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Aldehydes Ketones and Carboxylic Acids question

2025 · 7 Apr · Shift 2 · Q8
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Aldehydes Ketones and Carboxylic Acids question

2025 · 7 Apr · Shift 2 · Q8

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
" P " is an optically active compound with molecular formula C6H12O\mathrm{C}_6 \mathrm{H}_{12} \mathrm{O}C6​H12​O. When ' P ' is treated with 2, 4-dinitrophenylhydrazine, it gives a positive test. However, in presence of Tollens reagent, " P " gives a negative test. Predict the structure of " P ".
  1. A
    JEE Main 2025 (Online) 7th April Evening Shift Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 7 English Option 1
  2. B
    JEE Main 2025 (Online) 7th April Evening Shift Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 7 English Option 2
  3. C
    JEE Main 2025 (Online) 7th April Evening Shift Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 7 English Option 3
  4. D
    JEE Main 2025 (Online) 7th April Evening Shift Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 7 English Option 4
View written solutionFree

Correct answer: B

  1. Use the molecular formula to find unsaturation

Given compound PPP has formula C6H12O\mathrm{C_6H_{12}O}C6​H12​O.

Degree of unsaturation:

DU=2C+2−H2=2(6)+2−122=14−122=1\text{DU} = \frac{2C+2-H}{2} = \frac{2(6)+2-12}{2} = \frac{14-12}{2} = 1DU=22C+2−H​=22(6)+2−12​=214−12​=1

So, PPP has one degree of unsaturation.

  1. Interpret the 2,4-DNP test

A positive 2,4-dinitrophenylhydrazine test indicates the presence of a carbonyl group (>C=O>C=O>C=O), so PPP is either an aldehyde or a ketone.

  1. Interpret the Tollens test

PPP gives a negative Tollens test, so it is not an aldehyde. Therefore, PPP must be a ketone.

  1. Use optical activity condition

PPP is stated to be optically active, so it must contain at least one chiral carbon.

Thus we need a compound with:

  • formula C6H12O\mathrm{C_6H_{12}O}C6​H12​O
  • a ketone functional group
  • at least one chiral center
  1. Find a suitable ketone isomer

Acyclic saturated ketones with formula C6H12O\mathrm{C_6H_{12}O}C6​H12​O are possible. We need one having a stereogenic center.

A suitable structure is:

CH3COCH(CH3)CH2CH3\mathrm{CH_3COCH(CH_3)CH_2CH_3}CH3​COCH(CH3​)CH2​CH3​

This is 3-methyl-2-pentanone.

Check chirality at the carbon CH(CH3)\mathrm{CH(CH_3)}CH(CH3​): It is attached to four different groups:

  • H\mathrm{H}H
  • CH3\mathrm{CH_3}CH3​
  • CH2CH3\mathrm{CH_2CH_3}CH2​CH3​
  • COCH3\mathrm{COCH_3}COCH3​

Hence this carbon is chiral, so the compound is optically active.

  1. Conclusion

Therefore, PPP must be 3-methyl-2-pentanone, which corresponds to option B.

  1. Comparison with stored answer

Stored correct answer is B. My derived answer is also B, so they agree.

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