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b) Because direct nucleophilic substitution cannot be effected on a benzene ring, the conjugate base of phenol must be reacted with the primary alkyl halide. OH 1) NaOH OCH₂CH₂CH₃ 2) CH₃CH₂CH₂Br c) To avoid predominant E2 elimination, the conjugate base of the secondary alcohol must be reacted with the primary alkyl halide. OH 1) Na O 2) Br 10.9 OCH₃ CH₃ a) b) c) Ph₂CHOCH₂CH₂Cl CH₃ 10.10 H : CH₃(CH₂)₃CH₂-OH +: SN2 HO-CH₂(CH₂)₃CH₃ H₂O: H 149