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2. 2 : 2, , 3. 2 3 4. 2 4 5. 2 5 6. CH3 O CH3 O 2 6 . R R-O-R . :O CH3=> 7. 2 7 .. sp 3 => 8. 2 8 . 9. 2 9 . NH OH .=> 10. 2 10 . . . .=> 11. H+ _ 2 11 O BHHBH3 THF=> 12. 2 12 : : : . :CH3CH2 O CH2CH3diethyl ether orethyl etherCH3CH3 O CCH3CH3t-butyl methyl ether ormethyl t-butyl ether => 13. 2 13IUPAC :CH3CH3 O CCH3CH32-methyl-2-methoxypropaneO CH3Methoxycyclohexane=> 14. CH3H 2 _K+CH2CH2CH3 + Br14 + ( ) CH3 O HCH3CH3+ K CH3 OCH3CH3CH3 O_CH3+ CH3CH2 CHCH3Br CH3 OCH3_=> 15. 2 H15 -RO-H .CH3CH2CH CH21) Hg(OAc)2, CH3OH2) NaBH4CH3CH2CH CH2OCH3=> 16. CH3CH2 O H + H O CH2CH3 CH3CH2 O CH2CH3 2 16 . .=>H2SO4140C 17. 2 17 . . : HI > HBr >> HCl=> 18. ._ + CH3 O CH3 . 2 _18 HCH3 O CH3 H Br CH3 O CH3_ Br++BrHBr CH3 + H O CH3 . 19. 2 19 . :O CH2CH3HBrOH+ CH3CH2 Br=> 20. 2 20 . . : . . 21. HO H OH_O H 2 21 H2O, Cl2H HH Cl_H ClOH H=> 22. HO HHO H 2 22 . . . HBr HI HOHH+, H2OHOHHOHH+, CH3OHHOCH3 23. 2 23 .=> 24. 2 24 1.2 - . 1.2 - . . . 25. CH3CH2OH_OHC CH2CH3OCH OCH2CH3 2CH3H3C OHHC CH2H OCH2CH3 2 OCH2CH325 .OHHC CH2CH3OHC CH2CH3 .=>H3C OHHC CH2OCH2CH3+CH3CH2OHH+OHC CH2CH3 26. 2 26 27. 2 28. 2 28 . (OH) . sp 3 29. . OH : . OH : OH : . . OH:( ( 2 29 30. CH3OHOH 2 30: CH3CH3 CHCH2OH CH3 CCH3OHCH3 CHCH2CH3 => 31. 2 31IUPAC OH . ol alkane e- . OH . . 32. OH 2 32 :CH3CH3 CHCH2OHCH3CH3 COHCH3CH3 CHCH2CH32-methyl-1-propanol2-methyl-2-propanol2-butanolOHBr CH33-bromo-3-methylcyclohexanol=> 33. 2 33 => 34. OH 2 34 . . :CH3CH3 CHCH2OH CH3 CHCH2CH3isobutyl alcohol sec-butyl alcohol=> 35. 2 35 . . 37. 2 37 . 41. ( ( -OH - - 2 41 49. HH3CC OCH3CH3 2 49 + .CH3CH3CH3 CH CH2 CH2 CMgBrCH3CH3H3C CH2 C MgBrH HC OH3CCH3 CHCH2 CH2 CO HCH3HOH=> 50. OH CH2OH 2 50 CH3CH2CHCH2CH2CH3OHCH3OHCCH3 =>CH2CH3 51. 2 51 . . . 52. H3CR MgBr R C OMgBrR O MgBr C 2 52( ( 1 . !!C OCH3OCH3OCH3CH3COCH3CH3RO+ MgBrOCH3 53. CH3R MgBr + CR O MgBrCH3R OH 2 53 . .CROCH3RHOHCR=> 54. .OH 2 54... OHCH3CH2CCH3CH3CH3COHCH3CH2CHCH2CH3=> 55. 2 55 OH,NH,SH,-C-C-H . . C=N,C-N,S=O,N=O. => 56. 2 56 . . , NaBH4 , LiAlH4 => 57. H O 2 H O H57 -H . . .HCOHCHCHH3O+=> 58. 2 58 . .COOCH3H O HCH3O H + LAH => 59. LiAlH 4 . LiAlH 4 . 2 59 60. 2 60 . .OH2, Raney NiOHNaBH4OH=> 61. 2 61 62. 2 62 63. 2 633 2 1 64. 2 64 .Na2Cr2O7/H2SO 4H2CrO 4 : OHCH3CHCH2CH3Na2Cr2O7 / H2SO4OCH3CCH2CH3=> 65. OH N H CrO3Cl 2 O65 . . (PCC) PCC .CH3CH2CH2CH2CH3CH2CH2CH=> 66. 2 66 3 . .=> 67. 2 67 Cr2O : 3 : ) )KMnO4 ( )( )CUO 300 : . 68. HOC R X 2 68 .ROH .-RO . O-H C-O 69. 2 69 -OH .+H ( ) () .CHO + C-Nuc C-O 70. CH OO S O 2 CO O70

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