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 43a,b,c
Predict the major products of dehydration catalyzed by sulfuric acid.
(a) hexan-1-ol
(b) hexan-2-ol
(c) pentan-3-ol
Verified step by step guidance1
Step 1: Understand the dehydration reaction. Dehydration of alcohols involves the removal of a water molecule, typically catalyzed by an acid like sulfuric acid. The reaction proceeds via the formation of a carbocation intermediate, and the major product is determined by the stability of the carbocation and the Zaitsev rule (favoring the more substituted alkene).
Step 2: Analyze hexan-1-ol (structure B). Hexan-1-ol is a primary alcohol. Upon dehydration, it forms a carbocation at the first carbon, which is unstable. Rearrangement does not occur, and the major product will be the least substituted alkene, 1-hexene.
Step 3: Analyze hexan-2-ol (structure C). Hexan-2-ol is a secondary alcohol. Upon dehydration, it forms a carbocation at the second carbon. This carbocation is relatively stable, and the major product will be the more substituted alkene, 2-hexene, following the Zaitsev rule.
Step 4: Analyze pentan-3-ol (structure A). Pentan-3-ol is a secondary alcohol. Upon dehydration, it forms a carbocation at the third carbon. This carbocation is stable, and the major product will be the more substituted alkene, 3-pentene, following the Zaitsev rule.
Step 5: Summarize the major products. For hexan-1-ol, the major product is 1-hexene. For hexan-2-ol, the major product is 2-hexene. For pentan-3-ol, the major product is 3-pentene. These products are formed based on carbocation stability and the Zaitsev rule.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Dehydration Reaction
A dehydration reaction involves the removal of a water molecule from an alcohol to form an alkene. This process typically requires an acid catalyst, such as sulfuric acid, which protonates the alcohol, making it a better leaving group. The resulting carbocation can then undergo elimination to form a double bond, leading to the formation of alkenes as major products.
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General Reaction of Dehydration with POCl3
Carbocation Stability
The stability of carbocations is crucial in determining the major products of dehydration reactions. Tertiary carbocations are more stable than secondary, which are more stable than primary. The formation of the most stable carbocation intermediate during the reaction pathway will favor the formation of the corresponding alkene, influencing the product distribution.
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Markovnikov's Rule
Markovnikov's Rule states that in the addition of HX to an alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached. This principle also applies to dehydration reactions, where the more substituted alkene is typically the major product due to the stability of the carbocation formed during the reaction.
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Related Practice
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
(c) 2 CH3CH2OH + H3PO4
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Textbook Question
Show how you would accomplish the following synthetic conversions.
(a)
(b)
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Textbook Question
Show how you would accomplish the following synthetic conversions.
(c)
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