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Mobile App Chapter 18: Problem 17
Predict the organic products obtained from the acid-induced hydrolysis of N-phenylpentanamide.
Short Answer
Expert verified
Pentanoic acid \ (C_5H_{10}O_2\) and aniline \ (C_6H_5NH_2\) are the products.
Step by step solution
01
Identify the Functional Groups
Examine the structure of N-phenylpentanamide. It contains an amide functional group \( C(O)NH\) attached to a phenyl ring and a pentyl chain.
02
Understand the Reaction Mechanism
Acid-induced hydrolysis of amides generally follows the mechanism where the amide bond is broken down into a carboxylic acid and an amine. The reaction proceeds through protonation of the amide, making it more susceptible to nucleophilic attack by water.
03
Protonation of the Amide Nitrogen
In acidic conditions, the nitrogen of the amide group is protonated, forming \( C(O)NH_2^+ \).
04
Nucleophilic Attack by Water
The protonated amide then reacts with water, leading to the formation of a tetrahedral intermediate that eventually breaks down to form a carboxylic acid and an ammonium ion.
05
Formation of Products
After the breakdown of the tetrahedral intermediate, the end products are a carboxylic acid (pentanoic acid) and an aromatic amine (aniline).
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Amide Functional Group
An amide functional group is a distinct component found in organic chemistry. It consists of a carbonyl group (C=O) bonded to a nitrogen atom (N). In the case of N-phenylpentanamide, this functional group links a phenyl ring to a pentyl chain. Amides are known for their stability, but under certain conditions, like the presence of acid, they can be hydrolyzed. This hydrolysis process involves breaking down the amide bond into simpler molecules such as carboxylic acids and amines.
Reaction Mechanism
The mechanism of acid-induced hydrolysis involves several steps that lead to the breakdown of the amide bond. Typically, it follows these stages:
- First, the amide is protonated, increasing its susceptibility to further reactions.
- Next, water acts as a nucleophile and attacks the protonated amide.
- This leads to the formation of a tetrahedral intermediate, which eventually breaks down to yield the final products: a carboxylic acid and an amine.
Protonation
Protonation is the initial step in the acid-induced hydrolysis of amides. Here, the nitrogen atom in the amide group accepts a proton (H⁺) from the acidic environment. This forms a protonated amide, making it more reactive. Protonation enhances the electrophilicity of the carbonyl carbon, making it more prone to attacks by nucleophiles such as water. Hence, protonation is crucial for decreasing the stability of the amide, aiding in its subsequent breakdown.
Nucleophilic Attack
After protonation, the next significant step is the nucleophilic attack. In this context, water serves as the nucleophile. A nucleophile is a species that donates an electron pair to form a chemical bond. Water, being rich in electron pairs, attacks the electrophilic carbonyl carbon of the protonated amide. This attack is what initiates the formation of the tetrahedral intermediate, an essential part of the reaction process. The effectiveness of this nucleophilic attack is facilitated by the prior protonation of the amide, which makes the carbonyl carbon more accessible to nucleophiles.
Tetrahedral Intermediate
The nucleophilic attack of water on the protonated amide forms a temporary structure known as the tetrahedral intermediate. This intermediate is characterized by a central carbon atom bonded to four different atoms or groups (hence the name 'tetrahedral'). In this case, the carbon is connected to the original nitrogen, an incoming hydroxyl group (from water), and two remaining substituents. The tetrahedral intermediate is unstable and soon collapses. This collapse leads to the breaking of the C-N bond and the formation of the final products: pentanoic acid and an ammonium ion, which subsequently becomes aniline after losing a proton.
