.( . ) 1 , . 2 CH3 OH CH2 CH2 CH2 CH OH OH OH -1,2 ) OH CH2 OH -1,2,3 ) 3 1 4 CH3CH2OH CH3CH2CH2OH CH3CHCH3 -1 ) ( OH ) -2 ) 5 CH3 CH3CH2CH2CH2 OH -1 CH3CH2CHCH3 OH -2 CH3 CH3CHCH2 CH3 C OH 2- CH3 OH -1 2- -2 6 2 CH3CH CH2 + H2O H+ CH3CHCH3 OH -2 7 CH3CH2CH2Br + KOH CH3CH2CH2OH + KBr 8 O CH3 C CH3 C O + H2 Ni CH3CH2OH H CH3 + H2 Ni CH3CHCH3 OH -2 9 3 CH3CH2OH J Bump 10 CH3OH 1946 11 R R O H O R H O H 12 4 R + CH2 '+ .. O H 13 2CH3CH2OH + 2Na CH3OK + H2O 2CH3CH2ONa + H2 CH3OH + KOH CH3CH2OH + NaOH CH3CH2ONa + H2O 14 H CH3CH2OH + HCl CH3CH2 O Cl- H 15 5 H .. CH3CH2OH + H+ CH3CH2 O H 16 I- + + H ICH2CH3 + HOH CH3CH2 O H 17 CH3CH2CH2OH + PCl5 CH3CH2CH2Cl + POCl3 + HCl -1 1- 3CH3CH2CH2CH2Br + H3PO3 3CH3CH2CH2CH2OH + PBr3 -1 CH3CHCH3 + SOCl2 1- CH3CHCH3 + HCl + SO2 OH Cl -2 218 6 + CH3O-Na+ + CH3CH2CH2 Cl CH3OCH2CH2CH3 + NaCl 1- 19 CH3CH2OH + HOSO3H + CH3CH2OSO3H + H2O O O CH3OH + CH3 C CH3O C CH3 + H2O OH 20 2CH3CH2OH H+ CH3CH2OCH2CH3 + H2O 21 7 H .. CH3CH2OH + H+ CH3CH2 O H 22 H + CH3CH2OH + CH3CH2 O H CH3CH2O CH2CH3 -H+ -H2O CH3CH2OCH2CH3 H 23 CH3 CH3 C CH3 CH2CH3 H+ CH3 C CHCH3 + H2O OH 2- -2 2- -2 24 8 O O CH3CH2OH [O] CH3 C [O] CH3 C H OH 25 CH3 H C CH3 [O] OH CH3 C CH3 O -2 -2 ) 26 ClCH2CH2Cl + 2KOH CH2CH2 + 2KCl 1,2- OH OH -1,2 27 9 CH3CH CH2 KMnO4 CH3 CH OH CH2 OH -1,2 28 H CH2OH H2C 2 CHOH + Cu(OH)2 -2H O 2 CH2OH HC HOH2C O O Cu O O CH2 CH CH2OH H (II) 29 CH2OH CHOH + 3HNO3 CH2OH CH2ONO2 H2SO4 CHONO2 + 3H2O CH2ONO2 30 10 , , , 31 32 33 11 CH2 CH + CH3 AlCl3, HCl, 100°C CH3 O2, 95-130°C H2SO4, 50-90°C + CH CH3 CH3 C CH3 O CH3 C CH3 O OH OH 34 OH ONa SO3Na NaOH, SO3Na . HCl -NaCl ONa OH 35 OH - - - C6H5OH + KOH C6H5OK + CO2 + H2O C6H5OK + H2O C6H5OH + KHCO3 36 12 + C6H5O-K+ + CH3 C6H5OCH3 + KBr Br 37 Br OH OH + 3Br2 + Br 3HBr Br 38 O OH OH [O] [O] O OH 39 13 (III) 40 14