Describe and give examples of base-catalyzed nucleophilic addition reactions occurring at the carboxy1 carbon.

Short Answer

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Base-catalyzed nucleophilic addition reactions involve a nucleophile reacting with an electrophile in the presence of a base catalyst. In this case, the electrophile is the carboxyl carbon in a molecule. The carboxyl carbon is the carbon atom within the carboxyl functional group (COOH), which consists of a carbonyl group (C=O) bonded to a hydroxyl group (O-H). In the reaction mechanism, the base catalyst abstracts a proton from the hydroxyl group, and the nucleophile attacks the carboxyl carbon. This results in the addition of the nucleophile to the carboxyl carbon, forming a new molecule. Examples of such reactions include the reaction of acetic acid with an alkoxide ion (\( CH_3COOH + R'O^- \rightarrow CH_3COOR + OH^- \)) to form an ester, and the reaction of a carboxylic acid with ammonia (\[ RCOOH + NH_3 \rightarrow RCONH_2 + H_2O \]) to form an amide.

Step by step solution

01

Define base-catalyzed nucleophilic addition reactions

A base-catalyzed nucleophilic addition reaction is a type of reaction where a nucleophile, which is a species with a pair of electrons, reacts with an electrophile, which is a species deficient in electrons, in the presence of a base catalyst. In this case, the electrophile is the carboxyl carbon in a molecule.
02

Identify the carboxyl carbon

The carboxyl carbon is the carbon atom present in a carboxyl functional group, written as -COOH. This functional group consists of a carbonyl group (C=O) bonded to a hydroxyl group (O-H). The carboxyl carbon is the carbon atom that is double-bonded to the oxygen atom.
03

Explain the mechanism of the base-catalyzed nucleophilic addition reaction

In a base-catalyzed nucleophilic addition reaction, the base catalyst first abstracts a proton from the hydroxyl group of the carboxyl functional group, forming a carboxylate anion. The nucleophile then attacks the carboxyl carbon, forming a new bond with it. The double bond between the carboxyl carbon and the oxygen atom is broken, with the electrons becoming a part of the new bond formed with the nucleophile. This ultimately results in the addition of the nucleophile to the carboxyl carbon and the formation of a new molecule.
04

Provide examples of base-catalyzed nucleophilic addition reactions

Some examples of base-catalyzed nucleophilic addition reactions include: 1. Reaction of Acetic acid with an alkoxide ion: \( CH_3COOH + R'O^- \rightarrow CH_3COOR + OH^- \) In this case, the alkoxide ion \( (R'O^-) \) acts as a nucleophile, attacking the carbonyl carbon in the acetic acid molecule. The base catalyst abstracts a proton from the hydroxyl group of the carboxyl group, forming an acetate ion. The final product is an ester. 2. Reaction of a carboxylic acid with ammonia: \[ RCOOH + NH_3 \rightarrow RCONH_2 + H_2O \] In this reaction, ammonia \( NH_3 \) acts as a nucleophile and attacks the carbonyl carbon in the carboxylic acid (RCOOH) molecule. The base catalyst abstracts a proton from the hydroxyl group of the carboxyl group, forming a carboxylate ion. The final product is an amide.

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