Textbook Question
Predict the esterification products of the following acid/alcohol pairs.
(d)
(e)
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Ch.11 - Reactions of Alcohols
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 11, Problem 44a,b,c
Predict the esterification products of the following acid/alcohol pairs.
(a) CH3CH2CH2COOH + CH3OH
(b) CH3OH + HNO3
(c) 2 CH3CH2OH + H3PO4
Verified step by step guidance1
Step 1: Understand the esterification reaction. Esterification is a chemical reaction between a carboxylic acid and an alcohol, typically in the presence of an acid catalyst, to form an ester and water. For phosphoric acid (H3PO4), it can react with alcohols to form phosphate esters.
Step 2: Analyze pair (a): CH3CH2CH2COOH (butanoic acid) reacts with CH3OH (methanol). The hydroxyl group (-OH) from the carboxylic acid and the hydrogen atom from the alcohol's hydroxyl group combine to form water (H2O). The remaining parts form the ester. The ester will have the structure CH3CH2CH2COOCH3.
Step 3: Analyze pair (b): CH3OH (methanol) reacts with HNO3 (nitric acid). Nitric acid can act as an acid in esterification reactions. Methanol will donate its hydroxyl group (-OH), and nitric acid will contribute its -NO3 group to form methyl nitrate (CH3ONO2). Water is also produced.
Step 4: Analyze pair (c): 2CH3CH2OH (ethanol) reacts with H3PO4 (phosphoric acid). Phosphoric acid can form mono-, di-, or tri-esters depending on the number of alcohol molecules reacting. In this case, two ethanol molecules react to form diethyl phosphate ((CH3CH2O)2PO2H) and water.
Step 5: Summarize the general process for esterification: Identify the acid and alcohol, determine the parts that combine to form water, and write the structure of the ester formed by combining the remaining fragments. Ensure proper naming and structural representation of the products.
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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.
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Carboxylic Acids
Carboxylic acids are organic compounds characterized by the presence of one or more carboxyl groups (-COOH). They are known for their acidic properties and can react with alcohols to form esters through esterification. The structure and reactivity of carboxylic acids are crucial for predicting the products of reactions involving these compounds.
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Alcohols
Alcohols are organic compounds that contain one or more hydroxyl (-OH) groups attached to a carbon atom. They can act as nucleophiles in esterification reactions, where their hydroxyl group attacks the carbonyl carbon of a carboxylic acid. The type of alcohol used can influence the structure and properties of the resulting ester.
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Related Practice
Textbook Question
Show how you would convert (S)-hexan-2-ol to
(a) (S)-2-chlorohexane.
(b) (R)-2-bromohexane.
(c) (R)-hexan-2-ol.
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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 major products of dehydration catalyzed by sulfuric acid.
(a) hexan-1-ol
(b) hexan-2-ol
(c) pentan-3-ol
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Textbook Question
Show how you would accomplish the following synthetic conversions.
(c)
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