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Fischer esterification of mesitoic acid (2, 4, 6-trimethylbenzoic acid) is extremely slow compared with benzoic acid itself. What is the major factor accounting for this difference in reactivity?
- a)Steric hindrance by the ortho methyl groups
- b)The electron donating inductive effect of methyl substituents
- c)Acid-catalysed rearrangement of the methyl substituents
- d)Rapid acid-catalysed decarboxylation of mesitoic acid
Correct answer is option 'A'. Can you explain this answer?
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Fischer esterification of mesitoic acid (2, 4, 6-trimethylbenzoic acid...
The two ortho methyl group makes —COOH highly sterically hinderded for attack of ROH. Most Upvoted Answer
Fischer esterification of mesitoic acid (2, 4, 6-trimethylbenzoic acid...
Steric hindrance by the ortho methyl groups
The major factor accounting for the slow reactivity of mesitoic acid (2, 4, 6-trimethylbenzoic acid) in Fischer esterification compared to benzoic acid itself is steric hindrance caused by the ortho methyl groups.
Steric hindrance:
Steric hindrance refers to the interference in the reaction caused by the bulkiness of substituents near the reaction site. In the case of mesitoic acid, there are three methyl groups attached to the benzene ring in the ortho positions. These methyl groups create steric hindrance, which restricts the approach of the alcohol and the acid catalyst to the reaction site.
Effect on Fischer esterification:
In Fischer esterification, an alcohol reacts with a carboxylic acid in the presence of an acid catalyst to form an ester. The reaction involves the nucleophilic attack of the alcohol on the carbonyl group of the carboxylic acid, followed by elimination of water.
The steric hindrance caused by the ortho methyl groups in mesitoic acid restricts the approach of the alcohol molecule to the carbonyl carbon of the acid. This hindrance makes it difficult for the alcohol to effectively attack the carbonyl group and form the intermediate necessary for ester formation.
As a result, the reaction rate of Fischer esterification is significantly slower for mesitoic acid compared to benzoic acid, which does not have any ortho substituents. The absence of bulky groups in benzoic acid allows for easier access of the alcohol and acid catalyst to the reaction site, leading to a faster reaction rate.
Conclusion:
Overall, the steric hindrance caused by the ortho methyl groups in mesitoic acid is the major factor accounting for the difference in reactivity between mesitoic acid and benzoic acid in Fischer esterification. The bulkiness of the substituents hinders the approach of the alcohol and acid catalyst to the reaction site, resulting in a slower reaction rate.
The major factor accounting for the slow reactivity of mesitoic acid (2, 4, 6-trimethylbenzoic acid) in Fischer esterification compared to benzoic acid itself is steric hindrance caused by the ortho methyl groups.
Steric hindrance:
Steric hindrance refers to the interference in the reaction caused by the bulkiness of substituents near the reaction site. In the case of mesitoic acid, there are three methyl groups attached to the benzene ring in the ortho positions. These methyl groups create steric hindrance, which restricts the approach of the alcohol and the acid catalyst to the reaction site.
Effect on Fischer esterification:
In Fischer esterification, an alcohol reacts with a carboxylic acid in the presence of an acid catalyst to form an ester. The reaction involves the nucleophilic attack of the alcohol on the carbonyl group of the carboxylic acid, followed by elimination of water.
The steric hindrance caused by the ortho methyl groups in mesitoic acid restricts the approach of the alcohol molecule to the carbonyl carbon of the acid. This hindrance makes it difficult for the alcohol to effectively attack the carbonyl group and form the intermediate necessary for ester formation.
As a result, the reaction rate of Fischer esterification is significantly slower for mesitoic acid compared to benzoic acid, which does not have any ortho substituents. The absence of bulky groups in benzoic acid allows for easier access of the alcohol and acid catalyst to the reaction site, leading to a faster reaction rate.
Conclusion:
Overall, the steric hindrance caused by the ortho methyl groups in mesitoic acid is the major factor accounting for the difference in reactivity between mesitoic acid and benzoic acid in Fischer esterification. The bulkiness of the substituents hinders the approach of the alcohol and acid catalyst to the reaction site, resulting in a slower reaction rate.
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Fischer esterification of mesitoic acid (2, 4, 6-trimethylbenzoic acid) is extremely slow compared with benzoic acid itself. What is the major factor accounting for this difference in reactivity?a)Steric hindrance by the ortho methyl groupsb)The electron donating inductive effect of methyl substituentsc)Acid-catalysed rearrangement of the methyl substituentsd)Rapid acid-catalysed decarboxylation of mesitoic acidCorrect answer is option 'A'. Can you explain this answer?
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Fischer esterification of mesitoic acid (2, 4, 6-trimethylbenzoic acid) is extremely slow compared with benzoic acid itself. What is the major factor accounting for this difference in reactivity?a)Steric hindrance by the ortho methyl groupsb)The electron donating inductive effect of methyl substituentsc)Acid-catalysed rearrangement of the methyl substituentsd)Rapid acid-catalysed decarboxylation of mesitoic acidCorrect answer is option 'A'. 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 Fischer esterification of mesitoic acid (2, 4, 6-trimethylbenzoic acid) is extremely slow compared with benzoic acid itself. What is the major factor accounting for this difference in reactivity?a)Steric hindrance by the ortho methyl groupsb)The electron donating inductive effect of methyl substituentsc)Acid-catalysed rearrangement of the methyl substituentsd)Rapid acid-catalysed decarboxylation of mesitoic acidCorrect answer is option 'A'. Can you explain this answer? covers all topics & solutions for JEE 2024 Exam. Find important definitions, questions, meanings, examples, exercises and tests below for Fischer esterification of mesitoic acid (2, 4, 6-trimethylbenzoic acid) is extremely slow compared with benzoic acid itself. What is the major factor accounting for this difference in reactivity?a)Steric hindrance by the ortho methyl groupsb)The electron donating inductive effect of methyl substituentsc)Acid-catalysed rearrangement of the methyl substituentsd)Rapid acid-catalysed decarboxylation of mesitoic acidCorrect answer is option 'A'. Can you explain this answer?.
Fischer esterification of mesitoic acid (2, 4, 6-trimethylbenzoic acid) is extremely slow compared with benzoic acid itself. What is the major factor accounting for this difference in reactivity?a)Steric hindrance by the ortho methyl groupsb)The electron donating inductive effect of methyl substituentsc)Acid-catalysed rearrangement of the methyl substituentsd)Rapid acid-catalysed decarboxylation of mesitoic acidCorrect answer is option 'A'. 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 Fischer esterification of mesitoic acid (2, 4, 6-trimethylbenzoic acid) is extremely slow compared with benzoic acid itself. What is the major factor accounting for this difference in reactivity?a)Steric hindrance by the ortho methyl groupsb)The electron donating inductive effect of methyl substituentsc)Acid-catalysed rearrangement of the methyl substituentsd)Rapid acid-catalysed decarboxylation of mesitoic acidCorrect answer is option 'A'. Can you explain this answer? covers all topics & solutions for JEE 2024 Exam. Find important definitions, questions, meanings, examples, exercises and tests below for Fischer esterification of mesitoic acid (2, 4, 6-trimethylbenzoic acid) is extremely slow compared with benzoic acid itself. What is the major factor accounting for this difference in reactivity?a)Steric hindrance by the ortho methyl groupsb)The electron donating inductive effect of methyl substituentsc)Acid-catalysed rearrangement of the methyl substituentsd)Rapid acid-catalysed decarboxylation of mesitoic acidCorrect answer is option 'A'. Can you explain this answer?.
Solutions for Fischer esterification of mesitoic acid (2, 4, 6-trimethylbenzoic acid) is extremely slow compared with benzoic acid itself. What is the major factor accounting for this difference in reactivity?a)Steric hindrance by the ortho methyl groupsb)The electron donating inductive effect of methyl substituentsc)Acid-catalysed rearrangement of the methyl substituentsd)Rapid acid-catalysed decarboxylation of mesitoic acidCorrect answer is option 'A'. Can you explain this answer? in English & in Hindi are available as part of our courses for JEE.
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Fischer esterification of mesitoic acid (2, 4, 6-trimethylbenzoic acid) is extremely slow compared with benzoic acid itself. What is the major factor accounting for this difference in reactivity?a)Steric hindrance by the ortho methyl groupsb)The electron donating inductive effect of methyl substituentsc)Acid-catalysed rearrangement of the methyl substituentsd)Rapid acid-catalysed decarboxylation of mesitoic acidCorrect answer is option 'A'. Can you explain this answer?, a detailed solution for Fischer esterification of mesitoic acid (2, 4, 6-trimethylbenzoic acid) is extremely slow compared with benzoic acid itself. What is the major factor accounting for this difference in reactivity?a)Steric hindrance by the ortho methyl groupsb)The electron donating inductive effect of methyl substituentsc)Acid-catalysed rearrangement of the methyl substituentsd)Rapid acid-catalysed decarboxylation of mesitoic acidCorrect answer is option 'A'. Can you explain this answer? has been provided alongside types of Fischer esterification of mesitoic acid (2, 4, 6-trimethylbenzoic acid) is extremely slow compared with benzoic acid itself. What is the major factor accounting for this difference in reactivity?a)Steric hindrance by the ortho methyl groupsb)The electron donating inductive effect of methyl substituentsc)Acid-catalysed rearrangement of the methyl substituentsd)Rapid acid-catalysed decarboxylation of mesitoic acidCorrect answer is option 'A'. Can you explain this answer? theory, EduRev gives you an
ample number of questions to practice Fischer esterification of mesitoic acid (2, 4, 6-trimethylbenzoic acid) is extremely slow compared with benzoic acid itself. What is the major factor accounting for this difference in reactivity?a)Steric hindrance by the ortho methyl groupsb)The electron donating inductive effect of methyl substituentsc)Acid-catalysed rearrangement of the methyl substituentsd)Rapid acid-catalysed decarboxylation of mesitoic acidCorrect answer is option 'A'. Can you explain this answer? tests, examples and also practice JEE tests.
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