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Consider the following sequence of react...

Consider the following sequence of reactions
`underset((C_(4)H_(8)O_(3)))(A overset(CrO_(3))rarr B) overset("Warm")rarr CH_(3)overset(O) overset(||)C CH_(3)+CO_(2)`
The compound (A) is :

A

`HOCH_(2)CH_(2)CH_(2)COOH`

B

`CH_(3)CH(OH)CH_(2)COOH`

C

`CH_(3)CH_(2)CH(OH)COOH`

D

`(CH_(3))_(2)C(OH)COOH`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the compound (A) in the given sequence of reactions, we need to analyze the reactions step by step. ### Step 1: Understanding the Reaction Sequence The sequence begins with compound (A), which undergoes oxidation with CrO3 to form compound (B). Then, compound (B) is heated, resulting in the release of CO2 and the formation of a product that is a ketone. ### Step 2: Identifying the Nature of Compound (B) Since compound (B) is formed after the oxidation of compound (A) and is involved in a decarboxylation reaction, we can deduce that compound (B) must be a beta-keto carboxylic acid. This is because beta-keto carboxylic acids can undergo decarboxylation upon heating, releasing CO2. ### Step 3: Mechanism of Decarboxylation During decarboxylation, the beta-keto carboxylic acid loses CO2 to form an enol, which then tautomerizes to a more stable keto form. This confirms that compound (B) must have a structure that allows for this reaction. ### Step 4: Determining Compound (A) To find compound (A), we need to consider what could be oxidized by CrO3 to yield a beta-keto carboxylic acid. Since CrO3 is a strong oxidizing agent, compound (A) must contain a hydroxyl group (–OH) at the beta position relative to the carboxylic acid group. ### Step 5: Analyzing the Options We need to analyze the provided options to find a structure that fits the criteria: 1. **Option 1**: Does not have an –OH group at the beta position. 2. **Option 2**: Has an –OH group at the beta position, which can be oxidized to form a beta-keto carboxylic acid. 3. **Option 3**: Has an –OH group at the alpha position, which would not yield a beta-keto carboxylic acid. 4. **Option 4**: Similar to option 3, it has an –OH group at the alpha position. ### Conclusion The only option that fits the requirements for compound (A) is **Option 2**, which has an –OH group at the beta position. This will allow it to be oxidized to form the beta-keto carboxylic acid (B), which can then undergo decarboxylation to release CO2. ### Final Answer The compound (A) is **Option 2**. ---
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