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Aldehydes Ketones and Carboxylic Acids question

2023 · 30 Jan · Shift 1 · Q5
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  5. /2023 · 30 Jan · Shift 1 · Q5

Aldehydes Ketones and Carboxylic Acids question

2023 · 30 Jan · Shift 1 · Q5

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
What is the correct order of acidity of the protons marked A−D\mathrm{A}-\mathrm{D}A−D in the given compounds ? JEE Main 2023 (Online) 30th January Morning Shift Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 78 English
  1. A
    HD>HC>HB>HA\mathrm{H}_{\mathrm{D}}\gt \mathrm{H}_{\mathrm{C}}\gt \mathrm{H}_{\mathrm{B}}\gt \mathrm{H}_{\mathrm{A}}HD​>HC​>HB​>HA​
  2. B
    HC>HA>HD>HB\mathrm{H}_{\mathrm{C}}\gt \mathrm{H}_{\mathrm{A}}\gt \mathrm{H}_{\mathrm{D}}\gt \mathrm{H}_{\mathrm{B}}HC​>HA​>HD​>HB​
  3. C
    HC>HD>HB>HA\mathrm{H}_{\mathrm{C}}\gt \mathrm{H}_{\mathrm{D}}\gt \mathrm{H}_{\mathrm{B}}\gt \mathrm{H}_{\mathrm{A}}HC​>HD​>HB​>HA​
  4. D
    HC>HD>HA>HB\mathrm{H}_{\mathrm{C}}\gt \mathrm{H}_{\mathrm{D}}\gt \mathrm{H}_{\mathrm{A}}\gt \mathrm{H}_{\mathrm{B}}HC​>HD​>HA​>HB​
View written solutionFree

Correct answer: D

  1. Idea used: acidity of a proton depends on the stability of the conjugate base formed after removing that proton.

  2. For the marked protons HA,HB,HC,HDH_A, H_B, H_C, H_DHA​,HB​,HC​,HD​, we compare how well the negative charge is stabilized after deprotonation.

  3. Most acidic proton: HCH_CHC​
    HCH_CHC​ is the proton whose removal gives an enolate/conjugate base stabilized most strongly by resonance with the carbonyl group and by the strongest electron-withdrawing environment. Hence it is the most acidic.

  4. Next: HDH_DHD​
    Removal of HDH_DHD​ also gives a resonance-stabilized conjugate base, but the stabilization is less than for HCH_CHC​. Therefore, HC>HDH_C > H_DHC​>HD​

  5. Compare HAH_AHA​ and HBH_BHB​
    Between these two, the conjugate base from HAH_AHA​ is more stabilized than that from HBH_BHB​ (due to better inductive/resonance support), so HA>HBH_A > H_BHA​>HB​

  6. Combining all comparisons, HC>HD>HA>HBH_C > H_D > H_A > H_BHC​>HD​>HA​>HB​

  7. Option matching: this corresponds to Option D.


Final answer: HC>HD>HA>HB\boxed{H_C > H_D > H_A > H_B}HC​>HD​>HA​>HB​​

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