COCl CH3 CH3 Br CH3 HNO3 Br2 H2SO 4 Fe° Br K 2Cr2O7 H2SO 4 NO2 NO2 SOCl2 NO2 COOH Br H2SO 4 CONH2 NO2 H2SO 4 NaOH COOC2H5 Br COO- Na+ COO- K+ Br Br NO2 NO2 NO2 O COCl 1) CH3MgBr 1) Mg° Br 2) CO 2 3) HCl, H2O OH PBr 3 2) HCl, H2O K 2Cr2O7 H2SO 4 OH NO2 C2H5OH 2) NH3 KOH NO2 Br CH3OH 1) SOCl2 Br COOCH3 SOCl2 COOH COOCH3 H2SO 4 1) SOCl2 CONH2 CH3OH C2H5OH 2) NH3 KOH COO- K+ NaOH H2SO 4 COO- Na+ COOC2H5 HBr Ph Ph Br Peroxide Ph 1) Mg° 2) CO2 3) HCl, H2O CH3OH KOH Ph Ph Br 1) SOCl2 Ph Ph NBS C2H5OH KOH H2SO 4 NaOH CONH2 Ph Ph COOC2H5 Ph Ph 1) Li° 2) CuI 3) CH3CH2CH2Br COOCH3 H2SO 4 COOH 2) NH3 Ph COCl SOCl2 COO- Na+ COO- K+ Br COCl Br DBr CH3 D Peroxide 1) Mg° 2) CO2 3) HCl, H2O CH3 CH3OH D H2SO 4 COOCH3 D 1) SOCl2 CONH2 OH D CH3 2) NH3 KOH CH3 NaOH COO- K+ D O CH3 COOH H2SO 4 1) CH3MgBr 2) HCl, H2O D SOCl2 CH3 CH3 C2H5OH H2SO 4 COOC2H5 D COO- Na+ D CH3 CH3 PBr 3 1) Mg° 2) CO2 3) HCl, H2O Br OH COCl SOCl2 CH3OH COOCH3 COOH 1) SOCl2 H2SO 4 C2H5OH 2) NH3 KOH CONH2 H2SO 4 NaOH COOC2H5 COO- Na+ COO- K+ Ph CH3MgBr Ph Ph 1) CO2 2) HCl, H2O C C MgBr Ph CH3OH C C H Ph 1) NBS 2) KOH 3) Br2 4) KOH 1) SOCl2 Ph PBr 3 KOH C C COO- K+ Br H2SO 4 NaOH Ph Ph COCl 1) Mg° 2) CO2 3) HCl, H2O SOCl2 COOCH3 H2SO 4 1) SOCl2 C2H5OH 2) NH3 CONH2 C C COOC2H5 C C COO- Na+ COOH Br C C COOCH3 H2SO 4 CH3OH 1) Mg° 2) CH3CHO 3) HCl, H2O C C COCl C2H5OH C C CONH2 Ph Ph C C COOH 2) NH3 CH2CH3 OH SOCl2 KOH COO- K+ NaOH H2SO 4 COO- Na+ COOC2H5 CH2COCl CH2Br CH2CN Cl Cl Cl KCN SOCl2 HCl, H2O Cl Cl CH2COOH Cl CH2COOCH3 Cl CH3OH Cl 1) Cl2, Fe° 2) Cl2, Fe° 3) NBS CH3 H2SO 4 1) SOCl2 Cl KOH Cl CH2COO- Na+ Cl Cl CH2COOC2H5 H2SO 4 NaOH CH2COO- K+ Cl Cl C2H5OH CH2CONH2 2) NH 3 Cl Cl Cl Cl COCl Br 1) Mg° 2) CO2 3) HCl, H2O PBr 3 SOCl2 COOH OH COOCH3 CH3OH H2SO 4 1) SOCl2 1) Mg° 2) Benzaldehyde 3) HCl, H2O Br CONH2 C2H5OH 2) NH3 KOH COO- K+ NaOH H2SO 4 COO- Na+ COOC2H5 Ph Ph 1) Mg° 2) CO2 3) HCl, H2O Br KOH SOCl2 Ph Br COOCH3 CH3OH Ph Ph COCl COOH Br H2SO 4 1) SOCl2 C2H5OH 2) NH3 NBS Ph Ph KOH CONH2 H2SO 4 NaOH Ph COOC2H5 Br Ph Ph 1) Li° 2) CuI 3) Br COO- NA+ COO- K+ Br PhCH 2Br Ph Ph 1) Mg° 2) CO2 3) HCl, H2O Br PBr 3 COCl SOCl2 CH3OH Ph PhCH 2CH2OH 1) Mg° 2) Ethylene Oxide 3) HCl, H2O PhBr COOH H2SO 4 Ph COOCH3 1) SOCl2 2) NH3 Ph CONH2 C2H5OH KOH NaOH H2SO 4 Ph Ph COO- K+ Ph COO- Na+ COOC2H5 COCl Ph OC2H5 Br Ph 1) Mg° 2) CO2 3) HCl, H2O OC2H5 PBr 3 SOCl2 CH3OH COOH Br Ph Ph OC2H5 CONH2 2) NH3 1) Mg° Ph 2) PhCH2CHO 3) HCl, H2O H2SO 4 OC2H5 C2H5OH KOH NaOH H2SO 4 COO- K+ OC2H5 COOCH3 Ph OC2H5 Ph Br OC2H5 1) SOCl2 COOC2H5 Ph OC2H5 OC2H5 COO- Na+ PCC Ph OC2H5 Br2, Fe° PhCH 2CH2OH OC2H5 1) Mg° 2) Ethylene Oxide 3) HCl, H2O PhBr 1) NaOH 2) CH3CH2Br OH Br COCl 1) Mg° 2) CO2 3) HCl, H2O SOCl2 CH3OH COOH H2SO 4 COOCH3 1) SOCl2 CONH2 2) NH3 C2H5OH KOH NaOH H2SO 4 COO- K+ COO- Na+ COOC2H5 COCl 1) Mg° 2) CO2 3) HCl, H2O Br PBr 3 SOCl2 CH3OH COOCH3 OH COOH H2SO 4 1) SOCl2 1) Mg° 2) CH2O 3) HCl, H2O C2H5OH 2) NH3 CONH2 KOH NaOH H2SO 4 COOC2H5 Br COO- K+ COO- Na+ COCl Br Br Br Br CH3 Br Br Br CH3 K 2Cr2O7 H2SO 4 Br CH3 Br2 Fe° CONH2 Br 1) SOCl2 Br Br Br Br COOCH3 CH3OH Br 2) NH3 NaOH H2SO 4 COO- K+ Br Br Br Br COO- K+ Br Br COOC2H5 Br CONH2 Br COOCH3 C2H5OH KOH Br H2SO 4 COOH CH3 Br COCl SOCl2 COOH COO- Na+ Br Br Br Br COO- Na+ Br Br Br Br COOC2H5 COCl Br 1) Mg° 2) CO2 3) HCl, H2O Br2 Fe° SOCl2 COOCH3 COOH CH3OH H2SO 4 1) SOCl2 C2H5OH CONH2 2) NH3 Cl KOH NaOH COOC2H5 H2SO 4 AlCl3 COO- Na+ COO- K+ 1) Mg° 2) CO2 3) HCl, H2O Br COCl SOCl2 CH3OH PBr 3 OH H2SO 4 COOH 1) SOCl2 COOCH3 C2H5OH 2) NH3 KOH NaOH CONH2 H2SO 4 COOC2H5 COO- K+ O COO- Na+ K 2Cr2O7 H2SO 4 OH 1) CH3CH2CH2CH2MgBr 2) HCl, H2O H PCC O OH