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Ch. 14 - Ethers, Epoxides, and Thioethers
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh. 14 - Ethers, Epoxides, and ThioethersProblem 20e
Chapter 14, Problem 20e

Show how you would accomplish the following transformations. Some of these examples require more than one step.
(e) 2-chlorohexan-1-ol → 1,2-epoxyhexane

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1
Step 1: Recognize that the transformation involves converting a 2-chlorohexan-1-ol into 1,2-epoxyhexane. This requires the formation of an epoxide, which typically involves an intramolecular reaction of a halohydrin.
Step 2: Begin by identifying the functional groups in the starting material. 2-chlorohexan-1-ol contains both a hydroxyl (-OH) group and a chloro (-Cl) group on adjacent carbons, which is ideal for epoxide formation.
Step 3: Treat the compound with a base, such as sodium hydroxide (NaOH). The base will deprotonate the hydroxyl group, forming an alkoxide ion (R-O⁻). This alkoxide ion is a strong nucleophile.
Step 4: The alkoxide ion will perform an intramolecular nucleophilic substitution (S_N2 mechanism) on the carbon bearing the chlorine atom. This results in the formation of the epoxide ring (1,2-epoxyhexane) and the elimination of the chloride ion (Cl⁻).
Step 5: Verify the stereochemistry of the product, if applicable, as the S_N2 mechanism can lead to inversion of configuration at the carbon where substitution occurs. Ensure the final product matches the desired structure of 1,2-epoxyhexane.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. In the transformation from 2-chlorohexan-1-ol to 1,2-epoxyhexane, the chlorine atom acts as a leaving group, allowing a nucleophile to attack the carbon atom and facilitate the formation of a new bond.
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Nucleophiles and Electrophiles can react in Substitution Reactions.

Epoxidation

Epoxidation is the process of converting alkenes into epoxides, which are three-membered cyclic ethers. This transformation typically involves the reaction of an alkene with a peracid, leading to the formation of an epoxide. In the context of the given transformation, the formation of 1,2-epoxyhexane from 2-chlorohexan-1-ol may involve an intermediate alkene that undergoes epoxidation.
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Stereochemistry

Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the transformation to 1,2-epoxyhexane, understanding the stereochemistry is crucial, as the formation of the epoxide can lead to different stereoisomers depending on the configuration of the starting material and the reaction conditions.
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Related Practice
Textbook Question

Show how you would accomplish the following transformations. Some of these examples require more than one step.

(a) 2-methylpropene → 2,2-dimethyloxirane

(b) 1-phenylethanol → 2-phenyloxirane

(c) 5-chloropent-1-ene → tetrahydropyran

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Textbook Question

Propose mechanisms for the epoxidation and ring-opening steps of the epoxidation and hydrolysis of trans-but-2-ene shown above. Predict the product of the same reaction with cis-but-2-ene.

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Textbook Question

The 2001 Nobel Prize in Chemistry was awarded to three organic chemists who have developed methods for catalytic asymmetric syntheses. An asymmetric (or enantioselective) synthesis is one that converts an achiral starting material into mostly one enantiomer of a chiral product. K. Barry Sharpless (The Scripps Research Institute) developed an asymmetric epoxidation of allylic alcohols that gives excellent chemical yields and greater than 90% enantiomeric excess.

The Sharpless epoxidation uses tert-butyl hydroperoxide, titanium(IV) isopropoxide, and a dialkyl tartrate ester as the reagents. The following epoxidation of geraniol is typical.

(a) Which of these reagents is most likely to be the actual oxidizing agent? That is, which reagent is reduced in the reaction? What is the likely function of the other reagents?

(b) When achiral reagents react to give a chiral product, that product is normally formed as a racemic mixture of enantiomers. How can the Sharpless epoxidation give just one nearly pure enantiomer of the product?

(c) Draw the other enantiomer of the product. What reagents would you use if you wanted to epoxidize geraniol to give this other enantiomer?

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Textbook Question

Show how you would use a protecting group to convert 4-bromobutan-1-ol to hept-5-yn-1-ol.

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Textbook Question

Show how you would accomplish the following transformations. Some of these examples require more than one step.

(d) 5-chloropent-1-ene → 2-methyltetrahydrofuran 

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Textbook Question

Cellosolve® is the trade name for 2-ethoxyethanol, a common industrial solvent. This compound is produced in chemical plants that use ethylene as their only organic feedstock. Show how you would accomplish this industrial process.

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