有机化学①

1. CH3HH2SO4H3O+(CH3)2CHCHCH(CH3)2 CCCH3 CH(CH3)2OH OONBSZn-HgAlCl3CH3CH+CH3CClCH3CH22. (1) CH3C浓HClBr

NaOHHg(OAc)2NaBH4 CH2CHCHOCHCH3CH乙醇 CH3CH3OH

NaOHCH3CHCH3CH H2OBrOH (2)

SCH3HCH3SNa HHSN2HCl3. (1) CH3CH3 HClSCH3CH3SNaKBrHH HDMSOSN2HBrHSN2 (2)

CH3CH3CH3 OOHCH3CH2CHCHCH3CH232C COCH2OHCCH2CHCH3 C: 3CH4. A: 3 B:

5.

(1) 2?甲基?4?氯戊烷

(5) (1S,2R,3R) ?1?甲基?2,3?二溴己烷 (7) 2,5?环己二烯?1?醇 (9) 4?苯基?1,6?庚二烯?4?醇 (11) 2,2?二甲基?3?戊炔?1?醇 6. (1)

H+Cl2hvClKOH乙醇NBS(2) 4?甲基?2?氟?3?氯?1?戊醇

(8) (1R,3R)?(2?甲基)?环己?1?醇 (10) (1R,2S)?1?甲基?2?氯环己烷 (12) 2?甲基?4?甲氧基?2?丁醇 Br( )CuLiCH2CHCHCH2(3) (2S,3R,4R)?3?甲基?2?氯?4?溴戊烷 (4) 1?溴甲基?2?氯?1?环戊烷 (6) 反?1?甲基?4?甲氧基环己烷或反?甲基?4?甲基环己基醚

CHCH3Cl( )CuLiCH2CHCHHBrRO2RCH2Br2CHCH2BrBr1. Li2. CuI???1. NaNH22. H2OCCHCHCHBr (2)

7. (1)

(2)

ClCHCHBr2NaNH2CCOHClKOH乙醇KMnO4OHOHPh(COOH)2H2OHg(OAc)2NaBH4(CH3)2CHOHB2H6H2O2/OH-OHOCH(CH3)2OHNaHONaCD3IOCD3

SClCH3O OCH3CH2CH2CH2CH2OS (3) ① CH3CH2CH2CH2CH2OH ON HBr(CH3)3COKCH3CH2CH2CHCH3CH3CH2CH2CHCH2

BrMgDO2 CH3CH2CH2CHCH3CH3CH2CH2CHCH3无水乙醚 DMgBr ② MgD2OHBrCH3CH2CH2CH2CH2OH无水乙醚K2Cr2O7OCH3

CH3MgIH3O+NaOHOHBrO (4) H2O 乙醚H+

NaHONaCH3CH2BrOCH2CH3

CH3CH3 CH3(CH3)2CCHCH3CH3

8. (1) (2) (3) (4) 9. (1)

OHH2SO4CH3OHH2SO4CH3CH3CH2CH2CH2CH2DOHCH3CH3HBrBrCH3CH3 (2)

BrCHCHO+CHCHCHOO10. (1) (2) 2 2 (3) 3

O

CH3HBrROOROCCH3OCCH3CHO (4) (5)

CH3CCHCH3OHBrCH3CH3CCH3CHO

11. CHCHNaNH2CHCNaCH3CH2BrCH3CHCCHNaNH2CH3CHCCNa22O H2OCH3CH2CCCH2CH2OHCH3CH2CCCH2CH2ONa

CH2CH2OHH2, Pd/C BaSO4CH3CH2 CCN、S化合物HH

12. (1) CH3CH2Br + CH CNa CH C–CH2CH3 CH3CH2CH=CH2

OHMgH2SO4CH3CHO H3O+CHCHCHCH323乙醚 (2) CH3CH2Br CH3CH2MgBr 过酸CH3CHCHCH3

O CH3CH=CHCH3 OHMgCH3CHOH3O+ CH3CH2CHCH3乙醚

O13. CH3CH2Br CH3CH2MgBr K2Cr2O7CHCHCHC323 H+

OHO

BrMgCCH2CH3MgBrCH3CH2CCH3H3O+Br2

FeCH3 OONaOCH2CH3 NaNH2CCH2CH3CH3CH2BrCCH2CH3

CH3CH2CHCH2OCH3CHOOHCH2OCHOHOHOHCH2ONaNH（3液）过酸CH3CH3，CH3CH3 CHCH2 OHH 3+OCHHCH2OCH 3CHO OHH+HO CH3CH2OCH3CHCH2HOHOCH3HCH2OCH3

CH3