Convert the following: (i) acetaldehyde to isopropyl alcohol. (ii) cumene to phenol. (iii) anisole to phenol.

Question 61 of 66

Q. Convert the following:

(i) acetaldehyde to isopropyl alcohol.

(ii) cumene to phenol.

(iii) anisole to phenol. Write two uses of neon.

Maharashtra MsbshseMaharashtra HSC (MSBSHSE) Board 2024Subjective· 4mImportance★★★★★

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Acetaldehyde→isopropanol via Grignard; cumene→phenol+acetone (cumene process); anisole→phenol via HI cleavage; neon used in discharge/advertising lamps and lightning arrestors.

Acetaldehyde to isopropyl alcohol: Grignard addition of methylmagnesium bromide to the aldehyde carbonyl, followed by acid hydrolysis: $CH_3CHO + CH_3MgBr \longrightarrow CH_3CH(OMgBr)CH_3 \xrightarrow{H_3O^+} CH_3CH(OH)CH_3$
Cumene to phenol (cumene process): cumene (isopropylbenzene) is air-oxidised to cumene hydroperoxide, which is cleaved by dilute acid to phenol and acetone as a co-product: $C_6H_5CH(CH_3)_2 \xrightarrow{O_2} C_6H_5C(CH_3)_2OOH \xrightarrow{dil.\ H_2SO_4} C_6H_5OH + CH_3COCH_3$
Anisole to phenol: demethylation of the ether by refluxing with concentrated HI, cleaving the weaker $O-CH_3$ bond: $C_6H_5OCH_3 + HI \longrightarrow C_6H_5OH + CH_3I$ …

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Same / Similar Concept — real previous-year questions on the same or a closely similar concept, not this exact question.

CBSE 2025Set X11 markMCQ
$Q. Cumene hydroperoxide on hydrolysis with dilute acid gives ______.$
(a) alcohol and phenol
(b) only phenol
(c) phenol and acetone
(d) alcohol and acetone
›Reveal solutionSolution

Cumene hydroperoxide, on hydrolysis with dilute acid, cleaves to give phenol and acetone (the industrial "cumene process" for phenol).

In the industrial cumene process, cumene (isopropylbenzene) is air-oxidised to cumene hydroperoxide, $\text{C}_6\text{H}_5\text{C(CH}_3)_2\text{OOH}$ . Treatment with dilute acid then cleaves it: …
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CBSE 2023Set ANNUAL1 markMCQ
$Q. In reaction of manufacturation of phenol from cumene the by-product is$
(a) Tribromophenol
(b) Benzoquenone
(c) Picric acid
(d) Acetone
›Reveal solutionSolution

In the industrial cumene process, oxidation of cumene followed by acid hydrolysis of the hydroperoxide yields both phenol and acetone.

Cumene (isopropylbenzene) is air-oxidised to cumene hydroperoxide. Treating this hydroperoxide with dilute acid causes rearrangement and cleavage to give phenol as the main product, with acetone (propan-2-one …

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CBSE 2022Set ANNUAL1 markMCQ
$Q. Isopropylbenzene on air oxidation followed by decomposition by dilute acid gives _____.$
(a) $C_6H_5OH$
(b) $C_6H_5COOCH_3$
(c) $C_6H_5COOH$
(d) $C_6H_5CHO$
›Reveal solutionSolution

Air oxidation of cumene followed by acid cleavage is the industrial cumene process for making phenol.

Isopropylbenzene (cumene) is air-oxidised to cumene hydroperoxide, which on treatment with dilute acid undergoes rearrangement/cleavage to give phenol and acetone as a co-product: …

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