JEE AdvancedChemistryHydrocarbonsMCQ+3 / −1
The major product of the following reaction is 

- Aa hemiacetal
- Ban acetal
- Can ether
- Dan ester
View written solutionFree
Correct answer: B
Step-by-step solution:
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Identify the Reactants and Reaction Conditions:
- The first reactant is 5-hydroxy-2-pentanone. It has two functional groups: a ketone (C=O) at the C-2 position and a primary alcohol (-OH) at the C-5 position.
- The second reactant is ethylene glycol (HO-CH₂-CH₂-OH), which is a diol (an alcohol with two hydroxyl groups).
- The reaction is carried out in the presence of an acid catalyst, denoted by H⁺.
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Recognize the Type of Reaction:
- The reaction between a ketone and an alcohol in the presence of an acid catalyst is a classic reaction for the formation of an acetal (or more specifically, a ketal, since the starting carbonyl is a ketone).
- Ethylene glycol is commonly used as a protecting group for aldehydes and ketones because it forms a stable five-membered cyclic acetal.
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Analyze the Reactivity of the Functional Groups:
- The ketone group is highly reactive towards nucleophilic attack, especially after its oxygen is protonated by the acid catalyst. This makes the carbonyl carbon very electrophilic.
- The alcohol groups (both in 5-hydroxy-2-pentanone and ethylene glycol) are nucleophilic.
- The reaction will preferentially occur at the more reactive site, which is the ketone's carbonyl carbon.
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Outline the Reaction Mechanism:
- Step a: Protonation: The acid catalyst (H⁺) protonates the oxygen of the ketone group, increasing the electrophilicity of the carbonyl carbon.
- Step b: Nucleophilic Attack (Hemiacetal formation): One of the hydroxyl groups of ethylene glycol acts as a nucleophile and attacks the protonated carbonyl carbon. After deprotonation, a hemiacetal intermediate is formed.
- Step c: Protonation and Water Elimination: The hydroxyl group of the hemiacetal is protonated by H⁺, forming a good leaving group (H₂O). Water is eliminated, generating a resonance-stabilized carbocation (an oxonium ion).
- Step d: Intramolecular Nucleophilic Attack (Acetal formation): The second hydroxyl group of the ethylene glycol moiety attacks the carbocationic carbon in an intramolecular fashion, closing the ring.
- Step e: Deprotonation: A final deprotonation step regenerates the acid catalyst and yields the final product, a cyclic acetal.
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Determine the Structure of the Major Product:
- The C=O double bond of the ketone is replaced by two single bonds to the oxygen atoms of the ethylene glycol. This forms a five-membered ring known as a 1,3-dioxolane ring, attached to the C-2 of the original pentanone chain.
- The hydroxyl group at the C-5 position of the starting material does not participate in this primary reaction and remains unchanged.
- The functional group formed at the C-2 position is characterized by a carbon atom bonded to two alkoxy (-OR) groups. This functional group is defined as an acetal.
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Evaluate the Given Options:
- A: a hemiacetal: A hemiacetal has one -OH group and one -OR group on the same carbon. This is an intermediate, not the final major product under these conditions.
- B: an acetal: The final product has a carbon atom (C-2) bonded to two alkoxy groups, forming a cyclic structure. This is the definition of a cyclic acetal. This is the correct description of the major product.
- C: an ether: An ether has the general structure R-O-R'. While the acetal contains ether linkages, the specific functional group formed from the ketone is an acetal, which is a more precise classification.
- D: an ester: An ester (R-COO-R') is formed from a carboxylic acid and an alcohol. The starting material is a ketone, so an ester cannot be the product.
Conclusion: The reaction of 5-hydroxy-2-pentanone with ethylene glycol in the presence of an acid catalyst forms a cyclic acetal as the major product. Therefore, option B is the correct answer.
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