Final answer:
Neither reagent sequence provided, (e) involving NaOH and (CH₃)₃CCH₂CH₂Br nor (f) involving NH₃ and (CH₃)₃CCH₂CH₂Br, can efficiently accomplish the transformation of an alcohol into an ether due to steric hindrance and the mismatched reactivity of the intermediates.
Step-by-step explanation:
The question you've asked is related to organic chemistry and involves the selection of reagents that can accomplish a specific chemical transformation. Specifically, you wish to know which reagents can convert an alcohol into an ether using a two-step sequence involving either sodium hydroxide (NaOH) or ammonia (NH₃) followed by tert-butyl bromide ((CH₃)₃CCH₂CH₂Br).
For option (e), the first step involves NaOH, which is a strong base and will deprotonate an alcohol to create an alkoxide ion. This ion could then act as a nucleophile in a subsequent reaction. The second step with (CH₃)₃CCH₂CH₂Br would suggest an attempt at the Williamson ether synthesis. However, (CH₃)₃CCH₂CH₂Br with an alkoxide formed from a primary alcohol would not work efficiently due to steric hindrance from the bulky tert-butyl group, making this option unsuitable to accomplish the transformation efficiently.
For option (f), the first step is the use of NH₃ (ammonia), which can also act as a base and a nucleophile. The second step involves reacting the nucleophilic ammonia with (CH₃)₃CCH₂CH₂Br to ultimately form an amine, not an ether, so this sequence would also be unsuccessful for the desired transformation into an ether.
Therefore, neither option (e) nor option (f) as listed is suitable for transforming an alcohol into an ether as desired.