Textbook Question
Show how each of the following esters could be prepared using a carboxylic acid as one of the starting materials:
a. methyl butyrate (odor of apples)
22. Carboxylic Acid Derivatives: NAS
Fischer Esterification
3:13 minutesProblem 44d,e
Textbook Question
Predict the esterification products of the following acid/alcohol pairs.
(d) 
(e) 
Verified step by step guidance1
Step 1: Esterification is a reaction between a carboxylic acid and an alcohol, typically in the presence of an acid catalyst, to form an ester and water. Analyze the given pairs of acid and alcohol.
Step 2: For the first pair (benzoic acid and ethanol), identify the functional groups involved. Benzoic acid contains a carboxylic acid group (-COOH), and ethanol contains a hydroxyl group (-OH). The reaction will involve the nucleophilic attack of the alcohol's oxygen on the carbonyl carbon of the acid.
Step 3: Write the general reaction for esterification: \( \text{R-COOH} + \text{R'-OH} \rightarrow \text{R-COOR'} + \text{H}_2\text{O} \). In this case, the product will be ethyl benzoate (an ester) and water.
Step 4: For the second pair (phenol and acetic acid), note that phenol is an aromatic alcohol, and acetic acid is a carboxylic acid. Phenols are less reactive in esterification compared to aliphatic alcohols, but under acidic conditions, the reaction can proceed to form phenyl acetate (an ester) and water.
Step 5: Summarize the products: The first reaction yields ethyl benzoate, and the second reaction yields phenyl acetate. Ensure proper reaction conditions, such as the presence of an acid catalyst (e.g., sulfuric acid), to facilitate the esterification process.
Verified video answer for a similar problem:This video solution was recommended by our tutors as helpful for the problem above
Video duration:
3mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Esterification Reaction
Esterification is a chemical reaction between an alcohol and a carboxylic acid, resulting in the formation of an ester and water. This reaction typically occurs under acidic conditions and involves the nucleophilic attack of the alcohol's hydroxyl group on the carbonyl carbon of the acid, leading to the elimination of a water molecule.
Recommended video:
1:21
Reactions of Amino Acids: Esterification Concept 1
Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In esterification, the carboxylic acid (with the -COOH group) and the alcohol (with the -OH group) are the key functional groups that interact to form the ester product.
Recommended video:
Guided course
02:36Identifying Functional Groups
Reaction Mechanism
The reaction mechanism of esterification involves several steps, including protonation of the carbonyl oxygen, nucleophilic attack by the alcohol, and subsequent elimination of water. Understanding this mechanism is crucial for predicting the products of the reaction, as it helps identify the structure of the ester formed from the specific acid and alcohol used.
Recommended video:
Guided course
02:16Heck Reaction Mechanism
Related Videos
Related Practice