Which of the following will successfully synthesize the given target?

• A.
• B.
• C.
• D.

Answer: (C)

Verified step by step guidance

1. Identify the target molecule: The target molecule is an ether with a phenyl group attached to an oxygen atom, which is connected to a chiral carbon bearing a cyclopropyl group and a tert-butyl group.
2. Analyze the first reaction: The first reaction involves a phenyl bromide and an alcohol in the presence of NaH and THF. NaH is a strong base that can deprotonate the alcohol to form an alkoxide ion, which can then perform a nucleophilic substitution on the phenyl bromide to form an ether.
3. Analyze the second reaction: The second reaction is similar to the first, with a slight difference in the structure of the alcohol. The same mechanism applies, where NaH deprotonates the alcohol to form an alkoxide, which then attacks the phenyl bromide.
4. Analyze the third reaction: The third reaction involves phenol and an alkyl bromide in the presence of NaOH and water. NaOH can deprotonate phenol to form a phenoxide ion, which can then perform a nucleophilic substitution on the alkyl bromide to form an ether.
5. Analyze the fourth reaction: The fourth reaction is similar to the third, with a different stereochemistry of the alkyl bromide. The mechanism remains the same, where NaOH deprotonates phenol to form a phenoxide ion, which attacks the alkyl bromide.