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End product of the following sequence of...

End product of the following sequence of reactions is
`CH-=CH overset(CH_(3)MgBr)to overset(HgSO_(4)//H_(2)SO_(4))to underset(Delta)overset(Ag_(2)O)to`

A

`CH_(3)-underset(H)underset(|)overset(OH)overset("||")C-COOH`

B

`CH_(2)(COOH)_(2)`

C

`OHC-CH_(2)-COOH`

D

`H-overset(O)overset("||")C-CH_(2)COOH`

Text Solution

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The correct Answer is:
To determine the end product of the given sequence of reactions, we will go through each step systematically. ### Step 1: Reaction of Acetylene with Grignard Reagent The starting compound is acetylene (CH≡CH). When acetylene reacts with the Grignard reagent (CH₃MgBr), the nucleophilic carbon from the Grignard reagent attacks one of the carbon atoms of the acetylene, leading to the formation of a new carbon-carbon bond. **Reaction:** \[ \text{CH} \equiv \text{CH} + \text{CH}_3\text{MgBr} \rightarrow \text{CH} \equiv \text{C} - \text{C}(\text{CH}_3) - \text{MgBr} \] This results in the formation of a magnesium alkynyl compound (propyne) and methane (CH₄) as a byproduct. ### Step 2: Reaction with Carbon Dioxide Next, the magnesium alkynyl compound reacts with carbon dioxide (CO₂) in the presence of an acid (H⁺ or H₃O⁺). The negatively charged carbon from the alkynyl compound attacks the carbon of CO₂, forming a carboxylic acid. **Reaction:** \[ \text{CH} \equiv \text{C} - \text{C}(\text{CH}_3) - \text{MgBr} + \text{CO}_2 \rightarrow \text{CH} \equiv \text{C} - \text{C}(\text{CH}_3) - \text{COOH} \] This results in the formation of a carboxylic acid (2-methylpropenoic acid). ### Step 3: Hydration with HgSO₄ and H₂SO₄ The next step involves the hydration of the alkyne using mercuric sulfate (HgSO₄) and sulfuric acid (H₂SO₄). This reaction leads to the formation of an enol, which can undergo keto-enol tautomerism. **Reaction:** \[ \text{CH} \equiv \text{C} - \text{C}(\text{CH}_3) - \text{COOH} \xrightarrow{\text{HgSO}_4, \text{H}_2\text{SO}_4} \text{CH}_3\text{C}(OH)=\text{C}(\text{COOH}) \] This results in the formation of an enol which can tautomerize to form a ketone. ### Step 4: Tautomerization The enol formed can tautomerize to a ketone, leading to the formation of a more stable structure. **Tautomerization:** \[ \text{CH}_3\text{C}(OH)=\text{C}(\text{COOH}) \rightleftharpoons \text{CH}_3\text{C}=\text{C}(\text{COOH}) \] ### Step 5: Oxidation with Ag₂O Finally, the ketone undergoes oxidation with silver oxide (Ag₂O), which is a mild oxidizing agent. This oxidation converts the aldehyde group to a carboxylic acid. **Reaction:** \[ \text{CH}_3\text{C}=\text{C}(\text{COOH}) + \text{Ag}_2\text{O} \rightarrow \text{CH}_2(\text{COOH})_2 \] This results in the formation of malic acid (CH₂(COOH)₂). ### Final Product The end product of the sequence of reactions is malic acid, represented as: \[ \text{CH}_2(\text{COOH})_2 \]

To determine the end product of the given sequence of reactions, we will go through each step systematically. ### Step 1: Reaction of Acetylene with Grignard Reagent The starting compound is acetylene (CH≡CH). When acetylene reacts with the Grignard reagent (CH₃MgBr), the nucleophilic carbon from the Grignard reagent attacks one of the carbon atoms of the acetylene, leading to the formation of a new carbon-carbon bond. **Reaction:** \[ \text{CH} \equiv \text{CH} + \text{CH}_3\text{MgBr} \rightarrow \text{CH} \equiv \text{C} - \text{C}(\text{CH}_3) - \text{MgBr} \] ...
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