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2, 2-dimethyl-1 , 3-cyclohexanedione is refluxed several hours in an aqueous dioxane solution of sodium hydroxide (10%). The resulting solution is adjusted to pH = 5 by the addition of dilute HCl and then extracted with ether. What compound has been prepared by this procedure?
- a)2-cyclohexenone
- b)5-oxohexanoic acid
- c)6-methylheptanoic acid
- d)5-oxo-6-methylheptanoic acid
Correct answer is option 'D'. Can you explain this answer?
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Procedure:
1. Reflux 2,2-dimethyl-1,3-cyclohexanedione in an aqueous dioxane solution of sodium hydroxide (10%).
2. Adjust the resulting solution to pH = 5 by the addition of dilute HCl.
3. Extract the solution with ether.
Explanation:
The given compound, 2,2-dimethyl-1,3-cyclohexanedione, undergoes a series of reactions when subjected to the described procedure, leading to the formation of 5-oxo-6-methylheptanoic acid.
Step 1: Reflux in aqueous dioxane solution of sodium hydroxide (10%):
When the compound is refluxed in an aqueous dioxane solution of sodium hydroxide, it undergoes a base-catalyzed aldol condensation reaction.
The enol form of the compound (2,2-dimethyl-1,3-cyclohexanedione) reacts with itself to form a cyclic intermediate via an aldol condensation reaction. This cyclic intermediate then undergoes keto-enol tautomerism to form the final product.
Step 2: Adjustment to pH = 5:
The resulting solution is then adjusted to pH = 5 by the addition of dilute hydrochloric acid (HCl). This acidic condition helps in the extraction of the desired product.
Step 3: Extraction with ether:
The solution is extracted with ether to separate and isolate the desired product, 5-oxo-6-methylheptanoic acid, from the aqueous solution.
Conclusion:
By subjecting 2,2-dimethyl-1,3-cyclohexanedione to reflux in an aqueous dioxane solution of sodium hydroxide, adjusting the resulting solution to pH = 5, and extracting with ether, the compound 5-oxo-6-methylheptanoic acid is obtained.
1. Reflux 2,2-dimethyl-1,3-cyclohexanedione in an aqueous dioxane solution of sodium hydroxide (10%).
2. Adjust the resulting solution to pH = 5 by the addition of dilute HCl.
3. Extract the solution with ether.
Explanation:
The given compound, 2,2-dimethyl-1,3-cyclohexanedione, undergoes a series of reactions when subjected to the described procedure, leading to the formation of 5-oxo-6-methylheptanoic acid.
Step 1: Reflux in aqueous dioxane solution of sodium hydroxide (10%):
When the compound is refluxed in an aqueous dioxane solution of sodium hydroxide, it undergoes a base-catalyzed aldol condensation reaction.
The enol form of the compound (2,2-dimethyl-1,3-cyclohexanedione) reacts with itself to form a cyclic intermediate via an aldol condensation reaction. This cyclic intermediate then undergoes keto-enol tautomerism to form the final product.
Step 2: Adjustment to pH = 5:
The resulting solution is then adjusted to pH = 5 by the addition of dilute hydrochloric acid (HCl). This acidic condition helps in the extraction of the desired product.
Step 3: Extraction with ether:
The solution is extracted with ether to separate and isolate the desired product, 5-oxo-6-methylheptanoic acid, from the aqueous solution.
Conclusion:
By subjecting 2,2-dimethyl-1,3-cyclohexanedione to reflux in an aqueous dioxane solution of sodium hydroxide, adjusting the resulting solution to pH = 5, and extracting with ether, the compound 5-oxo-6-methylheptanoic acid is obtained.
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2, 2-dimethyl-1 , 3-cyclohexanedione is refluxed several hours in an aqueous dioxane solution of sodium hydroxide (10%). The resulting solution is adjusted to pH = 5 by the addition of dilute HCl and then extracted with ether. What compound has been prepared by this procedure?a)2-cyclohexenoneb)5-oxohexanoic acidc)6-methylheptanoic acidd)5-oxo-6-methylheptanoic acidCorrect answer is option 'D'. Can you explain this answer?
Question Description
2, 2-dimethyl-1 , 3-cyclohexanedione is refluxed several hours in an aqueous dioxane solution of sodium hydroxide (10%). The resulting solution is adjusted to pH = 5 by the addition of dilute HCl and then extracted with ether. What compound has been prepared by this procedure?a)2-cyclohexenoneb)5-oxohexanoic acidc)6-methylheptanoic acidd)5-oxo-6-methylheptanoic acidCorrect answer is option 'D'. Can you explain this answer? for JEE 2024 is part of JEE preparation. The Question and answers have been prepared according to the JEE exam syllabus. Information about 2, 2-dimethyl-1 , 3-cyclohexanedione is refluxed several hours in an aqueous dioxane solution of sodium hydroxide (10%). The resulting solution is adjusted to pH = 5 by the addition of dilute HCl and then extracted with ether. What compound has been prepared by this procedure?a)2-cyclohexenoneb)5-oxohexanoic acidc)6-methylheptanoic acidd)5-oxo-6-methylheptanoic acidCorrect answer is option 'D'. Can you explain this answer? covers all topics & solutions for JEE 2024 Exam. Find important definitions, questions, meanings, examples, exercises and tests below for 2, 2-dimethyl-1 , 3-cyclohexanedione is refluxed several hours in an aqueous dioxane solution of sodium hydroxide (10%). The resulting solution is adjusted to pH = 5 by the addition of dilute HCl and then extracted with ether. What compound has been prepared by this procedure?a)2-cyclohexenoneb)5-oxohexanoic acidc)6-methylheptanoic acidd)5-oxo-6-methylheptanoic acidCorrect answer is option 'D'. Can you explain this answer?.
2, 2-dimethyl-1 , 3-cyclohexanedione is refluxed several hours in an aqueous dioxane solution of sodium hydroxide (10%). The resulting solution is adjusted to pH = 5 by the addition of dilute HCl and then extracted with ether. What compound has been prepared by this procedure?a)2-cyclohexenoneb)5-oxohexanoic acidc)6-methylheptanoic acidd)5-oxo-6-methylheptanoic acidCorrect answer is option 'D'. Can you explain this answer? for JEE 2024 is part of JEE preparation. The Question and answers have been prepared according to the JEE exam syllabus. Information about 2, 2-dimethyl-1 , 3-cyclohexanedione is refluxed several hours in an aqueous dioxane solution of sodium hydroxide (10%). The resulting solution is adjusted to pH = 5 by the addition of dilute HCl and then extracted with ether. What compound has been prepared by this procedure?a)2-cyclohexenoneb)5-oxohexanoic acidc)6-methylheptanoic acidd)5-oxo-6-methylheptanoic acidCorrect answer is option 'D'. Can you explain this answer? covers all topics & solutions for JEE 2024 Exam. Find important definitions, questions, meanings, examples, exercises and tests below for 2, 2-dimethyl-1 , 3-cyclohexanedione is refluxed several hours in an aqueous dioxane solution of sodium hydroxide (10%). The resulting solution is adjusted to pH = 5 by the addition of dilute HCl and then extracted with ether. What compound has been prepared by this procedure?a)2-cyclohexenoneb)5-oxohexanoic acidc)6-methylheptanoic acidd)5-oxo-6-methylheptanoic acidCorrect answer is option 'D'. Can you explain this answer?.
Solutions for 2, 2-dimethyl-1 , 3-cyclohexanedione is refluxed several hours in an aqueous dioxane solution of sodium hydroxide (10%). The resulting solution is adjusted to pH = 5 by the addition of dilute HCl and then extracted with ether. What compound has been prepared by this procedure?a)2-cyclohexenoneb)5-oxohexanoic acidc)6-methylheptanoic acidd)5-oxo-6-methylheptanoic acidCorrect answer is option 'D'. Can you explain this answer? in English & in Hindi are available as part of our courses for JEE.
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