MCQEasyJEE 2023Alcohols

JEE Chemistry 2023 Question with Solution

Incorrect method of preparation for alcohols from the following is:

  • A

    Ozonolysis of alkene.

  • B

    Hydroboration-oxidation of alkene.

  • C

    Reaction of alkyl halide with aqueous NaOH.

  • D

    Reaction of Ketone with RMgBr followed by hydrolysis.

Answer

Correct answer:A

Step-by-step solution

Standard Method

Given: The question asks for the incorrect method of preparation of alcohols.

Find: Which option does not prepare an alcohol.

Evaluate each method using the solution discussion:

  1. Ozonolysis of alkene cleaves the C=C\text{C=C} bond and gives carbonyl compounds such as aldehydes or ketones, not alcohols.
CH2=CH2O3C=O+C=O\text{CH}_2=\text{CH}_2 \xrightarrow{\text{O}_3} \text{C}=\text{O} + \text{C}=\text{O}

So this is not a method for preparing alcohols.

  1. Hydroboration-oxidation of alkene gives an alcohol.

  2. Reaction of alkyl halide with aqueous NaOH gives alcohol by nucleophilic substitution.

R-X+NaOHR-OH+NaX\text{R-X} + \text{NaOH} \rightarrow \text{R-OH} + \text{NaX}
  1. Reaction of ketone with RMgBr followed by hydrolysis gives an alcohol after Grignard addition.
R2C=O+RMgBrH2OR2C(OH)R\text{R}_2\text{C}=\text{O} + \text{RMgBr} \xrightarrow{\text{H}_2\text{O}} \text{R}_2\text{C(OH)R}

Therefore, the incorrect method is Ozonolysis of alkene. The correct option is A.

The provided solution shows option D, but its own explanation concludes that ozonolysis of alkene is the incorrect method. Hence the derived answer is A.

Option-by-option analysis

Given: Four methods are listed for preparation of alcohols.

Find: The method that is incorrect.

  • Option A: Ozonolysis of alkene breaks the double bond and forms aldehydes or ketones. It does not normally prepare alcohols.
  • Option B: Hydroboration-oxidation converts an alkene into an alcohol, so this is correct.
  • Option C: Alkyl halide with aqueous NaOH undergoes substitution to form alcohol, so this is correct.
  • Option D: Ketone with RMgBr\text{RMgBr} followed by hydrolysis forms an alcohol, so this is correct.

Thus only Option A is incorrect.

Common mistakes

  • Confusing ozonolysis with hydration of alkenes. Ozonolysis cleaves the double bond to give carbonyl compounds, whereas hydration-type reactions convert alkenes into alcohols.

  • Assuming every reaction involving an alkene gives an alcohol. The reagent and reaction type must be checked: hydroboration-oxidation gives alcohol, but ozonolysis does not.

  • Forgetting that Grignard reagent + ketone + hydrolysis forms an alcohol. The carbonyl group is converted to an alcohol after nucleophilic addition and workup.

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