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CH(3)-CH(2)-overset(O)overset(||)C-O Ag ...

`CH_(3)-CH_(2)-overset(O)overset(||)C-O Ag overset(Br_(2))underset("CCl"_(4))rarrX overset("(1) Li")underset("(2) CuI")rarr Y overset(CH_(3)-CH_(2)-Br)underset("dry ether")rarr Z`

A

`CH_(3)-CH_(3)`

B

`CH_(3)-CH_(2)-CH_(3)`

C

`CH_(3)-cH_(2)-CH_(2)-CH_(3)`

D

`CH_(3)-overset(CH_(3))overset("| ")"CH"-CH_(3)`.

Text Solution

AI Generated Solution

The correct Answer is:
To solve the given question step by step, we will analyze each reaction and its corresponding product. ### Step 1: Initial Reaction We start with silver propionate, which is represented as: \[ \text{CH}_3\text{CH}_2\text{C}(=O)\text{Ag} \] This compound is treated with bromine (\( \text{Br}_2 \)) in the presence of carbon tetrachloride (\( \text{CCl}_4 \)). This reaction is known as the Hans-Dekker reaction. **Mechanism:** 1. The oxygen atom in the silver propionate acts as a nucleophile and attacks the carbon atom of the carbonyl group, leading to the formation of a brominated product. 2. The silver ion (\( \text{Ag}^+ \)) is released as \( \text{AgBr} \). The product after this reaction can be represented as: \[ \text{CH}_3\text{CH}_2\text{C}(=O)\text{OBr} \] ### Step 2: Formation of Free Radicals The bromine atom can then dissociate, leading to the formation of free radicals: 1. The \( \text{OBr} \) can break down to form a free radical \( \text{O}^\cdot \) and \( \text{Br}^\cdot \). 2. The carbonyl group can lose carbon dioxide (\( \text{CO}_2 \)), leading to the formation of a radical. This results in: \[ \text{CH}_3\text{CH}_2\cdot + \text{Br}^\cdot \] ### Step 3: Product X The combination of the ethyl radical and bromine radical gives us product X: \[ \text{Product X: CH}_3\text{CH}_2\text{Br} \] ### Step 4: Treatment with Lithium and Copper Iodide Product X is then treated with lithium (\( \text{Li} \)) and copper iodide (\( \text{CuI} \)). This reaction is known as the Corey-House synthesis, which is used to prepare Gilman's reagent. **Mechanism:** 1. Lithium replaces the bromine in the ethyl bromide, forming ethyl lithium: \[ \text{CH}_3\text{CH}_2\text{Li} \] 2. The copper iodide facilitates the formation of the Gilman's reagent: \[ \text{CH}_3\text{CH}_2\text{CuLi} \] ### Step 5: Reaction with Alkyl Halide Now, the Gilman's reagent is treated with another alkyl halide, which is \( \text{CH}_3\text{CH}_2\text{Br} \). **Mechanism:** 1. The nucleophilic ethyl group from the Gilman's reagent attacks the alkyl halide, leading to the formation of a new carbon-carbon bond. 2. The bromine is displaced. The final product Y can be represented as: \[ \text{Product Y: CH}_3\text{CH}_2\text{CH}_2\text{CH}_3 \] ### Final Product Z Thus, the final product Z is: \[ \text{Z: CH}_3\text{CH}_2\text{CH}_2\text{CH}_3 \] This corresponds to butane. ### Summary of Products - **Product X:** \( \text{CH}_3\text{CH}_2\text{Br} \) - **Product Y:** \( \text{CH}_3\text{CH}_2\text{CuLi} \) - **Final Product Z:** \( \text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_3 \) (Butane)
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