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Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 12, Problem 73c

Identify the alkene and alcohol partners that could be used to make the following ethers.
(c)

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1
Examine the ether structure provided in the image. The ether has two alkyl groups connected by an oxygen atom. Identify these two groups to determine the potential alkene and alcohol partners.
The ether structure shows a tert-butyl group (\(\text{C(CH}_3)_3\)) and an isopropyl group (\(\text{CH(CH}_3)_2\)). These groups are connected by an oxygen atom.
To synthesize this ether, consider the Williamson ether synthesis, which involves an alkoxide ion reacting with a primary or secondary alkyl halide. The alkoxide ion is derived from an alcohol, and the alkyl halide can be derived from an alkene.
Identify the alcohol that could form the alkoxide ion. The tert-butyl group suggests the use of tert-butyl alcohol (\(\text{(CH}_3)_3\text{COH}\)). This alcohol can be deprotonated to form the tert-butoxide ion.
Identify the alkene that could form the alkyl halide. The isopropyl group suggests the use of propene (\(\text{CH}_3\text{CH=CH}_2\)). Propene can be converted to isopropyl bromide through a hydrohalogenation reaction, which can then react with the tert-butoxide ion to form the ether.

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Key Concepts

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

Ethers

Ethers are organic compounds characterized by an oxygen atom connected to two alkyl or aryl groups. They can be synthesized through various methods, including the reaction of an alcohol with an alkene in the presence of an acid catalyst. Understanding the structure and reactivity of ethers is essential for identifying the appropriate alkene and alcohol partners for synthesis.
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Alkenes

Alkenes are hydrocarbons that contain at least one carbon-carbon double bond, making them unsaturated. Their reactivity is primarily due to this double bond, which can participate in various reactions, including electrophilic addition. Recognizing the structure and reactivity of alkenes is crucial for determining which alkenes can react with alcohols to form ethers.
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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 reactions with alkenes, leading to ether formation. Understanding the properties and reactivity of alcohols is vital for selecting the correct alcohol partner in ether synthesis.
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