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An unknown compound on ozonolysis to giv...

An unknown compound on ozonolysis to give acid `C_(3)H_(6)O_(2)` and a ketone `C_(4)H_(8)O`. From this information identify structure of unknown compound.

A

`(CH_(3))_(2)C=CHCH_(2)-CH_(2)CH_(3)`

B

`CH_(3)CH_(2)-overset(CH_(3))overset(|)(C )=CHCH_(2)CH_(3)`

C

`(CH_(3))_(2)CHCH=CHCH_(2)CH_(3)`

D

`CH_(3)CH_(2)CH_(2)CH=CHCH_(2)CH_(2)`

Text Solution

AI Generated Solution

The correct Answer is:
To identify the structure of the unknown compound that gives an acid (C₃H₆O₂) and a ketone (C₄H₈O) upon ozonolysis, we can follow these steps: ### Step 1: Understand Ozonolysis Ozonolysis is a reaction where ozone (O₃) cleaves double bonds in alkenes, leading to the formation of carbonyl compounds (aldehydes or ketones) and/or carboxylic acids. ### Step 2: Analyze the Products We know that the ozonolysis of the unknown compound produces: - An acid with the formula C₃H₆O₂ - A ketone with the formula C₄H₈O ### Step 3: Determine the Structure of the Acid The acid C₃H₆O₂ can be identified as propanoic acid (CH₃CH₂COOH). This indicates that the ozonolysis must involve a double bond that, when cleaved, results in a three-carbon chain leading to a carboxylic acid. ### Step 4: Determine the Structure of the Ketone The ketone C₄H₈O can be identified as butanone (CH₃COCH₂CH₃). This indicates that the ozonolysis must also involve a double bond that, when cleaved, results in a four-carbon chain leading to a ketone. ### Step 5: Construct Possible Structures To find the unknown compound, we need to consider a structure that has both a double bond and can yield both the identified acid and ketone upon ozonolysis. ### Step 6: Testing Possible Structures Let's analyze the options provided in the video transcript: 1. **Option A**: Yields a ketone with only 3 carbons. 2. **Option B**: Yields both the desired acid (C₃H₆O₂) and ketone (C₄H₈O). 3. **Option C**: Yields aldehydes, not a ketone. 4. **Option D**: Yields aldehydes, not a ketone. From the analysis, **Option B** is the only one that produces both the required acid and ketone. ### Conclusion The structure of the unknown compound is represented by **Option B**, which upon ozonolysis gives propanoic acid (C₃H₆O₂) and butanone (C₄H₈O). ---
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RESONANCE ENGLISH-STRUCTURAL IDENTIFICATION-Exercise-1 (Part-II)
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