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Aldehydes Ketones and Carboxylic Acids question

2020 · 4 Sep · Shift 1 · Q14
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Aldehydes Ketones and Carboxylic Acids question

2020 · 4 Sep · Shift 1 · Q14

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
An organic compound (A) (molecular formula C6H12O2C_6H_{12}O_2C6​H12​O2​) was hydrolysed with dil. H2SO4H_2SO_4H2​SO4​ to give a carboxylic acid (B) and an alcohol (C). ‘C’ gives white turbidity immediately when treated with anhydrous ZnCl2ZnCl_2ZnCl2​ and conc. HClHClHCl. The organic compound (A) is :
  1. A
    JEE Main 2020 (Online) 4th September Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 169 English Option 1
  2. B
    JEE Main 2020 (Online) 4th September Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 169 English Option 2
  3. C
    JEE Main 2020 (Online) 4th September Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 169 English Option 3
  4. D
    JEE Main 2020 (Online) 4th September Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 169 English Option 4
View written solutionFree

Correct answer: D

  1. Identify the functional class of AAA

Since AAA on hydrolysis with dilute H2SO4H_2SO_4H2​SO4​ gives a carboxylic acid and an alcohol, AAA must be an ester.

So, A=RCOOR′A = RCOOR'A=RCOOR′ with molecular formula C6H12O2C_6H_{12}O_2C6​H12​O2​


  1. Use the test for alcohol CCC

Alcohol CCC gives white turbidity immediately with anhydrous ZnCl2ZnCl_2ZnCl2​ and concentrated HClHClHCl (Lucas reagent).

This means CCC is a tertiary alcohol, because tertiary alcohols react immediately in the Lucas test.

Now, among alcohols formed by hydrolysis of an ester, the alcohol part must come from the alkoxy group R′OHR'OHR′OH.

The only common tertiary alcohol with small carbon number is: tert-butyl alcohol=(CH3)3COHtert\text{-}butyl\ alcohol = (CH_3)_3COHtert-butyl alcohol=(CH3​)3​COH which has formula C4H10OC_4H_{10}OC4​H10​O


  1. Find the acid part using molecular formula

Total formula of ester AAA is: C6H12O2C_6H_{12}O_2C6​H12​O2​

If the alcohol obtained is tert-butyl alcohol (C4H10OC_4H_{10}OC4​H10​O), then the acid part should contribute 2 carbons in the ester.

The corresponding ester is formed from:

  • alcohol part: tertterttert-butyl group =C4= C_4=C4​
  • acid part: ethanoic acid CH3COOHCH_3COOHCH3​COOH =C2= C_2=C2​

Thus the ester is: CH3COOC(CH3)3CH_3COO C(CH_3)_3CH3​COOC(CH3​)3​ which is tert-butyl acetate.

Check molecular formula:

  • Carbons: 2+4=62+4=62+4=6
  • Hydrogens: 121212
  • Oxygens: 222

So formula is indeed: C6H12O2C_6H_{12}O_2C6​H12​O2​


  1. Hydrolysis check

On hydrolysis: CH3COOC(CH3)3+H2O→H+CH3COOH+(CH3)3COHCH_3COOC(CH_3)_3 + H_2O \xrightarrow{H^+} CH_3COOH + (CH_3)_3COHCH3​COOC(CH3​)3​+H2​OH+​CH3​COOH+(CH3​)3​COH

Products are:

  • B=CH3COOHB = CH_3COOHB=CH3​COOH (carboxylic acid)
  • C=(CH3)3COHC = (CH_3)_3COHC=(CH3​)3​COH (tertiary alcohol)

This satisfies the Lucas test condition.


  1. Conclusion

Therefore, compound AAA is tert-butyl acetate.

Since the stored correct answer is D, the derived answer agrees provided option D corresponds to tert-butyl acetate.

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