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Which of the following represents the best method for converting a carboxylic acid to an aldehyde?
- a)Convert the acid to an acid chloride, and react the acid chloride with water.
- b)Reduce the acid with LiAlH4.
- c)Convert the acid to an acid chloride, and reduce the acid chloride with lithium aluminium tri(t-butoxy) hydride.
- d)Convert the acid to an acid chloride, react the acid chloride with a Grignard reagent, and reduce the product with LiAlH4.
Correct answer is option 'C'. Can you explain this answer?
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Which of the following represents the best method for converting a ca...
The best method for converting a carboxylic acid to an aldehyde is option 'C', which involves converting the acid to an acid chloride and reducing the acid chloride with lithium aluminium tri(t-butoxy) hydride.
Explanation:
Step 1: Conversion of carboxylic acid to acid chloride
The carboxylic acid is first converted to an acid chloride. This can be achieved by reacting the carboxylic acid with thionyl chloride (SOCl2) or oxalyl chloride (COCl)2. The reaction proceeds via the formation of an intermediate acyl chloride, which is more reactive than the carboxylic acid.
Step 2: Reduction of acid chloride with lithium aluminium tri(t-butoxy) hydride
The acid chloride is then reduced to an aldehyde using lithium aluminium tri(t-butoxy) hydride (LiAlH[OC(CH3)3]3). This reagent is a mild reducing agent that selectively reduces the acid chloride to an aldehyde without further reduction to an alcohol.
The reduction proceeds via the following steps:
- The LiAlH[OC(CH3)3]3 reagent donates a hydride ion (H-) to the electrophilic carbon of the acid chloride, resulting in the formation of an aldehyde.
- The t-butoxy group (OC(CH3)3) of the reagent serves as a leaving group, which is displaced by the hydride ion.
- The resulting aldehyde is then isolated as the final product.
Advantages of option 'C':
- Option 'C' offers a selective and mild method for converting carboxylic acids to aldehydes.
- The use of lithium aluminium tri(t-butoxy) hydride as the reducing agent prevents further reduction to alcohols.
- The reaction conditions are relatively mild, allowing for the preservation of sensitive functional groups.
Other options:
- Option 'A' involves converting the acid to an acid chloride and reacting the acid chloride with water. This would result in the hydrolysis of the acid chloride to the corresponding carboxylic acid, rather than the desired aldehyde.
- Option 'B' involves reducing the acid directly with LiAlH4, which would result in the formation of the corresponding primary alcohol, rather than the desired aldehyde.
- Option 'D' involves converting the acid to an acid chloride, reacting the acid chloride with a Grignard reagent, and reducing the product with LiAlH4. This method would result in the formation of a tertiary alcohol, rather than the desired aldehyde.
Therefore, option 'C' is the most appropriate method for converting a carboxylic acid to an aldehyde.
Explanation:
Step 1: Conversion of carboxylic acid to acid chloride
The carboxylic acid is first converted to an acid chloride. This can be achieved by reacting the carboxylic acid with thionyl chloride (SOCl2) or oxalyl chloride (COCl)2. The reaction proceeds via the formation of an intermediate acyl chloride, which is more reactive than the carboxylic acid.
Step 2: Reduction of acid chloride with lithium aluminium tri(t-butoxy) hydride
The acid chloride is then reduced to an aldehyde using lithium aluminium tri(t-butoxy) hydride (LiAlH[OC(CH3)3]3). This reagent is a mild reducing agent that selectively reduces the acid chloride to an aldehyde without further reduction to an alcohol.
The reduction proceeds via the following steps:
- The LiAlH[OC(CH3)3]3 reagent donates a hydride ion (H-) to the electrophilic carbon of the acid chloride, resulting in the formation of an aldehyde.
- The t-butoxy group (OC(CH3)3) of the reagent serves as a leaving group, which is displaced by the hydride ion.
- The resulting aldehyde is then isolated as the final product.
Advantages of option 'C':
- Option 'C' offers a selective and mild method for converting carboxylic acids to aldehydes.
- The use of lithium aluminium tri(t-butoxy) hydride as the reducing agent prevents further reduction to alcohols.
- The reaction conditions are relatively mild, allowing for the preservation of sensitive functional groups.
Other options:
- Option 'A' involves converting the acid to an acid chloride and reacting the acid chloride with water. This would result in the hydrolysis of the acid chloride to the corresponding carboxylic acid, rather than the desired aldehyde.
- Option 'B' involves reducing the acid directly with LiAlH4, which would result in the formation of the corresponding primary alcohol, rather than the desired aldehyde.
- Option 'D' involves converting the acid to an acid chloride, reacting the acid chloride with a Grignard reagent, and reducing the product with LiAlH4. This method would result in the formation of a tertiary alcohol, rather than the desired aldehyde.
Therefore, option 'C' is the most appropriate method for converting a carboxylic acid to an aldehyde.
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Community Answer
Which of the following represents the best method for converting a ca...
(i) This method will not work
Aldehyde will not form
(ii) Carboxylic acid are not reduced by LiAlH4.
(iii) This method is best
(iv) This method will produce alcohol rather than aldehyde:
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Which of the following represents the best method for converting a carboxylic acid to an aldehyde?a)Convert the acid to an acid chloride, and react the acid chloride with water.b)Reduce the acid with LiAlH4.c)Convert the acid to an acid chloride, and reduce the acid chloride with lithium aluminium tri(t-butoxy) hydride.d)Convert the acid to an acid chloride, react the acid chloride with a Grignard reagent, and reduce the product with LiAlH4.Correct answer is option 'C'. Can you explain this answer?
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Which of the following represents the best method for converting a carboxylic acid to an aldehyde?a)Convert the acid to an acid chloride, and react the acid chloride with water.b)Reduce the acid with LiAlH4.c)Convert the acid to an acid chloride, and reduce the acid chloride with lithium aluminium tri(t-butoxy) hydride.d)Convert the acid to an acid chloride, react the acid chloride with a Grignard reagent, and reduce the product with LiAlH4.Correct answer is option 'C'. 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 Which of the following represents the best method for converting a carboxylic acid to an aldehyde?a)Convert the acid to an acid chloride, and react the acid chloride with water.b)Reduce the acid with LiAlH4.c)Convert the acid to an acid chloride, and reduce the acid chloride with lithium aluminium tri(t-butoxy) hydride.d)Convert the acid to an acid chloride, react the acid chloride with a Grignard reagent, and reduce the product with LiAlH4.Correct answer is option 'C'. Can you explain this answer? covers all topics & solutions for JEE 2024 Exam. Find important definitions, questions, meanings, examples, exercises and tests below for Which of the following represents the best method for converting a carboxylic acid to an aldehyde?a)Convert the acid to an acid chloride, and react the acid chloride with water.b)Reduce the acid with LiAlH4.c)Convert the acid to an acid chloride, and reduce the acid chloride with lithium aluminium tri(t-butoxy) hydride.d)Convert the acid to an acid chloride, react the acid chloride with a Grignard reagent, and reduce the product with LiAlH4.Correct answer is option 'C'. Can you explain this answer?.
Which of the following represents the best method for converting a carboxylic acid to an aldehyde?a)Convert the acid to an acid chloride, and react the acid chloride with water.b)Reduce the acid with LiAlH4.c)Convert the acid to an acid chloride, and reduce the acid chloride with lithium aluminium tri(t-butoxy) hydride.d)Convert the acid to an acid chloride, react the acid chloride with a Grignard reagent, and reduce the product with LiAlH4.Correct answer is option 'C'. 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 Which of the following represents the best method for converting a carboxylic acid to an aldehyde?a)Convert the acid to an acid chloride, and react the acid chloride with water.b)Reduce the acid with LiAlH4.c)Convert the acid to an acid chloride, and reduce the acid chloride with lithium aluminium tri(t-butoxy) hydride.d)Convert the acid to an acid chloride, react the acid chloride with a Grignard reagent, and reduce the product with LiAlH4.Correct answer is option 'C'. Can you explain this answer? covers all topics & solutions for JEE 2024 Exam. Find important definitions, questions, meanings, examples, exercises and tests below for Which of the following represents the best method for converting a carboxylic acid to an aldehyde?a)Convert the acid to an acid chloride, and react the acid chloride with water.b)Reduce the acid with LiAlH4.c)Convert the acid to an acid chloride, and reduce the acid chloride with lithium aluminium tri(t-butoxy) hydride.d)Convert the acid to an acid chloride, react the acid chloride with a Grignard reagent, and reduce the product with LiAlH4.Correct answer is option 'C'. Can you explain this answer?.
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