Question

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

Short answer

Answer: To prepare ethyl hexyl ether using the Williamson ether synthesis, react the ethoxide ion (C2H5O-) generated from sodium ethoxide (C2H5ONa) and ethanol (C2H5OH) with 1-hexyl bromide (C6H13Br), forming ethyl hexyl ether (C2H5OC6H13) as the final product.

Step-by-step solution

Identify starting materials

First, we need to identify the starting materials for the formation of ethyl hexyl ether (C2H5OC6H13). The ether can be formed by the reaction of ethoxide ion (C2H5O-) with a hexyl halide (C6H13X) or by the reaction of a hexoxide ion (C6H13O-) with an ethyl halide (C2H5X).

Select appropriate alkoxide and alkyl halide

To minimize the risk of elimination reactions, it is important to select a primary alkyl halide. We'll use ethoxide ion (C2H5O-) and 1-hexyl bromide (C6H13Br) as our starting materials. The ethoxide ion can be generated from the reaction of sodium ethoxide (C2H5ONa) with ethanol (C2H5OH). Sodium ethoxide can be prepared from the reaction of sodium metal with ethanol.

Generate the ethoxide ion

To generate the ethoxide ion (C2H5O-), first, dissolve sodium metal in ethanol. The reaction is as follows: 2Na + 2C2H5OH -> 2C2H5ONa + H2

Perform the Williamson ether synthesis

Now that we have the ethoxide ion (C2H5O-), it can be reacted with 1-hexyl bromide (C6H13Br) to give ethyl hexyl ether (C2H5OC6H13). The reaction is as follows: C2H5O^- + C6H13Br -> C2H5OC6H13 + Br^- This is the Williamson ether synthesis reaction that forms ethyl hexyl ether as the final product.