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Complete the following reaction sequence...

Complete the following reaction sequence :
`CH_(3)-overset(O)overset(||)C-CH_(3)overset((i)CH_(3)MgBr)underset((ii)H_(2)O)rarr(A)overset("Na metal")underset("ether")rarr(B)overset(CH_(3)-Br)rarr(C)`

A

Identical

B

positional isomers

C

functional isomers

D

optical isomers

Text Solution

AI Generated Solution

The correct Answer is:
To complete the reaction sequence provided in the question, we will analyze each step carefully and identify the products A, B, and C. ### Step 1: Reaction of Propanone with Grignard Reagent The starting compound is propanone (CH₃C(=O)CH₃). When it reacts with the Grignard reagent (CH₃MgBr), the nucleophilic carbon of the Grignard reagent attacks the electrophilic carbon of the carbonyl group (C=O). **Reaction:** 1. **Nucleophilic attack:** The CH₃ group from CH₃MgBr attacks the carbonyl carbon, leading to the formation of a tetrahedral intermediate. 2. **Formation of Alkoxide:** The oxygen of the carbonyl group becomes negatively charged (alkoxide), and the magnesium bromide ion (MgBr) associates with it. **Product A:** The product after the first step is an alkoxide: \[ \text{CH}_3C(OH)(CH_3)MgBr \] This compound is 2-methylpropan-2-ol (also known as tert-butanol) after hydrolysis with water. ### Step 2: Reaction with Water Next, we add water (H₂O) to the reaction mixture, which protonates the alkoxide oxygen, leading to the formation of the alcohol. **Reaction:** 1. **Protonation:** The alkoxide oxygen (O⁻) attracts a proton (H⁺) from water, resulting in the formation of the alcohol and the release of MgBrOH. **Product A (Final):** The final product after this step is: \[ \text{CH}_3C(OH)(CH_3) \] This is 2-methylpropan-2-ol. ### Step 3: Reaction with Sodium Metal The next step involves the reaction of product A with sodium metal in ether. Sodium metal reduces the alcohol to form a sodium alkoxide. **Reaction:** 1. **Reduction:** Sodium donates an electron to the alcohol, leading to the formation of a sodium alkoxide. 2. **Formation of Product B:** The hydrogen from the hydroxyl group is replaced by sodium. **Product B:** The product formed is: \[ \text{CH}_3C(O^{-}Na)(CH_3) \] This is sodium 2-methylpropan-2-olate. ### Step 4: Reaction with Methyl Bromide Finally, product B reacts with methyl bromide (CH₃Br). The sodium alkoxide acts as a nucleophile and attacks the electrophilic carbon in methyl bromide. **Reaction:** 1. **Nucleophilic substitution:** The sodium ion (Na⁺) is replaced by the methyl group from methyl bromide. 2. **Formation of Product C:** The product formed is an ether. **Product C:** The final product is: \[ \text{CH}_3C(OCH_3)(CH_3) \] This compound is 2-methoxy-2-methylpropane. ### Summary of Products: - **Product A:** 2-methylpropan-2-ol - **Product B:** Sodium 2-methylpropan-2-olate - **Product C:** 2-methoxy-2-methylpropane ---

To complete the reaction sequence provided in the question, we will analyze each step carefully and identify the products A, B, and C. ### Step 1: Reaction of Propanone with Grignard Reagent The starting compound is propanone (CH₃C(=O)CH₃). When it reacts with the Grignard reagent (CH₃MgBr), the nucleophilic carbon of the Grignard reagent attacks the electrophilic carbon of the carbonyl group (C=O). **Reaction:** 1. **Nucleophilic attack:** The CH₃ group from CH₃MgBr attacks the carbonyl carbon, leading to the formation of a tetrahedral intermediate. 2. **Formation of Alkoxide:** The oxygen of the carbonyl group becomes negatively charged (alkoxide), and the magnesium bromide ion (MgBr) associates with it. ...
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