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Propose mechanisms for the following reactions. Does this
Chapter 15, Problem 49SP(choose chapter or problem)
Propose mechanisms for the following reactions.
Does this reaction proceed with retention, inversion, or racemization of the asymmetric carbon atom?
Questions & Answers
QUESTION:
Propose mechanisms for the following reactions.
Does this reaction proceed with retention, inversion, or racemization of the asymmetric carbon atom?
ANSWER:Solution 49SP
(a)
Acid chloride reacts with alcohol to from an ester. The reaction is shown below:
The mechanism of the reaction is shown below:
In step-I, alcohol acts as a nucleophile which attacks on the electrophilic carbonyl carbon to form tetrahedral intermediate.
In step-II, chlorine leaves with a pair of electrons to form protonated ester.
In the final step, deprotonation to form target product.
(b)
Esters undergo base promoted hydrolysis in presence of NaOH and water to form carboxylate ion and alcohol.
The mechanism of the reaction is shown below:
In step-1, hydroxide ion acts as a nucleophile which attacks on the electrophilic carbonyl carbon to form alkoxide ion.
In step-2, ethoxide ion leaves with pair of electrons to form benzoic acid and ethoxide ion.
In final step, ethoxide ion is strong base which abstracts a proton from benzoic acid to form benzoate and methanol.
(c)
Esters undergo acid catalyzed hydrolysis in presence of and water to form carboxylic acid and alcohol.
The mechanism of the reaction is shown below:
In step-I, carbonyl oxygen abstracts proton from acid to form protonated ester.
