Ch.11 - Reactions of Alcohols

Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook

Wade 9th Edition

Ch.11 - Reactions of Alcohols

Problem 44d,e

Chapter 11, Problem 44d,e

Predict the esterification products of the following acid/alcohol pairs.
(d)
(e)

Verified step by step guidance

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.

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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.

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.

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.

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Related Practice

Textbook Question

Show how you would make each compound, beginning with an alcohol of your choice.

(d)

(e)

(f)

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Textbook Question

Show how you would convert (S)-hexan-2-ol to

(a) (S)-2-chlorohexane.

(b) (R)-2-bromohexane.

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Textbook Question

Both cis- and trans-2-methylcyclohexanol undergo dehydration in warm sulfuric acid to give 1-methylcyclohexene as the major alkene product. These alcohols can also be converted to alkenes by tosylation using TsCl and pyridine, followed by elimination using KOC(CH₃)₃ as a strong base. Under these basic conditions, the tosylate of cis-2-methylcyclohexanol eliminates to give mostly 1-methylcyclohexene, but the tosylate of trans-2-methylcyclohexanol eliminates to give only 3-methylcyclohexene. Explain how this stereochemical difference in reactants controls a regiochemical difference in the products of the basic elimination, but not in the acid-catalyzed elimination.

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Textbook Question

Show how you would accomplish the following synthetic conversions.

(d)

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Textbook Question

Predict the esterification products of the following acid/alcohol pairs.

(a) CH₃CH₂CH₂COOH + CH₃OH

(b) CH₃OH + HNO₃

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Textbook Question

Predict the major products of dehydration catalyzed by sulfuric acid.