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Aldehydes Ketones and Carboxylic Acids question

2007 · Shift 2 · Q6
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  5. /2007 · Shift 2 · Q6

Aldehydes Ketones and Carboxylic Acids question

2007 · Shift 2 · Q6

JEE AdvancedChemistryAldehydes Ketones and Carboxylic AcidsMCQ+3 / −1
Cyclohexene on ozonolysis followed by reaction with zinc dust and water gives compound E. Compound E on further treatment with aqueous KOH yields compound F. Compound F is :
  1. A
  2. B
  3. C
  4. D
View written solutionFree

Correct answer: A

  1. Ozonolysis of cyclohexene

Cyclohexene has one double bond inside a six-membered ring. On ozonolysis followed by reductive workup with Zn/H2O\text{Zn}/\text{H}_2\text{O}Zn/H2​O, the double bond is cleaved and each alkene carbon becomes an aldehyde.

Thus, cyclohexene gives the open-chain dialdehyde:

OHC−(CH2)4−CHO\text{OHC}-(\text{CH}_2)_4-\text{CHO}OHC−(CH2​)4​−CHO

This compound is hexane-1,6-dial (adipaldehyde). Let this be compound EEE.


  1. Reaction of EEE with aqueous KOH

Now EEE is a dialdehyde having α\alphaα-hydrogens. In aqueous KOH, it undergoes intramolecular aldol condensation because the two aldehyde groups are present in the same molecule and can cyclize.

Structure of EEE:

OHC−CH2−CH2−CH2−CH2−CHO\text{OHC}-\text{CH}_2-\text{CH}_2-\text{CH}_2-\text{CH}_2-\text{CHO}OHC−CH2​−CH2​−CH2​−CH2​−CHO

An enolate formed at one end attacks the aldehyde at the other end, producing a cyclic β\betaβ-hydroxy aldehyde. Since there are 6 carbons total, ring closure gives a 5-membered ring.

After aldol cyclization (and the usual dehydration tendency in base), the product is cyclopent-1-enecarbaldehyde.

So compound FFF is:

cyclopent-1-enecarbaldehyde\boxed{\text{cyclopent-1-enecarbaldehyde}}cyclopent-1-enecarbaldehyde​


  1. Conclusion

Therefore, the correct option is the one corresponding to cyclopent-1-enecarbaldehyde, which is given as Option A.


  1. Comparison with stored answer

Stored correct answer = A.

Our derived answer = A.

Hence, the derived answer agrees with the stored answer.

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