67. Which reaction sequence is required to accomplish the following transformation? 
(A) 1. LiAlH4 2. H3O
3. NaH, then CH3I
(B) 1. H2NNH2, KOH, 120 °C 2. H2, Pd/C 3. NaH, then CH3I
(C) 1. HOCH2CH2OH, H3O
2. LiAlH4 3. NaH, then CH3I, then H3O
(D) 1. HOCH2CH2OH, H3O
2. H2NNH2, KOH, 120 °C 3. H2, Pd/C, H3O
(E) 1. NaNH2, CH3I 2. LiAlH4 3. H2, Pd/C, H3O
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統計: A(8), B(0), C(30), D(6), E(0) #937596
統計: A(8), B(0), C(30), D(6), E(0) #937596
詳解 (共 3 筆)
#4493152
反應物與產物之carbonyl group相同但有其他group被還原,可判斷是先用diol在酸下保護carbonyl group才進行後續還原,僅C.D可選,而後由ester→ether走C(還原後行Williamson ether synthesis)。
註1:B.D中出現的H2NNH2, KOH是Wolff-Kishner rxn,用以將aldehyde/ketone還原為alkane。
註2:E中出現的NaNH2也是強鹼,故NaNH2, CH3I也是Williamson ether synthesis,用以拔alcohol的hydroxyl H形成強nucleophile,打上R(δ+)-X。
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#1154852
標準答案更正為C
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