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Which of the following aldehydes forms a stable
hydrate ?
- a)Formaldehyde
- b)Acetaldehyde
- c)Trichlorocetaldehyde
- d)Propionaldehyde
Correct answer is option 'C'. Can you explain this answer?
Verified Answer
Which of the following aldehydes forms a stablehydrate ?a)Formaldehyde...
Chloral hydrate is stable not so much because the geminal diol is stabilized, but because the aldehyde form is destabilized as compared to, say, acetaldehyde (which also hydrates reversibly in acidic aqueous solution). The sp2 hybridized carbon in the aldehyde is very electron deficient, so it reacts with electron-rich nucleophiles (like water). Acetaldehyde, with a methyl group, slightly reduces the electron deficiency by "donating" some electron density. Trichloroacetaldehyde, however, cannot donate nearly as much electron density because the electronegative chlorine atoms are pulling electron density away from the already electron-deficient carbon, making it even more reactive.
Formaldehyde, like trichloroacetaldehyde, exists primarily as the diol form, and even oligomerizes and polymerizes with itself in the absence of water (1,3,5 trioxane and "paraformaldehyde"). Here the issue is not electronegativity (the hydrogen substituents are fairly electron-rich, and energetically favorable to share). Unfortunately, there is a symmetry mismatch in the orbitals involved, so it is impossible for the hydrogen substituents to ease the sp2 carbon's deficiency. Therefore, formaldehyde reacts with water, alcohols, proteins, even itself, to relieve the strain.
Most Upvoted Answer
Which of the following aldehydes forms a stablehydrate ?a)Formaldehyde...
Understanding Aldehydes and Their Hydrates
Aldehydes can react with water to form hydrates. However, the stability of these hydrates depends on the structure of the aldehyde and the presence of substituents.
Factors Influencing Hydrate Stability
- Electronic Effects: Electron-withdrawing groups enhance the stability of hydrates.
- Steric Hindrance: Bulky groups can hinder the formation of a stable hydrate.
Hydrate Formation in Aldehydes
1. Formaldehyde:
- Weakly stable hydrate (methanediol) due to lack of electron-withdrawing groups.
2. Acetaldehyde:
- Forms a hydrate, but it is less stable than others.
3. Trichloroacetaldehyde (Correct Answer):
- Contains three chlorine atoms, which are strong electron-withdrawing groups.
- The electron-withdrawing effect stabilizes the hydrate by increasing the positive charge on the carbonyl carbon, making it more reactive towards water.
- The resulting hydrate is much more stable due to the ability of chlorine atoms to stabilize the transition state during formation.
4. Propionaldehyde:
- Forms a hydrate, but lacks the strong electron-withdrawing groups found in trichloroacetaldehyde.
Conclusion
The correct answer is option 'C', trichloroacetaldehyde, as its electron-withdrawing chlorine atoms significantly stabilize the hydrate formation, making it more stable compared to the other aldehydes listed.
Aldehydes can react with water to form hydrates. However, the stability of these hydrates depends on the structure of the aldehyde and the presence of substituents.
Factors Influencing Hydrate Stability
- Electronic Effects: Electron-withdrawing groups enhance the stability of hydrates.
- Steric Hindrance: Bulky groups can hinder the formation of a stable hydrate.
Hydrate Formation in Aldehydes
1. Formaldehyde:
- Weakly stable hydrate (methanediol) due to lack of electron-withdrawing groups.
2. Acetaldehyde:
- Forms a hydrate, but it is less stable than others.
3. Trichloroacetaldehyde (Correct Answer):
- Contains three chlorine atoms, which are strong electron-withdrawing groups.
- The electron-withdrawing effect stabilizes the hydrate by increasing the positive charge on the carbonyl carbon, making it more reactive towards water.
- The resulting hydrate is much more stable due to the ability of chlorine atoms to stabilize the transition state during formation.
4. Propionaldehyde:
- Forms a hydrate, but lacks the strong electron-withdrawing groups found in trichloroacetaldehyde.
Conclusion
The correct answer is option 'C', trichloroacetaldehyde, as its electron-withdrawing chlorine atoms significantly stabilize the hydrate formation, making it more stable compared to the other aldehydes listed.
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Which of the following aldehydes forms a stablehydrate ?a)Formaldehydeb)Acetaldehydec)Trichlorocetaldehyded)PropionaldehydeCorrect answer is option 'C'. Can you explain this answer?
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Which of the following aldehydes forms a stablehydrate ?a)Formaldehydeb)Acetaldehydec)Trichlorocetaldehyded)PropionaldehydeCorrect answer is option 'C'. Can you explain this answer? for JEE 2025 is part of JEE preparation. The Question and answers have been prepared according to the JEE exam syllabus. Information about Which of the following aldehydes forms a stablehydrate ?a)Formaldehydeb)Acetaldehydec)Trichlorocetaldehyded)PropionaldehydeCorrect answer is option 'C'. Can you explain this answer? covers all topics & solutions for JEE 2025 Exam. Find important definitions, questions, meanings, examples, exercises and tests below for Which of the following aldehydes forms a stablehydrate ?a)Formaldehydeb)Acetaldehydec)Trichlorocetaldehyded)PropionaldehydeCorrect answer is option 'C'. Can you explain this answer?.
Which of the following aldehydes forms a stablehydrate ?a)Formaldehydeb)Acetaldehydec)Trichlorocetaldehyded)PropionaldehydeCorrect answer is option 'C'. Can you explain this answer? for JEE 2025 is part of JEE preparation. The Question and answers have been prepared according to the JEE exam syllabus. Information about Which of the following aldehydes forms a stablehydrate ?a)Formaldehydeb)Acetaldehydec)Trichlorocetaldehyded)PropionaldehydeCorrect answer is option 'C'. Can you explain this answer? covers all topics & solutions for JEE 2025 Exam. Find important definitions, questions, meanings, examples, exercises and tests below for Which of the following aldehydes forms a stablehydrate ?a)Formaldehydeb)Acetaldehydec)Trichlorocetaldehyded)PropionaldehydeCorrect answer is option 'C'. Can you explain this answer?.
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