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Chapter 11: Problem 4

Show how ethyl hexyl ether might be prepared by a Williamson ether synthesis.

Short Answer

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Question: Show how ethyl hexyl ether can be prepared using Williamson ether synthesis. Answer: Ethyl hexyl ether can be prepared by reacting sodium ethoxide (CH3CH2ONa) with hexyl bromide (CH3CH2CH2CH2CH2CH2Br) through Williamson ether synthesis. The resulting product will be ethyl hexyl ether (CH3CH2OCH2CH2CH2CH2CH2CH2) and sodium bromide (NaBr).

Step by step solution

01

Determine the structure of ethyl hexyl ether

Ethyl hexyl ether has an ethyl group (CH3CH2) and a hexyl group (CH3CH2CH2CH2CH2CH2) connected by an ether oxygen atom. As a result, the structure can be represented as CH3CH2OCH2CH2CH2CH2CH2CH2.
02

Choose the alkoxide ion and alkyl halide

We can choose either an ethoxide ion or a hexoxide ion as the alkoxide ion, and an ethyl halide or a hexyl halide as the alkyl halide. Let's use sodium ethoxide (CH3CH2ONa) as the alkoxide ion and a hexyl halide (hexyl bromide) as the alkyl halide. Sodium ethoxide can be prepared by reacting ethanol with sodium metal. Hexyl bromide can be prepared by reacting 1-hexanol with a halogenating agent such as PBr3 or HBr.
03

Write the Williamson ether synthesis reaction

Now, we can write the reaction of sodium ethoxide with hexyl bromide to form ethyl hexyl ether: CH3CH2ONa + CH3CH2CH2CH2CH2CH2Br -> CH3CH2OCH2CH2CH2CH2CH2CH2 + NaBr This completes the preparation of ethyl hexyl ether using Williamson ether synthesis.

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