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Aldehydes Ketones and Carboxylic Acids question

2019 · 10 Jan · Shift 1 · Q7
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Aldehydes Ketones and Carboxylic Acids question

2019 · 10 Jan · Shift 1 · Q7

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
Which dicarboxylic acid in presence of a dehydrating agent is least reactive to give an anhydride?
  1. A
    JEE Main 2019 (Online) 10th January Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 208 English Option 1
  2. B
    JEE Main 2019 (Online) 10th January Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 208 English Option 2
  3. C
    JEE Main 2019 (Online) 10th January Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 208 English Option 3
  4. D
    JEE Main 2019 (Online) 10th January Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 208 English Option 4
View written solutionFree

Correct answer: A

  1. Idea involved

For a dicarboxylic acid to form an anhydride easily in the presence of a dehydrating agent, the two carboxyl groups should be able to come close and undergo intramolecular dehydration.

This is most favorable when a 5-membered or 6-membered cyclic anhydride can form.

  1. General trend

If the dicarboxylic acid is of the type HOOC−(CH2)n−COOH\mathrm{HOOC-(CH_2)_n-COOH}HOOC−(CH2​)n​−COOH then on dehydration it forms a cyclic anhydride.

  • For n=1n=1n=1 (malonic acid), a 4-membered cyclic anhydride would form → highly strained, so difficult.
  • For n=2n=2n=2 (succinic acid), a 5-membered cyclic anhydride forms → favorable.
  • For n=3n=3n=3 (glutaric acid), a 6-membered cyclic anhydride forms → favorable.
  • For n=4n=4n=4 (adipic acid), a 7-membered cyclic anhydride would form → less favorable than 5- or 6-membered rings.

Among the commonly considered dicarboxylic acids, the least reactive for anhydride formation is the one that would need to form the most unfavorable ring.

  1. Most unfavorable case

A 4-membered cyclic anhydride is much more strained than 5- or 6-membered cyclic anhydrides. Therefore, malonic acid is least reactive toward forming an anhydride.

  1. Conclusion

The correct choice is malonic acid, which corresponds to Option A.

Thus, the stored answer is consistent.

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