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1 Conversion 08 How Many of the following have 4 stereo-isomers & total monobromo derivative possible for (85) is 2 3 3 2 2 2 3 2 4 HBr Na Al O HNO Fe/HCl NaOH 3 6 (PhCOO) Et O Cr O , H SO C H (1) (2) (3) (4) (5) (6) − ∆ → → → → → → 3 | CH COCl/Pyridine↓ 2 3 2 2 2 3 3 2 2 4 H /Pd H PO NaNO Br H O HNO EtOH HCl,0 C H O H SO (13) (12) (11) (10) (9) (8) (7) ⊕ ° ← ← ← ← ← ← 2 | HNO /278 K ↓ 2 2 3 7 2 2 4 3 Cu Zn Br dil. O C H Cl HBr H O H SO hv AlCl (14) (15) (16) (17) (18) (19) (20) → ← ← ← ← ← ∆ 3 3 | CH Cl/AlCl ↓ 2 2 3 2 3 2 3 I (CH ) CuLi O NaOH Na H /Ni NaOH Zn/H O (1eq.) Liq.NH (27) (26) (25) (24) (23) (22) (21) ∆ ← ← ← ← ← ← 2 | SOCl ↓ NH3 5 PCl SnCl2 2 H O HCHO(excess) CH CHO 3 HCl NaOH, H (28) (29) (30) (31) (32) (33) (34) → → → → → → ∆ ⊕ 4 | NaBH /MeOH ↓ 2 2 2 6 3 2 4 2 2 H O /NaOH B H O m CPBA DIBAL H SO THF H O (35) (36) (37) (38) (39) (40) (41) − ← ← → → → → ∆ | ↓ 3 2 2 4 2 2 4 EtO NBS Conc. (i) CH MgBr Ba(OH) PCC dil. H SO (ii) H O H SO (49) (48) (47) (46) (45) (44) (43) (42) Θ ∆ ← ← ← ← ← ← ← | ↓ 3 3 2 2 HCl AgCN CHCl Sn CuCN CH CH OH ZnCl KOH HCl KCN 1 2 : (50) (51) (52) (53) (54) (55) (56) (57)Aromatic → → ← ← ← → + | H⊕ ↓ 2 3 3 2 5 2 3 Br Na Cl Kolbe Ag(NH ) PCl hv Et O hv elechrolysis AlCl (65) (64) (63) (62) (61) (60) (59) (58) ⊕ ← ← ← ← ← →  2Be nzene→ | AgF ↓ 2 4 3 2 3 KOH NaOI NaOBr Hg(OAc) NaBH NH (i) R Br EtOH, H O NaOH (ii) H O (66) (67) (68) (69) (70) (71) (72) ⊕ − ∆ ∆ → → → → → → ← H2/Ni Cl /hv then KOH 2 xs (12 mole) (70%) (y gm) (50%) (x gm) (50%) (60%) (80%) (2.2 gm) (z gm)

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