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A compound [A] has the formula C(4)H(8)O...

A compound [A] has the formula `C_(4)H_(8)O_(2)`. When reacted with a Grignard reagent, `CH_(3)MgBr`, it takes up two molecules of it and upon acidification gives an alcohol [B]. The alcohol on reacting with Lucas reagent gives white coludiness on standing for sometime. When the alochol is oxidised, a compound [C] is produced with a pleasant smell. It neither reacts with Tollen's reagent, nor with Fehling's reagent.
The compound [A] is

A

n-propyl formate

B

ethylacetate

C

methylpropionate

D

None of these.

Text Solution

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The correct Answer is:
To determine the compound [A] with the formula \( C_4H_8O_2 \), we can follow these steps: ### Step 1: Analyze the Molecular Formula The molecular formula \( C_4H_8O_2 \) suggests that the compound could be an ester or a carboxylic acid. ### Step 2: Reaction with Grignard Reagent The compound reacts with the Grignard reagent \( CH_3MgBr \) and takes up two molecules of it. This indicates that the compound is likely an ester, as esters typically react with Grignard reagents to form alcohols. ### Step 3: Identify the Structure of Compound [A] Given that the compound takes up two molecules of the Grignard reagent, we can deduce that it is likely a simple ester. The structure can be represented as: - An ester formed from formic acid and an alcohol. A possible structure for compound [A] is: \[ CH_3OCOCH_2CH_3 \] This is N-propyl formate. ### Step 4: Formation of Alcohol [B] Upon acidification, the ester reacts to form a secondary alcohol [B]. The reaction can be summarized as: \[ RCOOR' + 2 CH_3MgBr \rightarrow RCH(OH)R' + MgBr(OR') \] ### Step 5: Reaction with Lucas Reagent The alcohol [B] gives white cloudiness when reacted with Lucas reagent, indicating that it is a secondary alcohol. This is consistent with the expected product from the reaction of the Grignard reagent with the ester. ### Step 6: Oxidation of Alcohol [B] When the alcohol [B] is oxidized, it produces compound [C], which has a pleasant smell. This suggests that compound [C] is likely an ester or a ketone. ### Step 7: Reactivity with Tollen's and Fehling's Reagents The compound [C] does not react with Tollen's reagent or Fehling's reagent, indicating that it is not an aldehyde or a reducing sugar. This further supports the idea that [C] is likely an ester or a ketone. ### Conclusion Based on the analysis, the compound [A] is identified as: **N-propyl formate (CH3OCOCH2CH3)**.

To determine the compound [A] with the formula \( C_4H_8O_2 \), we can follow these steps: ### Step 1: Analyze the Molecular Formula The molecular formula \( C_4H_8O_2 \) suggests that the compound could be an ester or a carboxylic acid. ### Step 2: Reaction with Grignard Reagent The compound reacts with the Grignard reagent \( CH_3MgBr \) and takes up two molecules of it. This indicates that the compound is likely an ester, as esters typically react with Grignard reagents to form alcohols. ...
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