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In the given reaction CH(3)-cH(2)COOHove...

In the given reaction `CH_(3)-cH_(2)COOHoverset((i)CH_(3)Li" (excess)"(ii)H_(3)O^(o+))rarr [X]`
[X] will be

A

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

B

`CH_(3)-CH_(2)-overset(O)overset(||)C-CH_(3)`

C

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

D

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

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem step by step, we will analyze the reaction of propanoic acid (CH₃CH₂COOH) with excess methyl lithium (CH₃Li) and then hydrolyze the product. ### Step 1: Identify the starting material The starting material is propanoic acid, which has the structure: \[ \text{CH}_3\text{CH}_2\text{COOH} \] ### Step 2: Reaction with methyl lithium (CH₃Li) Methyl lithium is a strong nucleophile. When propanoic acid reacts with CH₃Li, the nucleophile (CH₃⁻) will attack the carbonyl carbon (C=O) of the carboxylic acid. This results in the formation of a lithium carboxylate intermediate. The reaction can be represented as: \[ \text{CH}_3\text{CH}_2\text{COOH} + \text{CH}_3\text{Li} \rightarrow \text{CH}_3\text{CH}_2\text{C(OH)(CH}_3)\text{O}^- \text{Li}^+ \] ### Step 3: Formation of the lithium carboxylate After the nucleophilic attack, we have a lithium carboxylate: \[ \text{CH}_3\text{CH}_2\text{C(OH)(CH}_3)\text{O}^- \text{Li}^+ \] ### Step 4: Second addition of methyl lithium Since the problem states that there is an excess of CH₃Li, we can add another equivalent of methyl lithium. The lithium carboxylate will undergo another nucleophilic attack by CH₃Li at the carbonyl carbon, leading to the formation of a tertiary alcohol. The reaction can be represented as: \[ \text{CH}_3\text{CH}_2\text{C(OH)(CH}_3)\text{O}^- \text{Li}^+ + \text{CH}_3\text{Li} \rightarrow \text{CH}_3\text{CH}_2\text{C(CH}_3)(OH)\text{O}^- \text{Li}^+ \] ### Step 5: Hydrolysis The final step involves hydrolyzing the lithium salt with an acid (H₃O⁺). This will convert the lithium carboxylate into the corresponding alcohol. The hydrolysis can be represented as: \[ \text{CH}_3\text{CH}_2\text{C(CH}_3)(OH)\text{O}^- \text{Li}^+ + \text{H}_3\text{O}^+ \rightarrow \text{CH}_3\text{CH}_2\text{C(CH}_3)(OH) + \text{Li}^+ + \text{OH}^- \] ### Step 6: Final product After hydrolysis, the final product (X) will be: \[ \text{CH}_3\text{CH}_2\text{C(OH)(CH}_3) \] This is 2-methyl-1-propanol. ### Summary The final product [X] is 2-methyl-1-propanol (or tert-butyl alcohol). ---
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