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Alcohol (X)overset("aq. NaOH"+I(2))rarrC...

Alcohol `(X)overset("aq. NaOH"+I_(2))rarrCHI_(3)+(Y)overset(H_(3)O^(+))rarrPhCH_(2)COOH`. The alcohol (X) is

A

`CH_(3)underset(Ph)underset("| ")"CH"CH(OH)CH_(2)`

B

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

C

`PhCH(OH)CH_(2)CH_(3)`

D

`PhCH(CH_(3))OH`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, we need to identify the alcohol (X) that undergoes a reaction to form iodoform (CHI3) and then, through acid hydrolysis, produces a carboxylic acid (PhCH2COOH). ### Step-by-Step Solution: 1. **Understanding the Reaction**: - The reaction involves an alcohol (X) reacting with aqueous sodium hydroxide (NaOH) and iodine (I2) to produce iodoform (CHI3) and another compound (Y). - The compound Y is then subjected to acid hydrolysis to yield PhCH2COOH. 2. **Identifying the Type of Reaction**: - The reaction of alcohol with NaOH and iodine is characteristic of the iodoform reaction, which typically occurs with methyl alcohols or alcohols that can be oxidized to form a methyl ketone. 3. **Formulating Alcohol (X)**: - For the iodoform reaction to occur, the alcohol must have the structure that allows for the formation of a methyl ketone. - The general structure of alcohol (X) can be represented as R-CH(OH)-CH3, where R is a phenyl group (Ph). 4. **Choosing the Correct Alcohol**: - Given that Y is PhCH2COOH, we can deduce that the alcohol (X) must be Ph-CH(OH)-CH3. - This structure allows the formation of a methyl ketone (Ph-CO-CH3) upon oxidation, which can then react with NaOH and iodine to form iodoform. 5. **Confirming the Reaction Pathway**: - When Ph-CH(OH)-CH3 reacts with NaOH and iodine, it is oxidized to form the corresponding methyl ketone (Ph-CO-CH3). - This methyl ketone can then undergo the iodoform reaction to yield iodoform (CHI3) and the sodium salt of the carboxylic acid (Ph-CH2COONa). - Upon acid hydrolysis of the sodium salt, we obtain the desired carboxylic acid, PhCH2COOH. 6. **Conclusion**: - Therefore, the alcohol (X) is Ph-CH(OH)-CH3. ### Final Answer: The alcohol (X) is **Ph-CH(OH)-CH3**.
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