How is \(\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{2} \mathrm{C}=\mathrm{CH}_{2}\) prepared by a Grignard reaction with \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Br}\) and \(\mathrm{CH}_{3} \mathrm{COOC}_{2} \mathrm{H}_{5}\) as the starting materials?

Short Answer

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Question: Outline the steps to prepare the compound \((\mathrm{C}_{6} \mathrm{H}_{5})_{2}\mathrm{C}=\mathrm{CH}_{2}\) using a Grignard reaction, starting from \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Br}\) and \(\mathrm{CH}_{3}\mathrm{COOC}_{2} \mathrm{H}_{5}\). Answer: The preparation of the compound involves the following steps: 1. Formation of Grignard reagent (\(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{MgBr}\)) by reacting \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Br}\) with magnesium in ether. 2. Reaction of the Grignard reagent with the ester compound (\(\mathrm{CH}_{3}\mathrm{COOC}_{2} \mathrm{H}_{5}\)) to form a ketone (\(\mathrm{C}_{6} \mathrm{H}_{5}\-\mathrm{C}(\mathrm{H})=\mathrm{O}\)). 3. Reaction of the formed ketone with another mole of Grignard reagent, resulting in the alkoxide salt of the target compound. 4. Protonation of the alkoxide salt using an aqueous acid or water, leading to the desired compound \(\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{2}\mathrm{C}=\mathrm{CH}_{2}\) and a magnesium salt side product.

Step by step solution

01

Formation of Grignard reagent

To begin, the Grignard reagent is formed by the reaction between \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Br}\) and magnesium. The magnesium atom inserts itself between the carbon atom and the bromine atom, forming the Grignard reagent \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{MgBr}\). The reaction is as follows: $$\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Br} + \mathrm{Mg} \xrightarrow{\text{ether}} \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{MgBr}$$
02

Reaction of Grignard reagent with the ester compound

Now, the formed Grignard reagent reacts with the ester compound \(\mathrm{CH}_{3}\mathrm{COOC}_{2} \mathrm{H}_{5}\). In the presence of a Grignard reagent, an ester is first converted to a ketone by the nucleophilic attack of the Grignard reagent on the carbonyl carbon and subsequent breakage of the carbon-oxygen double bond: $$\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{MgBr} + \mathrm{CH}_{3} \mathrm{COOC}_{2} \mathrm{H}_{5} \xrightarrow{} \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{MgOOC}_{2} \mathrm{H}_{5} + \mathrm{C}_{6} \mathrm{H}_{5}\-\mathrm{C}(\mathrm{H})=\mathrm{O}$$
03

Reaction of ketone with Grignard reagent

Next, the ketone formed in the previous step reacts with another mole of Grignard reagent. Upon nucleophilic attack by the Grignard reagent, the alkoxide salt of the target compound is formed: $$\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{MgBr} + \mathrm{C}_{6} \mathrm{H}_{5}\-\mathrm{C}(\mathrm{H})=\mathrm{O} \xrightarrow{} \left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{2}\mathrm{C}(O^{\ominus}\mathrm{Mg}^{\oplus}\mathrm{Br})(\mathrm{H})$$
04

Protonation of the alkoxide salt

Finally, the alkoxide salt is protonated using an aqueous acid like dilute \(\mathrm{HCl}\) or water. The magnesium salt formed is a side product and the desired alkene is obtained: $$\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{2}\mathrm{C}(O^{\ominus}\mathrm{Mg}^{\oplus}\mathrm{Br})(\mathrm{H}) + \mathrm{H}_{2}\mathrm{O} \xrightarrow{} \left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{2}\mathrm{C} = \mathrm{CH}_{2} + \mathrm{Mg}(\mathrm{OH})\mathrm{Br}$$ In conclusion, the compound \(\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{2}\mathrm{C}=\mathrm{CH}_{2}\) can be prepared through a series of reactions involving the formation of a Grignard reagent from \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Br}\), reaction with the ester \(\mathrm{CH}_{3}\mathrm{COOC}_{2} \mathrm{H}_{5}\), and subsequent steps leading to the final product.

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