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The correct statement(s) about the follo...

The correct statement(s) about the following reaction sequence is (are)
Cumene `(C_(9)H_(12))underset((ii)H_(3)O^(+))overset((i)O_(2))rarrPoverset(CHCl_(3)//NaOH)rarr`
Q(major)+R(minor), `Q underset(PhCH_(2)Br)overset(NaOH)rarrS`

A

R is steam volatile

B

Q gives dark violet coloration with `1%` aqueous `FeCl_(3)` solution

C

S gives yellow precipitate with 2,4-dinitrophenyhydrazine

D

S gives dark violet coloration with `1%` aqueous `FeCl_(3)` solution

Text Solution

AI Generated Solution

The correct Answer is:
To analyze the reaction sequence involving cumene and identify the correct statements, we will break down the steps involved in the reactions and the products formed. ### Step-by-Step Solution: 1. **Identify Cumene Structure**: - Cumene is isopropyl benzene, with the molecular formula \(C_9H_{12}\). Its structure can be represented as: \[ \text{C}_6\text{H}_5\text{C}(\text{CH}_3)_2 \] 2. **Reaction with Oxygen**: - When cumene is treated with oxygen (\(O_2\)), it undergoes oxidation. This reaction typically leads to the formation of hydroperoxide intermediates. 3. **Hydrolysis of the Hydroperoxide**: - The hydroperoxide formed from the oxidation of cumene is then treated with \(H_3O^+\) (acidic hydrolysis). This step cleaves the hydroperoxide, resulting in the formation of phenol and acetone: \[ \text{Cumene} + O_2 \xrightarrow{H_3O^+} \text{Phenol (P)} + \text{Acetone} \] 4. **Riemann-Tiemann Reaction**: - The phenol (P) is then treated with chloroform (\(CHCl_3\)) and sodium hydroxide (\(NaOH\)). This is a Riemann-Tiemann reaction, which generates a carbene intermediate. The reaction leads to the formation of two products: one is the major product (Q) and the other is the minor product (R). - The major product (Q) is typically the ortho-substituted product due to the activating nature of the phenolic group, while the minor product (R) is the para-substituted product. 5. **Formation of Products Q and R**: - The major product (Q) is salicylaldehyde (ortho-hydroxybenzaldehyde), and the minor product (R) is the para-hydroxybenzaldehyde. 6. **Further Reaction of Q**: - The major product Q (salicylaldehyde) is then treated with benzyl bromide (\(PhCH_2Br\)) and sodium hydroxide (\(NaOH\)). This reaction is a Williamson ether synthesis, leading to the formation of compound S: \[ Q + PhCH_2Br \xrightarrow{NaOH} S \] ### Summary of Products: - **P**: Phenol + Acetone - **Q**: Salicylaldehyde (major product) - **R**: Para-hydroxybenzaldehyde (minor product) - **S**: Benzyl salicylate or similar ether product. ### Correct Statements: 1. **R is steam volatile**: This statement is incorrect because R, being a phenolic compound, exhibits strong intermolecular hydrogen bonding, which increases its boiling point and decreases its volatility. 2. **Q gives dark violet coloration with FeCl3**: This statement is correct because salicylaldehyde contains a phenolic group that forms a complex with FeCl3, resulting in a violet color. 3. **S gives yellow precipitation with 2,4-dinitrophenylhydrazine**: This statement is correct because S contains a carbonyl group, which reacts with 2,4-DNP to form a yellow precipitate. 4. **S gives violet coloration with 1% ferric chloride**: This statement is incorrect because S does not contain a phenolic group and thus cannot react with FeCl3 to give a violet color. ### Final Answer: The correct statements are **B and C**.
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