Outline a method of synthesizing \(\alpha\) -phenylethyl tert-buty1 ether from styrene and tert-butyl alcohol. Any inorganic reagents may be employed.

Short Answer

Expert verified
To synthesize α-phenylethyl tert-butyl ether from styrene and tert-butyl alcohol, follow these steps: 1. Deprotonate tert-butyl alcohol with sodium hydride (NaH) to form the tert-butoxide ion: \[ tert\text{-}butyl\,alcohol + NaH \rightarrow tert\text{-}butoxide\,Na+ + H_2 \] 2. React styrene with N-bromosuccinimide (NBS) for benzylic bromination to produce α-phenylethyl bromide: \[ styrene + NBS \rightarrow \alpha\text{-}phenylethyl\,bromide \] 3. Perform Williamson Ether Synthesis by reacting the tert-butoxide ion with α-phenylethyl bromide, resulting in the desired ether product and a by-product: \[ tert\text{-}butoxide\,Na+ + \alpha\text{-}phenylethyl\,bromide \rightarrow \alpha\text{-}phenylethyl\,tert\text{-}butyl\,ether + NaBr \]

Step by step solution

01

Formation of tert-butoxide ion from tert-butyl alcohol

To form the tert-butoxide ion from tert-butyl alcohol, we need to deprotonate the alcohol with a strong base, such as sodium hydride (NaH). The reaction takes place as follows: \[ tert\text{-}butyl\,alcohol + NaH \rightarrow tert\text{-}butoxide\,Na+ + H_2 \] This generates the sodium salt of the tert-butoxide ion.
02

Formation of alkyl halide from styrene

To prepare an alkyl halide from styrene, we need to react it with a suitable halogenation reagent. In this case, we can use N-bromosuccinimide (NBS) as the halogenating agent. The reaction proceeds via radical bromination of the styrene molecule at the benzylic position, generating the desired benzyl bromide. The process can be written as: \[ styrene + NBS \rightarrow \alpha\text{-}phenylethyl\,bromide \]
03

Williamson Ether Synthesis for the final product formation

With the tert-butoxide ion and the α-phenylethyl bromide in hand, we can now proceed to perform Williamson Ether Synthesis to form the desired ether product. This involves the nucleophilic attack of the alkoxide ion on the alkyl halide, leading to the formation of the ether product and a by-product. The reaction can be represented as: \[ tert\text{-}butoxide\,Na+ + \alpha\text{-}phenylethyl\,bromide \rightarrow \alpha\text{-}phenylethyl\,tert\text{-}butyl\,ether + NaBr \] This reaction yields the desired product, α-phenylethyl tert-butyl ether.

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