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Alcoholoverset(P + I2)(rarr)X overset(Mg...

Alcohol`overset(P + I_2)(rarr)X overset(Mg, dry,"ether")(rarr)Y overset(HCHO)(rarr)Z overset(H_2O //H^+)(rarr)2`- methylpropanol
In this sequence of reaction, the starting alcohol is

A

ethanol

B

propan-2-ol

C

propanol

D

butan-2-ol

Text Solution

AI Generated Solution

The correct Answer is:
To determine the starting alcohol in the given sequence of reactions, we will analyze each step carefully. ### Step 1: Identify the Reactions The sequence of reactions is as follows: 1. Alcohol `ROH` reacts with phosphorus and iodine (`P + I2`) to form an alkyl iodide `RI`. 2. The alkyl iodide `RI` reacts with magnesium in dry ether to form a Grignard reagent `R-MgI`. 3. The Grignard reagent `R-MgI` reacts with formaldehyde (`HCHO`) to form an alcohol `R-CH2OH`. 4. The alcohol undergoes hydrolysis in the presence of water and acid (`H2O/H^+`) to yield a secondary alcohol, which is `2-methylpropanol`. ### Step 2: Analyze the Final Product The final product is `2-methylpropanol`, which has the structure: - **2-methylpropanol**: This compound has a total of 4 carbon atoms (C4) and an alcohol functional group (-OH) at the second carbon. ### Step 3: Determine the Structure of the Starting Alcohol To find the starting alcohol `ROH`, we need to trace back from the final product: - The Grignard reagent `R-MgI` must have been formed from an alkyl iodide `RI`, which in turn was derived from the starting alcohol `ROH`. - The reaction of the Grignard reagent with formaldehyde (`HCHO`) adds one carbon to the structure. Therefore, if the product after this reaction is `R-CH2OH`, then `R` must be a carbon chain that, when combined with the carbon from formaldehyde, results in a total of 4 carbons in `2-methylpropanol`. ### Step 4: Identify the Alkyl Group Since the final product is `2-methylpropanol`, we can deduce that: - The Grignard reagent must have been derived from an alkyl iodide that has 3 carbons (C3) because the addition of one carbon from formaldehyde results in a total of 4 carbons. - The alkyl iodide must have been formed from the starting alcohol, which is `propan-2-ol` (or `isopropanol`), because it has the structure necessary to yield the 3-carbon alkyl iodide upon reaction with phosphorus and iodine. ### Conclusion Thus, the starting alcohol is **propan-2-ol** (or isopropanol). ### Final Answer The starting alcohol is **propan-2-ol**. ---
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