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11.19 O a) H₂O HC=C: Br H₂SO₄ O 1) disiamylborane as part (a) b) H 2) H₂O₂, , NaOH O H₂O c) H₂SO₄ 1) NaNH₂ 2) Br as part (a) 11.20 This reaction will produce the H CH₃CH₂ CH₂CH₂CH₃ (S)-enantiomer of the alcohol. C OH 11.21 Use (S,S)-trans-2,5-dimethylborolane the enantiomer of the borolane shown in the text, to produce (R)-2-butanol, the enantiomer of the alcohol shown in the text. 11.22 CI CH₂ CH₂ C a) C C H b) C C CH₃ c) CBr₂ d) H₃C C CH₂ H CH₃ H H CH₃ 175