Organic Lab Reactions 211

Organic Lab Reactions 211 - (U) C 2 H 6 C 2 H 6 t-C 3 H 7...

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206 REDUCTION WITH ALUMINUM ALKOXIDES TABLE I REDUCTION OF ALDEHYDES WITH ALUMINUM ALKOXIDES Compound Reduced Product Formed Reagent and Solvent * R in A1(OR) 3 Refer- ence (a) Aliphatic Aldehydes Dichloroacetaldehyde Chloral Bromal Butyraldehyde a,a,/3-TrichIorobutyralde- hyde Aldol 1 Crotonaldehyde a-Chlorocrotonaldehyde a-Bromocrotonaldehyde 2,4-Hexadienal-l 2,4,6-Octatrienal-l 2,4,6,8-Decatetraenal-l Citral Citronellal Hydroxycitronellal Dichloroethyl alcohol Trichloroethyl alcohol Tribromoethyl alcohol Butyl alcohol 2,2,3-Trichlorobutanol-l 1,3-Dihydroxybutane Crotyl alcohol 2-Chloro-2-butenol-l 2-Bromo-2-butenol-l 2,4-Hexadienol-l 2,4,6-Octatrienol-l 2,4,6,8-Decatetraenol-l Geraniol (24%) Nerol (44%) Citronellol Hydroxycitronellol i-C 3 H 7 (D) C2H6 i-C 3 H 7 (C) C 2 H 5 t-C 3 H 7 (benzene) i-C 3 H 7 (i-C 3 H 7 OH) C2H5 (benzene) C 2 H 6 C 2 H 6 (25°) i-C 3 H 7
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Unformatted text preview: (U) C 2 H 6 C 2 H 6 t-C 3 H 7 (D) f-C 3 H 7 (D) i-C 3 H 7 (D) i-C 3 H 7 (U or D) i-C 3 H 7 (U) C 2 H 6 C 2 H 6 60% 85% 77-90% 69% 19-28% 30-36% 6% 92% 30% 60-65% 64% 70% 1 0Q07 32% 60% 78% 59 2,15,60 5,6V 2 13 13 13 2 ' 12 12, 13 12 12 62 62 62 Q CO o t Do 13 1 12 (6) Alicyclic and Aromatic Aldehydes A s-Tetrahydrobenzalde-hyde A 3-6-Methyltetrahydro-benzaldehyde A 3-Tetrahydrobenzyl alcohol A 3-6-Methyltetrahydro-benzyl alcohol NOTE: References 59-80 appear on p. 221 * If no Bolvent is listed the alcohol corresponding to the alkoxide was used. C refers to clarified aluminum isopropoxide but not distilled; D, to distilled reagent; and U, to an untreated solution of the alkozida (see p. 199)....
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