Textbook Question
Using the pKa values listed in [TABLE 15.1], predict the products of the following reactions:
c.
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22. Carboxylic Acid Derivatives: NAS
Nucleophilic Acyl Substitution
5:47 minutesProblem 12e
Textbook Question
Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?
e. 
Verified step by step guidance1
Step 1: Identify the functional group in the target compound. The compound contains an ester functional group, specifically ethyl pentyl ester.
Step 2: Recognize that acetyl chloride (CH3COCl) is an acyl chloride, which is reactive and can be converted into an ester through nucleophilic acyl substitution.
Step 3: Determine the neutral nucleophile required to form the ester. To synthesize the target compound, the nucleophile must be cyclopentanol (C5H9OH), as it provides the cyclopentyl group in the ester.
Step 4: Outline the reaction mechanism. Acetyl chloride reacts with cyclopentanol in the presence of a base (such as pyridine) to neutralize the HCl byproduct. The nucleophilic oxygen of cyclopentanol attacks the carbonyl carbon of acetyl chloride, forming the ester bond.
Step 5: Ensure proper reaction conditions. The reaction should be carried out under anhydrous conditions to prevent hydrolysis of acetyl chloride, and a base like pyridine is used to absorb the HCl formed during the reaction.
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Video duration:
5mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Acyl Substitution
Nucleophilic acyl substitution is a fundamental reaction in organic chemistry where a nucleophile attacks the carbonyl carbon of an acyl compound, such as an acid chloride, leading to the replacement of a leaving group (like chloride) with the nucleophile. This reaction is crucial for synthesizing various organic compounds, including esters and amides.
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Acetyl Chloride
Acetyl chloride is an acyl chloride derived from acetic acid, characterized by the presence of a carbonyl group (C=O) and a chlorine atom. It is a reactive electrophile commonly used in organic synthesis to introduce acetyl groups into nucleophiles, facilitating the formation of esters and other derivatives through nucleophilic acyl substitution.
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Neutral Nucleophiles
Neutral nucleophiles are species that possess a lone pair of electrons and can donate them to electrophiles without carrying a formal charge. Examples include alcohols, amines, and water. In the context of nucleophilic acyl substitution, a neutral nucleophile can effectively attack the carbonyl carbon of acetyl chloride, leading to the formation of a new compound.
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