Textbook Question
Using the pKa values listed in [TABLE 15.1], predict the products of the following reactions:
d.
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22. Carboxylic Acid Derivatives: NAS
Nucleophilic Acyl Substitution
4:21 minutesProblem 12f
Textbook Question
Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?
f. 
Verified step by step guidance1
Step 1: Analyze the target compound. The structure shows an ester functional group, specifically an ethyl ester, attached to a benzene ring substituted with two nitro groups and a methyl group.
Step 2: Identify the starting material, acetyl chloride (CH3COCl). Acetyl chloride is an acyl chloride, which is reactive and can undergo nucleophilic acyl substitution reactions to form esters.
Step 3: Determine the neutral nucleophile required to form the ester. To synthesize the target compound, the nucleophile must be a phenol derivative with the same substitution pattern as the benzene ring in the target compound: a methyl group and two nitro groups.
Step 4: Select the appropriate phenol derivative. The nucleophile should be 2-methyl-4,6-dinitrophenol, as it matches the substitution pattern of the benzene ring in the target compound.
Step 5: Outline the reaction mechanism. Acetyl chloride reacts with 2-methyl-4,6-dinitrophenol in the presence of a base (such as pyridine) to neutralize the HCl byproduct. This results in the formation of the ester bond, yielding the target compound.
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Video duration:
4mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In the context of acetyl chloride, the nucleophile must be neutral and capable of attacking the carbonyl carbon, leading to the formation of a new bond. Understanding this mechanism is crucial for predicting the products of reactions involving acetyl chloride.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
Acetyl Chloride Reactivity
Acetyl chloride is a reactive acyl chloride that can undergo nucleophilic acyl substitution due to the presence of the electron-withdrawing chlorine atom. This reactivity allows it to react with various nucleophiles, including alcohols and amines, to form esters and amides, respectively. Recognizing the reactivity of acetyl chloride helps in selecting appropriate nucleophiles for synthesizing desired compounds.
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Electrophilic Aromatic Substitution
Electrophilic aromatic substitution (EAS) is a reaction where an electrophile replaces a hydrogen atom on an aromatic ring. In the compound shown, the presence of nitro groups indicates that the aromatic ring is activated for further substitution. Understanding EAS is essential for predicting how the aromatic system will react with nucleophiles, especially when considering the influence of substituents on the ring's reactivity.
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