13-8 (CHCH-CHCHCH.CHOHCHCHCHO OH CaHCH-CH C CHCH,CCH (3)CH:CH-CH2 HBr CHCHBrMCO CH CHCOOH CH3 CH3 4⊙→0u→om&Go,0:O0 6⊙→⊙a→⊙HC→产物 分0H→0C,s压产物 分)由)2c,HC,cH,oH0产物 ⊙cH=c4→c94o+9HH:7→94c0aH8出 0 ,BC4产物 00→0S0H一→002产物 I0)O-CH,→Br-OCH,→BrO-CH,C →Br-OCH,OH→Br-CH2ONa O→OQ+0N-Qa①cHo产物 NO2 mO-oH→○-0H→Ccc0Q产物 7 13-8 C2H5 C2H5 OH C2H5 (1) CH=CH2 B2H6 /THF H2O2 /OH- CH2CH2 CrO3 -❜✲❝ CH2CHO C2H5 C2H5 (2 ) CH=CH2 H2O/H + CHCH3 OH C2H5CCH3 O -H2 Cu CH3 CH3 (3) CH3CH=CH2 HBr CH3CHBr H2O/H + CH3CHCOOH Mg/
CO2 (2) (1) (4) OH OH O K2Cr2O7 /H2SO4 (5) Cl OH Cl2/Fe

OH 6 OCH3 CH2=CH2 AlCl3 Br2 /Fe  71 2C2H5CH2CH2OH
H2SO4 - H2O C2H5 OH OH ❞❢❡ (8) CH2=CH2 CH2 CH2 O HOH CH2 CH2 OH OH CH2 CH2 O CH2 CH2 O CH2 CH2 Na Br SO3H OH
(9 ) Br NaOH/H2O CH2CH=CH2 CH3 CH3 Cl
B CH2 r Cl (10) Br Br CH2OH Br CH2ONa Cl NO2 O2N Br CH2ONa ❣❤ OH OH (11) O CH3CO3H