有机化合物的构造构型和构象sf

1、会计学1有机化合物的构造构型和构象有机化合物的构造构型和构象sfCH3CH2CH2CH3CH3CHCH3CH3CH3CH3CH3CHOCHOCH3CH2CH2CH3CH3CHCH3CH3CH3CH3CH3CHOCHOCH3CH2CH2CH3CH3CHCH3CH3CH3CH3CH3CHOCHOCH3CH3CH3CH3BrCOOHBrCOOHOOCH3CH3CH3CH3BrCOOHBrCOOHOOCH3CH3CH3CH3BrCOOHBrCOOHOOCH3OCH3CH3CH2OHCH3CH2CHO CH3COCH3CH3CH2COOHCH3COOCH3CH3COCl ClCH2CHOCH3OCH3C

2、H3CH2OHCH3CH2CHO CH3COCH3CH3CH2COOHCH3COOCH3CH3COCl ClCH2CHOCH3OCH3CH3CH2OHCH3CH2CHO CH3COCH3CH3CH2COOHCH3COOCH3CH3COCl ClCH2CHOCH3OCH3CH3CH2OHCH3CH2CHO CH3COCH3CH3CH2COOHCH3COOCH3CH3COCl ClCH2CHOCH3CCH2COOEtOCH3CCCOOEtOHHCH3CCH2CCH3OOCH3CCCOCH3OHH酮式烯醇式酮式烯醇式构型CCAABBCCABBACCCCHCH3CH3HCH3CH3HHbp()mp()

3、41-139-105CCCCHCH3CH3HCH3CH3HHbp()mp()41-139-105HCOOHHOOCH井冈山风景桂林风情生活中的对映体镜象左右手互为镜象左右手互为镜象生活中的对映体镜象同分异构构造异构 立体异构碳链（骨架）异构官能团位置异构官能团异构互变异构构象异构构型异构顺反异构光学异构CH3CH2CH2CH3CH3CHCH3CH3CH3CH3CH3CHOCHOCH3CH3CH3CH3BrCOOHBrCOOHOOCH3OCH3CH3CH2OHCH3CH2CHO CH3COCH3CH3CH2COOHCH3COOCH3CH3COCl ClCH2CHOCH3CCH2COOEtOCH3

4、CCCOOEtOHHCH3CCH2CCH3OOCH3CCCOCH3OHH酮式烯醇式酮式烯醇式CH3CH3CH3CH3BrCOOHBrCOOHOOHCOOHHOOCHCCAABBCCABBACOHHOOCCH3HCCOOHCH3OHHCCOOHHOCH3HCCOOHCH3HOH(S)- (S)- (R)- (R)-COHHOOCCH3HCCOOHCH3OHHCCOOHHOCH3HCCOOHCH3HOH(S)- (S)- (R)- (R)-CCHClClHCClClHCH3COOHHOHHOHCOOHHFHClClHHFCH2CH2CH2CH2ClClNHHH C3CH3CH3C2CH3CH3HH

5、HHC2COOHCOOHHOHHOHC2（无） （有） （无） （有）化学性质：仅在手性环境下表现出差别 旋光性：对偏振光的作用不同 CCOOHCH3OHHCCOOHCH3HOHS-(+)-乳酸R-(-)-乳酸CCOOHCH3OHHCCOOHCH3HOHS-(+)-乳酸R-(-)-乳酸HCOOHHOOCHHCOOHHOOCHHCOOHHOOCHHCOOHHOOCHCCOOHH3CHOHCCOOHCH3HHOHOHCOOHCH3（前）（前）（后）（后）交叉点 手性碳（位于纸平面上）投影式的转换规则1.不能离开纸面翻转。翻转180。，变成其对映体。2.在纸面上转动90。, 270 。，变成其对映体

6、。3.在纸面上转动180。构型不变。4.保持1个基团固定，而把其它三个基团顺时针或逆时针地调换位置，构型不变。5. 任意两个基团调换偶数次，构型不变。6. 任意两个基团调换奇数次，构型改变。投影式的辅助规则（不是必需的）1 1 碳链写在竖键上，其它原子或基团写在横键上碳链写在竖键上，其它原子或基团写在横键上2 2 编号小的碳原子写在竖键上端编号小的碳原子写在竖键上端口诀口诀竖向后，横向前，含碳原子上下连。竖向后，横向前，含碳原子上下连。转半圈，不能翻，编号小者在上端。转半圈，不能翻，编号小者在上端。偶次互换是原物，奇次互换构型变。偶次互换是原物，奇次互换构型变。COHHOOCCH3HCCOOH

7、CH3OHHCCOOHHOCH3HCCOOHCH3HOH(S)- (S)- (R)- (R)-基团大小顺序：OH COOH CH3 H S投影式：小基团在竖键上，顺时针为R型，逆时针为S型， 小基团在横键上顺时针为S型，逆时针为R型，CH3CHOCH2CH3HCH3CHOCH2CH3HCCH2CH3HOCH3H SRRCH3CHCOOHOH*CNH2COOHHCH3CHCOOHOH*CNH2COOHHCCOOHCH3OHHCCOOHCH3HOHS-(+)-乳酸R-(-)-乳酸D20= +3.8o(水) D20= -3.8o(水)HOOC-CH-CH-COOH*OH ClC-2: -OH CHC

8、OOH COOH HC-3: Cl COOH CHCOOH HClOHHOHClHCOOHCOOHCOOHHOHHClCOOHHOHHClCOOHCOOHHOHClHCOOHCOOH 2R3R 2S3S 2R3S 2S3R dl-dl-HOHClHCOOHCOOHCOOHHOHHClCOOHHOHHClCOOHCOOHHOHClHCOOHCOOH 2R3R 2S3S 2R3S 2S3R dl-dl-HOOC-CH-CH-COOHOH OH* 酒 石 酸 OH COOH CHCOOH HOH *C2 *C3 ：HOHHOHCOOHCOOHHOHHOHCOOHCOOHHOHHOHCOOHCOOHH

9、OHHOHCOOHCOOHHOHHOHCOOHCOOHHOHHOHCOOHCOOHHOHHOHCOOHCOOHHOHHOHCOOHCOOHCCCABABsp2spC=C=CClHClH（有手性）H H1,2-丁二烯HHCH3ClHCOOHHHOOCHCOOHHOOCHCOOHHHHOOC螺环型和环与双键相连的化合物。NO2HOOCCOOHO2NO2NHOOCCOOHNO2O2NHOOCClClOHOHN+C6H5 OH-CH3CH3CH2CH2C6H5P+C6H5CH2CH2CH3CH3 Br-CH2C6H5HCOOHHOOCHHCOOHHOOCHHCOOHHOOCHHCOOHHOOCHHCO

10、OHHOOCHHCOOHHOOCHHCOOHHOOCHHCOOHHOOCHHCOOHHOOCHHCOOHHOOCHHCOOHHOOCHHCOOHHOOCH1，2 顺式内消旋反式外消旋1，2写单环化合物的立体异构体时，可将环看作平面来对待，思路：先顺反后判断再照镜BrClClBr顺顺RSRSRSBrClClBr反反RSBrCl当两个取代基不同时：反 式外 消 旋顺 式内 消 旋反 式1， 21， 21， 3顺 式1， 3BrClRSClBrClSRBrRSClClSRBrBr1，2 顺式内消旋1，3 顺式内消旋反式外消旋1，2反式外消旋1，31，2 顺式内消旋反式外消旋1，2反式外消旋1，31，

11、3 顺式内消旋反式1，4顺式1，4CCOOHCH3OHHCCOOHCH3HOHS-(+)-乳酸R-(-)-乳酸CCOOHCH3OHHCCOOHCH3HOHS-(+)-乳酸R-(-)-乳酸HCOOHHOOCHHCOOHHOOCHHCOOHHOOCHHCOOHHOOCHCOHHOOCCH3HCCOOHCH3OHHCCOOHHOCH3HCCOOHCH3HOH(S)- (S)- (R)- (R)-基团大小顺序：OH COOH CH3 H S （1） ClOHHCH3BrBrBrBrHHHHBrHHBr(2)(3)CH3OH(4)PhPhClHH H（1） ClOHHCH3BrBrBrBrHHHHBrH

12、HBr(2)(3)CH3OH(4)PhPhClHH H（1） ClOHHCH3BrBrBrBrHHHHBrHHBr(2)(3)CH3OH(4)PhPhClHH H123456123456CH2231564CH2CH2CH2231564TC = twist chairB = boatTB = twist boatC = chairTC = twist chairB = boatTB = twist boatC = chair123456654321531246612345123456CH2HRCH2HR123456CH2CH2234561 R 键（） -CH3 95 -CH(CH3)2 97 -

13、C(CH3)3 99.99 1，3 顺式内消旋反式外消旋1，3反式1，4顺式1，412121212CH3CH(CH3)21212121212CH3CH(CH3)22131313131ClBr31313131ClBr(1) ClCl(2) CH3CHCHCHCHCH3CH2(3) ClCl(4) CHOHOCH3CH3OCH3HCl(5)(6)(7)(8)薄荷醇CCH3CH3CCCCCH3CH3HHOHHOHCH3HCH3OHOHHHCH3HOHOHCH3HCH3HOHOHCH3(A)(B)(C)CH3CH3BrHOHHHBrHOHHH(6) CCHOCH3HHCH3OHCCCH3OHHOHHC

14、H3(7) CH3CH3NH2HOHHNH2HHH3COHH3C(8) HCH3CH3HCH3HHCH3(9) CH3CH3CH3CH3(10) ClClHHClHClH(5)CH3CH3BrHOHHHBrHOHHH(6) CCHOCH3HHCH3OHCCCH3OHHOHHCH3(7) CH3CH3NH2HOHHNH2HHH3COHH3C(8) HCH3CH3HCH3HHCH3(9) CH3CH3CH3CH3(10) ClClHHClHClH(5)CH3CH3BrHOHHHBrHOHHH(6) CCHOCH3HHCH3OHCCCH3OHHOHHCH3(7) CH3CH3NH2HOHHNH2HH

15、H3COHH3C(8) HCH3CH3HCH3HHCH3(9) CH3CH3CH3CH3(10) ClClHHClHClH(5)CH3CH3BrHOHHHBrHOHHH(6) CCHOCH3HHCH3OHCCCH3OHHOHHCH3(7) CH3CH3NH2HOHHNH2HHH3COHH3C(8) HCH3CH3HCH3HHCH3(9) CH3CH3CH3CH3(10) ClClHHClHClH(5)(1) COOHCOOHBr(2) NO2COOHNO2HOOC(3) CH3CHCC(CH3)2(4) C6H5CHCCHC6H5(5) O(6) CH3CH3CHCH3 CH3CHBrCH3H

16、HCH3HHHHH Br BrClClClCH3CH3Cl CH3 CH3 CH3ClClClClHHHCHBr ( ) ( ) ( ) ( ) 2R3R,2S , 3S2R ,3r, 4S2R , 3s ,4SA B C D1C H C lC lC HH232O HB rHC H33HHHC lC lC l4(C H ) C HCCHHCHC H23 25HC HC HHC lC l336C H SHHHC lC HB r37HHC lO H8HC H31CH ClClCHH232OHBrHCH33HHHClClCl4(CH ) CHCCHHCHCH23 25HCHCHHClCl336CH

17、SHHHClCHBr37HHClOH8HCH31CH ClClCHH232OHBrHCH33HHHClClCl4(CH ) CHCCHHCHCH23 25HCHCHHClCl336CH SHHHClCHBr37HHClOH8HCH31CH ClClCHH232OHBrHCH33HHHClClCl4(CH ) CHCCHHCHCH23 25HCHCHHClCl336CH SHHHClCHBr37HHClOH8HCH31CH ClClCHH232OHBrHCH33HHHClClCl4(CH ) CHCCHHCHCH23 25HCHCHHClCl336CH SHHHClCHBr37HHClOH8HC

18、H31CH ClClCHH232OHBrHCH33HHHClClCl4(CH ) CHCCHHCHCH23 25HCHCHHClCl336CH SHHHClCHBr37HHClOH8HCH31CH ClClCHH232OHB rHCH33HHHClClCl4(CH ) CHCCHHCHCH23 25HCHCHHClCl336CH SHHHClCHB r37HHClOH8HCH31ClCH32OHOH34HHOHOHCHCH3356OHCH37C HHCCCHCHCCHHCH2 523H58CH39CH3OHOHHHCH3CH3CH3CH3BrCOOHBrCOOHOOCH3CH3CH3CH3BrCOOHBrCOOHOOCH3CH3CH3CH3BrCOOHBrCOOHOO左右手互为镜象左右手互为镜象生活中的对映体镜象HOOC-CH-CH-COOHOH OH* 酒 石 酸 OH C