Write the mechanism for the reaction of acetyl chloride with...

Key Concepts

Grignard Reagents

Grignard reagents are organomagnesium halides that function as strong nucleophiles. Their carbon-magnesium bond is highly polarized, allowing the carbon to attack electrophilic centers like carbonyl carbons, making them indispensable tools in forming carbon–carbon bonds in synthetic organic chemistry.

Acid Chlorides Reactivity

Acid chlorides are very reactive acyl compounds due to the electron-withdrawing effect of the chlorine atom, which increases the electrophilicity of the carbonyl carbon. This heightened reactivity makes them prime candidates for nucleophilic acyl substitution reactions.

Nucleophilic Acyl Substitution

This mechanism involves the nucleophilic attack on the carbonyl carbon by the Grignard reagent, forming a tetrahedral intermediate. The intermediate then collapses by expelling the chloride ion, a good leaving group, thus forming a ketone as an intermediate product.

Sequential Nucleophilic Addition

After the formation of the ketone intermediate, a second equivalent of the Grignard reagent adds to the carbonyl group. The resulting alkoxide intermediate, upon treatment with acid during workup, is protonated to produce a tertiary alcohol, showcasing the power of sequential nucleophilic additions in building complex molecules.

Transcript

00:04 Next question is problem 10 write the mechanism for the reaction of acetyl chloride with two equivalents of ethyl magnesium bromant.

00:20 So here we are writing the mechanism of the reaction by that tertiary alcohol is formed and the starting compound is acetyl chloride.

00:33 So, acetyl chloride is ch3 c double bond o in the mechanism you are writing all the electrons then c.

01:03 This is acetyl chloride.

01:07 Now when it is reacting with ethyl magnesium bromide that means c2h5 mgbr.

01:21 So first molecule is here reacting nucleophilic addition is taking place and by that how the addition is taking place here attack of this ethyl group at this carbon atom which is positive and removal of this electron and going to oxygen this is how the tetrahead intermediate compound is formed so that compound is carbon here it will be oxygen with two electrons here one two here and one two here negative charge is also there and magnesium bromide is attest to here because magnesium bromide part is positive and the carbon here already attaches to one methyl group and one chlorine group and one ethyl group is also here.

03:04 C2h5 which is coming from the beginner agent.

03:10 So this is tetrahedral addition compound is formed that is the intermediate compound and in the next step what happens this bond is shifting here double bond is formed and this chlorine is leaving as cl minus so by this the product which is formed is carbon double bond oxygen 1 ch3 group which was already present and 1 c2h5 which is from the grignard reagent.

04:22 So this ketone is formed with the two electrons here...

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