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In the Fischer esterification reaction a carboxylic acid reacts with an excess of alcohol in acidic conditions to for...

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In the Fischer esterification reaction a carboxylic acid reacts with an excess of alcohol in acidic conditions to form an ester. During the reaction the sp2 hybridized carbonyl carbon of the acid forms an sp3 hybridized intermediate before returning to sp2 hybridization in the product. Draw the structure of the neutral sp3 hybridized intermediate and the ester product in the reaction between pentanioc acid and n-propanol.

Which reactant provides the oxygen atom found in the ester linkage: Pentanoic acid, or propanol?

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Concepts and reason

The Fischer esterification is an organic reaction used to condense a carboxylic acid and an alcohol in order to form an ester using an acid as catalyst. Thus, it is also called an acid-catalyzed esterification.

Fundamentals

Fischer esterification involves the reaction of carboxylic group with alcoholic group to form an ester along with dehydration in the presence of an acid catalyst.

The mechanism of the Fischer esterification reaction for pentanoic acid and n-propanol is given below:

но
н
CH,CH2CH2CH2
+ CH;CH2CH2ОН
CH,CH2CH2CH2
ОН
Но.
Н
ОН
н
ОН
0—СH,СH,CH,
6-CH2CH2CH
-н
CH,CH2CH2CH
ОН
CH,CH2CH2CH
ОН
н
О

The oxygen present in the ester linkage is provided by propanol.

Ans:

The structures of the sp
hybridized intermediate and the ester product are as follows:

ОН
0—CH,CH,СH,
CH2CH2CH2CH
-0—СН,СH,CH,
CH,CH2CH2CH
ОН

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