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Which of the following compound have lar...

Which of the following compound have larger `C-O` bond length than `C-O` bond length of `H_(3)-overset(O)overset(||)(C)-CH_(3)`?

A

B

C

D

Text Solution

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The correct Answer is:
To determine which of the given compounds has a larger C-O bond length than the C-O bond length in acetone (H₃C-C(=O)-CH₃), we need to analyze the polarization and resonance effects in each compound. Here’s a step-by-step solution: ### Step 1: Understand the C-O Bond in Acetone - Acetone has a carbonyl group (C=O) where the carbon is bonded to two methyl groups (−CH₃). - The C=O bond in acetone is a double bond, which typically has a shorter bond length compared to a single bond (C-O). ### Step 2: Identify Factors Affecting Bond Length - The C-O bond length can increase if there is a polarization that leads to a partial positive charge on carbon and a partial negative charge on oxygen. - Resonance stabilization can also affect the bond length. If resonance allows for the delocalization of charges, it may lead to a longer bond length. ### Step 3: Analyze Each Option 1. **Option A**: Analyze the structure and polarization. - If polarization occurs, it creates a negative charge on oxygen and a positive charge on carbon. The presence of conjugation and following Huckel's rule (4n + 2 pi electrons) stabilizes the structure, potentially leading to a longer C-O bond length than in acetone. 2. **Option B**: Analyze the structure and polarization. - Similar polarization occurs, but this compound does not follow Huckel's rule (it has 4 pi electrons). Anti-aromatic compounds are less stable and do not favor polarization, leading to a shorter C-O bond length. Thus, this option can be eliminated. 3. **Option C**: Analyze the structure and polarization. - Polarization leads to resonance stabilization. The resonance structures allow for the delocalization of charges, which can result in a longer C-O bond length compared to acetone. 4. **Option D**: Analyze the structure and polarization. - This compound also shows polarization, but it has fewer alpha-hydrogens compared to acetone, making it less stable. Therefore, it is less likely to favor polarization, leading to a shorter C-O bond length than acetone. This option can be eliminated. ### Step 4: Conclusion - The compounds that have a larger C-O bond length than acetone are **Option A** and **Option C** based on their ability to stabilize polarization and resonance. ### Final Answer: **Option A and Option C have larger C-O bond lengths than acetone.** ---
To determine which of the given compounds has a larger C-O bond length than the C-O bond length in acetone (H₃C-C(=O)-CH₃), we need to analyze the polarization and resonance effects in each compound. Here’s a step-by-step solution: ### Step 1: Understand the C-O Bond in Acetone - Acetone has a carbonyl group (C=O) where the carbon is bonded to two methyl groups (−CH₃). - The C=O bond in acetone is a double bond, which typically has a shorter bond length compared to a single bond (C-O). ### Step 2: Identify Factors Affecting Bond Length - The C-O bond length can increase if there is a polarization that leads to a partial positive charge on carbon and a partial negative charge on oxygen. ...
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