is really down to their action. Both bases and nucleophiles are electron rich species which donate electrons to electron deficient species. The definition of a Lewis base is an electron pair donor, so nucleophiles are Lewis bases which donate a pair of electrons to an electron deficient species, for example a carbon in C=O. The definition of a Bronsted Lowry base is 'accepting' i.e. forming a bond to a proton (H+) so the bases in these reaction pathways are Bronsted Lowry bases. So in organic reaction mechanisms we use the term 'Nucleophile' to describe a Lewis base, i.e. an electron rich species that attacks something other than hydrogen and 'Base' to describe an electron rich species that attacks hydrogen. I hope that is clear :)

[@dylan8951]

ur awesome!

[@ChadsPrep]

Thank you!

[@mahla-nb4ki]

can't LiAlH4 lead to a 3° alcohols?

[@laylams04]

ofc our professor would want the grignard synthesis 🤡