Ch.14 Some Compounds with Oxygen, Sulfur, or a Halogen

McMurry - Fundamentals of General, Organic, and Biological Chemistry 8th Edition

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McMurry 8th Edition

Ch.14 Some Compounds with Oxygen, Sulfur, or a Halogen

Problem 46e

Chapter 14, Problem 46e

The following alkenes can be prepared by dehydration of an appropriate alcohol. Show the structure of the alcohol in each case that would provide the alkene shown as the major product.
e. 1,4-Pentadiene

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Identify the alkene structure: 1,4-Pentadiene is a diene with double bonds located between carbons 1 and 2, and carbons 4 and 5 in a five-carbon chain. The structure is CH₂=CH-CH₂-CH=CH₂.

Recall the dehydration reaction: Dehydration of an alcohol involves the removal of a water molecule (H₂O) to form a double bond. This typically occurs under acidic conditions and heat.

Determine the alcohol precursor for each double bond: For the double bond between carbons 1 and 2, the alcohol precursor would have an -OH group on carbon 1. For the double bond between carbons 4 and 5, the alcohol precursor would have an -OH group on carbon 4.

Combine the alcohol precursors: The alcohol that would yield 1,4-Pentadiene as the major product must have hydroxyl groups (-OH) on both carbon 1 and carbon 4. The structure of the alcohol is HO-CH₂-CH₂-CH₂-CH(OH)-CH₃.

Verify the reaction: When this alcohol undergoes dehydration, the removal of water molecules from carbons 1 and 2, and carbons 4 and 5, will result in the formation of 1,4-Pentadiene as the major product.

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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, resulting in the formation of an alkene. This process typically requires an acid catalyst and can lead to the formation of multiple products, but the major product is determined by the stability of the resulting alkene, often following Zaitsev's rule.

Zaitsev's Rule

Zaitsev's rule states that in elimination reactions, the more substituted alkene is usually the major product. This is because more substituted alkenes are generally more stable due to hyperconjugation and the inductive effect, making it essential to consider the structure of the alcohol to predict the major alkene formed.

Structure of Alkenes

Alkenes are hydrocarbons that contain at least one carbon-carbon double bond. The structure of an alkene, such as 1,4-pentadiene, is crucial for understanding how to derive the corresponding alcohol. The positioning of the double bonds in the alkene influences the choice of alcohol for dehydration, as the alcohol must have the appropriate carbon skeleton to yield the desired alkene.

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The following alkenes can be prepared by dehydration of an appropriate alcohol. Show the structure of the alcohol in each case that would provide the alkene shown as the major product.e. 1,4-Pentadiene

Verified video answer for a similar problem:

Key Concepts

Dehydration Reaction

Zaitsev's Rule

Structure of Alkenes

The following alkenes can be prepared by dehydration of an appropriate alcohol. Show the structure of the alcohol in each case that would provide the alkene shown as the major product.
e. 1,4-Pentadiene