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2007 1 2

6 6 6 10 16 17 26 26 28 30 34 38 41 45 48 53 56 59 61 64 75 75 76 77 79 80 82 3

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122 124 126 128 128 131 132 133 136 138 140 142 144 144 148 157 5

1 2 3 4 5 6 6

1 2 3 4 5 6 1 1 2 7

(a) (b) (c) (d) 119 2. 1 2 3 4 5 3., 8

1 2 5% 3 1% 1% 4 4. HF 1 2 3 4 5. 50 Hz 200 V 1 ma 10 ma 25 ma 1 2 9

3 4 5 6 : 1-1 10

1-1 1 11

10 12 14 16 19 24 29 34 40 10 12 14 16 19 24 29 34 40 /mm 10 12.5 14.5 16 18.5 24 29.2 34.5 40 10/30 10 10mm 30 30mm 2 1-2 12

1-2 3 1 2 3 4 5 6 13

1-3 1-4 1-5 1-6 1-7 1-8 14

1-9 1-10 1-11 15

1/2 2/3 16

= / 100% 1.. 3. 1993 13600 17

2... 1982 600 3. Aldrich Catalog Handbook of Fine Chemicals. 2005 Aldrich 2005 41000 Aldrich http:// www. sigmaaldrich.com/local/ SA_Splash.html 4. Stecher PG. The Merck Index, 11th Ed.1989 Merck, 1, ( ),,,, (Name Reactions),,, Merck CA 12 13 (http://scistore.cambridge soft.com/software/product.cfm?pid=36) 5. Handbook of Chemistry and Physics Lide DR (Chemical Rubber Company) 18

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 http://www.hbcpnetbase.com/ 6. Heilbron I. Dictionary of Organic Compounds. 6th Ed.1995 1934 1 1 6 Merck Index 10 ( ) CA 2 7. Beilstein Handbuch der Organischen Chemie Beilstein Beilstein 19

Beilstein 1984 Beilstein Beilstein Beilstein Online Beilstein 1862 20 1 1881-1882 1885-1889 1906 80000 1918 31 1-27 28-29 30-31 31 (Hauptwerk) H 27 1910 20 Erganzungswerk E 1928-1938 1910-1919 27 1941-1955 1920-1929 29 1958 1930-1949 1950 1972 1950-1959 17 27 1930-1959 1984 1960-1979 17 20 4877 Beilstein 20

Beilstein Beilstein I-IV CA V CA C H O N Cl Br I F S P Ag Zr Ag Zr Beilstein 1. Organic Synthesis Adams R Gilman H Blatt A H 1921 1 2005 81 Notes Collective Volume 1-30 2. Organic Reactions Adams R 1942 2005 65 21

3. Reagents for Organic Synthesis Fieser LF Fieser M 1 1967 1966 2 1969 1969 1 2004 22 4. Synthetic Method of Organic Chemistry Theilheimer 1 1942-1944 Theilheimer s Method of Organic Chemistry 1 1999 55 5... 2, 1994 5 1 2 3 4 5 6... 3, 2000 6 1 2 3 4 5 6 7. Fieser LF, Williamson KL. Organic Experiments. D C Heath and Company, 1983 1935 1941 2 1955 3 1957 3 1964 Organic Experiments Wittig 3 8. Vogel s Textbook of Practical Organic Chemistry, 5th ed, Longman London, 1989 22

2 1 2 1. Scientia Sinica 1951 1951-1966 1973-1972 7 B C 2. 1950 3. 1933 (Journal of the Chinese Chemical Society) 1952 2004 4. Chinese Journal of Chemistry 1983 1989 1990 "Chinese Journal of Chemistry 2001 2005 1 1 Chinese Journal of Chemistry 23

Wiley-VCH Chinese Journal of Chemistry Wiley 5. 1964 () 1980 1983 1985 6. Chemical Research in Chinese Universities 1984 2004 7. Chinese Chemical Letters 1990 7 8. 1980 9. 1934 10. 1986 24

(Chemical Abstracts) CA 1907 160 60 17000 70 98 % CA 1967 67 CA 1 2 CA CA CA ( ) ( 26 ) ( 10 5 ) (keyword index)(author index)(patent index)(subject index) (general subject index) (chemical substance index) (formula index)(index of ring system)(registry number index) (parent compound index)(index guide) (CAS source index) CA ( ) () ( ) ( ) 1969 1996 CA on CD 1967 25

( ) 26

NaOH 1 2 100 155 3 4 27

1 2 3 4 10 28

. 1 80 2 80 200 2cm 3 100 ~250 20 29

4 250 ~350 5 1 0 5 2 3 4 5-38 30

300 0.5 2-1A 2-1B 2-1A 2-1B 2-1C M T melting point mp A B C 2-1 1 Thiele 1 Thiele 31

2-2 2-2 Thiele Thiele b Thiele Thiele Thiele 2 1mm 60mm~70mm 3 0.1g 0.2g 2mm 3mm 4 4 /min 5 /min 10 1 /min 1.5 /min 32

30 Thiele 2 1 Thiele 3mm 2 9cm, 3cm 0.9mm~1.1mm 3 80 80 4 5 10 1.0 ~1.5 2-3 2-3 33

1 2 3 2-4 2-4 1.0 ~1.5 1 2 Thiele 3 4 5 34

( ) 101.3kPa 760mmHg 1.33kPa(10mmHg) 0.5 10 101.3kPa(760mmHg) 100 101.3kPa 100 12.3kPa 92.5mmHg 50 50 /12.3kPa ( 30 ) 35

1 ~2 101.3kPa 760mmHg 1 2-5 2-5 2cm 36

140 140 2 1 2 ( ) [ ] 2-5 250mL 110mL 2~3 1~2 60mL 20C 2 V 2 /C 1 V 1 100% 37

4h [ ] 70 C 1 20 C 2 20 [ ] (1)?? 100 (2) 2 3 1 3 (3)?? (4) 1 2 / (5) (liquid) P A = P 0 A X liquid A P B = P 0 B X liquid B A B P A B P = P A + PB P 0 A, B0 liquid A B x liquid (gas) A x B 38

x gas A = PA P + P A B x gas B = PB P + P A B B x x gas B liquid B = PB P + P A B P P 0 B B = x liquid B 1 + x liquid A P P o A 0 B + liquid gas liquid 0 0 x A xb = 1 P A = P x B B liquid = 1 x A B B gas 0 0 P B > P x A B liquid > 1 x B 0 B ( P > 0 A P B )B ( ) ( ) 39

2-6 2-7 ( ) ( ) 2-6 2 ~3 1 1 2 3 [ ] l00ml 25mL 25mL 2-6 40

1 65 10mL (A) 80 ~85 (B) 85 ~100 (C) 100 ~115 (D) 115 ~125 (E) 115 ~125 2-8 4h 2-8 1:1 [ ] (1) (2)? (3)? (4)?? (5)? 41

1 2 2-9 - 181 20mmHg 1 B 181 C 20mmHg A 20mmHg 82 2-9 3 logp = A+B/T P T A B logp 1/T A B 2-10 ( ) 42

1 2 2-10 1 A C 1mm~2mm D 2 2mmHg~4mmHg 3 2-11 - - 43

2-12 2-13 2-11 2-12 2-13 2-10 1/3~1/2 D C G M 2/3 20 ~30 1~2 / D U 44

[ ] 2-10 20mL [ ] 6 ~8 0.93 kpa ~1.07kPa 30 4.2kPa [ ] 1 2 3 4? 100 100 1.33kPa P P A P B P=P A +P B P P 100 45

m A = m B M M A B P P A B M A P A 184.4 98.4 5.73 kpa 94.8 kpa 93 18 93 5.73/18 94.8=1/3.3 3.3g 1g 23% 135 95.5 86.1 kpa 15.2 kpa 6.5/1 61% 100 1.33 kpa 0.13 kpa ~0.67kPa 1% 100 2-14 A C 3/4 B A 46

2-14 500mL D 1/3 45 E F 30 E 5mm H T T G D G D D D D G D A B 2-15 2-16 47

2-15 ( ) 2-16 2-17 100 T 2-17 A B C 48

1 2 3 4 5 6 0.1g 1mL 0.5mL/ 4mL 1mL 4mL 49

1 20% 2 1%~5% 5 ~10 3 3-1 50

(a) (b) 2-18 2-18a 2-18b 2-19 2 3 4 1 3 5 2-19a 2 5 6 1 4 7 2-19b 2 4 8 1 5 9 2-19c 2-19d 1 9 9 5 8 2 2-19e 2-19f 1 2 2-19g 51

2-19 4 2 5 2-20 2-20 52

1 ~2 6 20 [ ] 2g 250mL 70mL 0.1g 5min ~10min 150mL 5mL~10mL 1 ~2 114 g/100ml 0.46(20 ) 0.84(50 ) 3.45(80 ) 5.5(100 ) [ ] 1 2 3 4 53

5 6 7 8 9 X A X X A B B A B X A B X A = K( ) X B V 1 W 0 XV B B W 1 X A X A B W1 0 W1 W V1 WB W1 V1 K W0 W1 V B = K W KV 1 1 = W0 W 2 X A 1 B KV + V 54

W 2 V W 1 W 1 2 V B = K W 2 KV1 = W1 KV1 + VB KV1 = W0 KV1 + VB 2 Wn W n KV1 n = W0 1 B KV + V KV 1 ( B) KV1 + V 1 n Wn 100mL 4g 15 100mL K 1/3 100m 75 1 100mL = 4g 3 1 100mL + 100mL 3 W1 = 1.0g 100mL 3 33.3mL 3 1 100mL = 4g 3 1 100mL + 33.3mL 3 W3 = 87.5% 1 2-21 0.5g 55

2 3 2 3 3 5 2-21 2 Soxhlet 2-22 2-22 56

V V n V n = V 2-23 A B N A n sinα n sinα B = A N=1 n = sin β N sin β n D 5893Åt 1 3.5 10-4 ~5.5 10-4 Abbe Abbe 1 A B A B n A <n B =90 sin =1 0 t D 57

0 n = 1 sin β 0 0 Abbe 2-24 2 Abbe 2-25 Abbe 1.3000~1.7000 2-26 Abbe 2-25 Abbe 2-26 Abbe 58

3 Abbe 1 Abbe 1 ~2 :1. 33299 n 20 D 2 2~3 3 4 Abbe 1 Abbe 2 3 4 dl 59

2-27 2-27 [ ] t α [ α] λ = cl t α λ α lρ [ α ] t t λ D t l dm c 1mL [ ] = 60

1 5 15min, 2 3 4 5 e.e 100% [ α] D = [ α] D 100% e.e e.e% (S-R)/(S+R) 100% S R (-) X% (-) [X (100 X)/2]% (+) [(100 X)/2] % 61

1 CaCl 2 + 6 H 2 O CaCl 2.6H 2 O 2 1 2 Na + 2 H 2 O 2 NaOH + H 2 Na 2 SO 4 10H 2 O 1g Na 2 SO 4 1.27g 1.27 25 255.98Pa CaCl 2 6H 2 O 0.97 25 39.99 1 62

1 ~1.5 100mL CaCl 2 6H 2 O, 0.97 1g 0.97g 1g 1g 7 g ~10g 10mL 0.5g ~1g 3 2-1 CaCl 2 nh 2 O 0.97 n=1,2,4,6 CaCl 2 6H 2 O 1.05 MgSO 4 H 2 O MgSO 4 CaCl 2, n=1,2,4,5,6,7 7H 2 O CaCl 2 Na 2 SO 4 10H 2 O 1.25 2 CaSO 4 H 2 O 0.06 K 2 CO 3 H 2 O 0.2 63

( ) Na + H 2 O NaOH + H 2 CaO + H 2 O Ca(OH) 2 P 2 O 5 + 3H 2 O 2H 3 PO 4 0.25 1. 2. 3. N 2 O 2 H 2 Cl 2 NH 3 CO 2 CO 2 H 2 O 64

2-2 2-2 CaO NaOH KOH NH 3 H 2 HCl N 2 O 2 CO 2 SO 2 P 2 O 5 H 2 N 2 O 2 CO 2 SO 2 H 2 HCl N 2 O 2 CO 2 SO 2 ( ) : (thin layer chromatography) TLC (Rf) R f = 1 65

1 H G HF 254 254nm GF 254 2 G GF 254 HF 254 2 (0.25mm~lmm) 1 2 3g 6mL~7mL0.5 ~1 3g 7.5 2.5cm 5~6 3 105 ~ll0 30min 200 4h 150 ~160 4h - 2-1 2-1 66

% 0 3 6 10 15 % 0 5 15 25 38 4 lcm ( ) 1 lmm 1cm~1.5cm 2mm 5 Rf ( ) < < < < < < < < < < < < < < < < < 15 ( 2-28) 45~60 ( 2-29) R f 2-28 2-29 67

6 1 R f 2 GF 254 254nm ( ) 2-30 1 3 ph 4 ph 7.5 ph 10 68

100-150 2 >>>>> > 3 4 5 1 0.5cm 3/4 0.5cm 69

3/4 2 3 ( ) 2-31 70

2-31 2-32 1 3cm 20cm,5cm 30cm 8cm 50cm 2 1 N,N- 2 3-4 5 / =4:1:5 3 1% 71

0.2cm 0.5cm 4 1cm 5 6R f (Rf) R f = R f R f (5mg 500mg) (Gas Chromatography) GC 500 GLC GSC - 1 - - 72

3mm, 1m 10m 2 2-33 1 30mL/min ~120mL/min 2 2mm~6mm 1m~3m 0.25mm~0.75mm, 3 73

2-33 high pressure liquid chromatography high performance liquid chromatography HPLC 1 30 5~50 100kg/cm 2 2 2-34 3 1 2 74

2mm~5mm 25cm 2-34 75

1. 2. OH H 2 SO 4 + H 2O 50 15 g (15.6 ml 0.15 mol) 1 ml 90 lh 3 ml~4 ml 5% 1 g~2 g 80 ~85 6 g~8 g 82.98 n 20 D 1.4465 3h 4h 76

( 70.8 l0 ) ( 64.9 30.5 ) ( 97.8 80 ) 1. 2. 3. (1)3- -l- (2)3- - - (3)3,3- -2-1. 2. (CH 3 ) 3 COH HCl (CH 3 ) 3 CCl H 2 O 125 ml 9.5 ml(7.4 g 0.1 mol) 25 ml 5 min 5% 77

48 52 7 g 52 n 20 D 1.3877 3h 4h 25 5% 1. 2. Sandmeyer Sandmeyer 0-5 Sandmeyer 2 CuSO 4 2 NaCl NaHSO 3 2 NaOH 2 CuCl 2 Na 2 SO 4 NaHSO 4 H 2 O 78

CH 3 CH 3 CH 3 CH 3 NaNO 2 HCl Cl CuCl HCl CuCl 2 + N 2 NH 2 N N N N Cl 1 3.5 g 0.034 mol 2.3 g (0.0575 mol) 25 ml 250 ml 15 g(0.06 mol)cuso 4 5H 2 O 4.5g(0.077mol) 50 ml 60 70 50 ml 25 ml 2 100 ml 5.4 g(0.05 mol) 15 ml 15 ml 5 3.8 g(0.055 mol) 10 ml 5 85% 90%- 5 min 3-15 min 50 60 N 2 500 ml 80 ml 10 ml 10% 5 ml 158 162 3 g 3.5 g 162 n 20 D 1.5150 6h 8h 5 79

- 1. 2. 3. 4. 2- -2-1. Grignard Grignard 2. Grignard n Et + Mg 2 O C 4 H 9 Br n C 4 H 9 MgBr CH 3 n C 4 H 9 MgBr + CH 3 COCH 3 Et 2 O n C 4 H 9 C CH 3 OMgBr CH 3 CH 3 n C 4 H 9 C CH 3 NH 4 Cl, H 2 O n C 4 H 9 C CH 3 OMgBr OH 250 ml CaCl 2 2.4 g(0.1 mol) 15 ml 13.7 g(0.1 mol) 80

30 min 7.4 ml(0.1 mol) 10 ml 30 min 20% 50 ml 60 ml 20 ml 30 ml15% 139 143, 50% 2- -2-143 n 20 D 1.4175 6h 8h 1. 2. 3. 4. 1. Grignard Grignard 2. Grignard Reagent PhBr + Mg Et 2 O PhMgBr 81

PhCO 2 C 2 H 5 + 2 PhMgBr Et 2 O Ph 3 COMgBr PhCOPh + PhMgBr Et 2 O Ph 3 COMgBr Ph 3 COMgBr NH 4 Cl, H 2 O Ph 3 COH 1 250 ml CaCl 2 0.75 g 3.4 ml 5 g 0.032 mol 13 ml - 0.5h 2 1.9 ml(2 g,0.013 mol) 5 ml 0.5h 3.8 g 14 ml 70% 2.3 g 2.5 g 161 162 162.5 6h 8h 0.75 g 3.2 ml(4.8 g 0.03 mol) 15 ml 5.5 g(0.03 mol) 15 ml 0.5h6 g 22 ml 70% 2 g 2.3 g 161 162 82

6h 8h 1. 2. 3. 4. 1. 2. 1 mol 4 mol PhCOPh + NaBH 4 Na + [B(OCHPh 2 ) 4 ] - Na + [B(OCHPh 2 ) 4 ] - H 2 O 4 Ph 2 CHOH PhCOPh Zn + NaOH Ph 2 CHOH 50 ml 1.82 g (0.01 mol) 20 ml 95% 83

0.4 g (0.01 mol) 50 20 min 40 ml 10% 3.5 ml~5.0 ml 30~60 1 g 69 3h 4h 50 ml 1.5 g 1.5 g 1.5 g 15mL 95% 20 min 80 5 min 80 ml ph 5~6 30~60 69 3h 4h 10g 1mL 1. 2. 10% 84

1. 2. Grignard CH 3 CH 2 OH + H 2 SO 4 CH 3 CH 2 OSO 2 OH + H 2 O 140~150 CH 3 CH 2 OSO 2 OH + CH 3 CH 2 OH CH 3 CH 2 OCH 2 CH 3 + H 2 SO 4 150 ml 13 ml 95% 12.5 ml 0.5 cm 1 cm ( ) 25 ml 95% 140 ( 1 2 ) 140 150 30 min 40 min 10 min 160 250 ml 8 ml 5% 8 ml 8 ml 1 g 2 g, 100 ml 50 60 33 38 35 4h 85

: 1.? 2.? 3.?? (CH 3 ) 3 COH CH 3 OH 15%H 2SO 4 + (CH 3 ) 3 COCH 3 150 ml 35 ml 15% 8 ml(0.2 mol) 10 ml(0.11 mol) 49 53 25 ml 15 ml 5% 15 ml 15 ml 100 ml 53 56 55.2 4h 86

? N 2 Cl NO 2 NO 2 NaNO 2 HSO 4 H 2 SO 4 NO 2 NH 2 H 2 SO 4 N N OH 1 200 ml 11 ml 18 ml 7 g(0.051 mol) 25 g 0 5 3.5 g(0.051 mol) 10 ml 5 5 min 10 min 1-10 min 2 500 ml 25 ml 33 ml 15 min 4 g 5 g 15% 87

50mL 3 g 96 4h 6h 1. 2. 1. - 2. Friedel-Crafts Friedel-Crafts AlCl + (CH 3 CO) 2 O 3 COCH 3 + CH 3 COOH 250 ml ( ) 18 g, 22 ml(0.247 mol) 8 ml(0.071 mol) 88

30 min 50 60 ( 40 min) 25 ml 50 ml 15 ml 20 ml 20 ml 5% 202 6h 1.? 2.? 12 min O OH C CH Cu (OAc) 2 or HNO 3 O O C C 89

50 ml 10 ml 5mL 5 g(0.04 mol) 2.1 g(0.01 mol) 45 min 25 ml 95% 1.5 g 93 94 95 3h 4h 50 ml 2.1 g(0.01 mol) 7 ml 0.15 mol 100 10 min 12 min 30 ml 95% 1.5 g 94 95 3h 4h 1. 2. 90

-H PhCH 3 + 2KMnO 4 PhCO 2 K + MnO 2 + H 2 O PhCO 2 K + HCl PhCO 2 H + KCl 250 ml 3.6 ml(0.034 mol) 150 ml 11.4 g(0.072 mol) 1.5h 2h MnO 2 ph 2 3 2 g 124 122.4 3h 4h 1 ml 2 ml 100mL 0.18 g 4 0.27 g 18 2.2 g 75 91

- CH 3 CO 2 H Na 2 Cr 2 O 7 H 2 SO 4 NO 2 NO 2 250 ml 6 g(0.044 mol) 18 g(0.065 mol) 20 ml 30 ml 30 min 1h 60 g 20 ml 30 ml 5% 30 ml 30 ml 10% 60 20 ml 30 g ph,, 242 242 4h 6h 92

? 1. 12- -9- ( ) 2. 1010 + KOH 95% CH3 (CH 2 ) 5 CH(OH)CH 2 CH CH(CH 2 ) 7 COOH CH 3 (CH 2 ) 5 CH(OH)CH 2 CH CH(CH 2 ) 7 COOH KMnO 4 HO 2 C(CH 2 ) 7 CO 2 H 1 250 ml 5 g 50 ml 95% 23 g 2h 150 ml 50 ml 12- -9- ( ) 20 g 2 15 g 0.05 mol 12- -9- ( ) 100 ml 4 g 1000 ml 39 g 300 ml 12- -9- ( ) 0.5h 14 ml 1.84 25 g 50 ml 120 15 min 150 ml 200 ml 30 ml 3 g 97 104 106.5 93

8h 1:3 40 1. 2. 12- -9- ( ) - (benzilic acid) - - - Ph O C O C Ph KOH C 2 H 5 OH, H 2 O Ph OH OH C CO 2 K H 3O + Ph C CO 2 H Ph Ph 94

25 ml 3 ml 1.3 g 0.0023 mol 4 ml 95% 1.3 g(0.006 mol) 15 min 10 ml 10 min ph=2 0.7 g 3 1-148 149 150 4h 1. 2. Perkin, - CH + (CH 3 CO) 2 O 3 COOK HCl PhCHO PhCH CHCO 2 H K 2 CO 3 + CH 3 CO 2 H 95

50 ml 3.4 ml(0.033 mol) 5 ml (0.052 mol) 2 g 1.5h 500 ml 5 g 6 g ph=8 9, ( 10 ml) (ph=2 3), 2.7 g 3:1 133 4h 6h 50 ml 3 ml(0.03 mol) 8 ml(0.084 mol) 4.2 g 0.5h 20 ml 500 ml 10% 20 ml 3 g 4h 135.6 1. 2. 3. 96

-3-1. (Knoevenagel) 2. 1,2- -2- Knoevenagel Knoevenagel -3- NaOH -3- CHO OH + CH 2 (CO 2 C 2 H 5 ) 2 NH O CO 2 C 2 H 5 O + C 2 H 5 OH O CO 2 C 2 H 5 O i. KOH ii. HCl O CO 2 H O 1-3- 50 ml 2 ml(2.3 g,0.0019 mol) 3.2 ml(3.3 g, 0.0021 mol) 12 ml 0.2 ml 2h 14 ml 50% 1mL 3 g 92 93 25% -3-93 2. -3-50 ml -3-2 g 0.009 mol 1.5 g 0.0027 mol 95% 10 ml 5 ml 15 min 5 ml 25 ml 97

1.5 g m.p.188 189 ( ) -3-190 6h 8h -3- Williamson Williamson PhOH + NaOH PhONa + H 2 O 2 ClCH 2 CO 2 H + Na 2 CO 3 2 ClCH 2 CO 2 Na + CO 2 PhONa + ClCH 2 CO 2 Na PhOCH 2 CO 2 Na + NaCl PhOCH 2 CO 2 Na + HCl PhOCH 2 CO 2 H + NaCl 1. 250 ml 5.6 g 0.060 mol 60 ml 35% ph 12 45 50 2. 98

250 ml 6.2 g (0.066 mol) 10 ml 15% 4 g 40 ph ph 7 8 3. 100 110 2h 11 ml ph=1 2 20 ml 20% 10 ml ph=1 2 98.5 4h, ph 12 50 40 1.?? 2.,? 1. 2. 99

2,4- FeCl OCH 2 CO 2 H + HCl/H 2 O 3 2 Cl OCH 2 CO 2 H 50 ml 3.0 g 10 ml 55 10 mg FeCl 3 10 ml HCl 60~70 10 min 3 ml 33% H 2 O 2 20 min 1:3 158~159 4h HCl H 2 O 2 Cl 2 Cl 2 2 3mL 1. Cannizzaro 2. - 50% 100

2C 6 H 5 CHO + KOH C 6 H 5 CH 2 OH + C 6 H 5 COOK H + C 6 H 5 COOH 125 ml 18 g(0.32 mol) 18 ml 20 ml(21 g 0.2 mol) 24h 20 ml 3 5 ml 10 ml 10% 10 ml 204 206 8 g 205.35 n 20 D 1.5396 ph=2 3 1 2 8 g 9 g 122.4 6h 8h 1. Cannizzaro 2. Cannizzaro - 101

2 CHO + NaOH O O CH 2 OH + O CO 2 Na H + O CO 2 H 11 ml(0.133 mol) 100 ml 5.4 g(0.133 mol) 50 ml 8 ml 10 15 0.5h 1h 13 ml 15 ml 3 3 g 169 172 3.5 g 5.5 g 171 n 20 D 1.4868 ph=2 3 10 ml 1 2 5 g 133 134 6h 8h (a) 15 10 (b) (c) 102

1. 2. 3. 4. 5. 6. ph=2 3 1. 2. B PABA B 10 PABA (CH 3 CO) 2 O p-ch 3 C 6 H 4 NH 2 p-ch 3 C 6 H 4 NHCOCH 3 CH 3 CO 2 Na + CH 3 COOH p-ch 2 KMnO 4 2MnO 2 + KOH 3 C 6 H 4 NHCOCH p-ch 3 CONHC 6 H 4 CO 2 K 3 + + p-ch 3 CONHC 6 H 4 CO 2 K + H 3 O + p-ch 3 CONHC 6 H 4 CO 2 H 103

p-ch 3 CONHC 6 H 4 CO 2 H 1 + H 2 O p-nh 2 C 6 H 4 CO 2 H + CH 3 CO 2 H 500 ml 7.5 g 0.07 mol175 ml 7.5 ml 12 g 20mL 50 8 ml(0.085 mol) 7.5 g 154 2 600 ml 7.5 g 20 g(0.08 mol) 350 ml 85 20.5 g(0.13 mol) 70 ml 30 min 85 15 min 2mL 3mL 20% 5 g 6 g 3 5 ml 18% 250 ml 30 min 30 ml 10% 30 ml 1 ml 173 6h 8h 104

1. 2. 3. 4. 1. 2. H 2 SO 4 CH 3 CO 2 H + CH 3 CH 2 OH CH 3 CO 2 CH 2 CH 3 + H 2 O 100 ml 14.3 ml 23 ml 7.5 ml 0.5h ph 10 ml 10 ml 50 ml 73 78 10 g 12 g 105

77.06 n 20 D 1.3727 4h 6h 17mL 1mL 30 min / /% 70.2 82.6 8.4 9.0 70.4 91.9 8.1 71.8 69.0 31.0 1. 2. 3. 1. 2. 106

CO 2 H CO 2 C 2 H 5 + C 2 H 5 OH H 2 SO 4 + H 2 O 50 ml 4 g 0.033 mol 99.5% 10 ml 0.17 mol 8 ml 1.5 ml 2h 3h 1.5 ml 30 ml CO 2 ph 7 10 ml 210 213 213 n 20 D 1.5001 4h 6h 50 ml 4 g 0.033 mol 99.5% 10 ml 0.17 mol 1.5 ml 2h 4h 6h 0.6 g 64.8 74.1% 18.5% 7.4% 84% 86.0% 12.7% 1.3% 16% 4.8% 52.1% 43.1% 1.5 ml 1. 107

2. 1. 2. CO 2 H CO 2 H CO 2 - NH 4 + CO 2 H Sn HCl NH 3 -H 2 O CH 3 CO 2 H NO 2 NH 2.HCl NH 2 NH 2 CO 2 C 2 H 5 C 2 H 5 OH H 2 SO 4 Na 2 CO 3 NH 2.H 2 SO 4 CO 2 C 2 H 5 NH 2 1. 100 ml 4 g 0.02 mol 9 g(0.08 mol) 20 ml(0.25 mol) 20 min 30 min 250 ml 4 ml ph 7 8 2. 100 ml 2 g 0.015 mol 20 ml 0.34 mol 2.5 ml 0.045 mol 1 h 1.5 h 85mL 250 ml 10% 108

1 g 2 g 92 10h 12h,, 1. 2. 10%? 1. 2. 3. - - 2 CH 3 CO 2 C 2 H 5 Na C 2 H 5 OH [CH 3 COCHCO 2 C 2 H 5 ] - Na + H 3 O + CH 3 COCH 2 CO 2 C 2 H 5 100 ml 2.5 g 0.11 mol 20 ml 28 ml 109

50% ph=5 6 5 ml 6 g 180.4 /mmhg* 760 80 60 40 30 20 18 14 12 10 5 1.0 0.1 / 181 100 97 92 88 82 78 74 71 67.3 54 28.5 5 * 1mmHg= 1 Torr = 133.322Pa 6h 8h 50% 1. 2. 1. 2. 110

() PhNH 2 + CH 3 CO 2 H PhNHCOCH 3 + H 2 O 100 119 25 ml 5 ml 0.055 mol 7.5 ml(0.13 mol) ( 0.1 g) 15 min 100 100 110 1.5h 100 ml 5 g 114.3 3h 4h 2mL ( ) 111

Beckmann OH Na 2 Cr 2 O 7 H 2 SO 4 O O + NH 2 OH N OH + H 2 O N OH (1)85%H 2 SO 4 (2)20%NH 3 -H 2 O O NH 1. 250 ml 10.5 ml 10.1 g 0.1 mol 55 55 60 0.5h 0.5h 60 ml 15 ml 20 ml 50 ml 12 g 15 ml 151 155 6 g 7 g 155.6 2. 250 ml 5 g 0.07 mol 7 g 15 ml 35 40 5.2 ml 5 g 0.05 mol 2 min 3 min 5.5 g 89 90 90 112

3. 500 ml 5 g 0.044 mol 10 ml 85% 120 160 250 ml 0 5 20% 20 ph 60 ml 1h 25mL 127 133 /0.93 kpa(7 mmhg) 137 140 /1.6 kpa(12 mmhg) 140 144 /1.86 kpa(14 mmhg) 2 g 8h 10h 500 ml 10.5 g 60 ml 9 ml 30 95 38.4% 31 2.4 g 1. 2. 20% NaOH 113

Na 2 S + NaHCO 3 NaHS + Na 2 CO 3 NO 2 NO 2 + + + 4 6NaHS H 2 O 4 3Na 2 S 2 O 3 NO 2 NH 2 125 ml 6 g 0.025 mol 12.5 ml 2.1 g 0.025 mol 15 ml 20 15 min 10 ml 100 ml 2.5 g 0.015 mol 20 ml 20 min 80 ml 1.5 g 75% 1 g 114 4h 1. 2. 114

TEBA PhCH 2 Cl (CH 3 CH 2 ) 3 N ClCH 2CH 2 Cl (CH 3 CH 2 ) 3 NCH 2 Ph Cl 100 ml 5.5 ml(0.05 mol) 7 ml(0.05 mol) 20 ml 1,2-1.5h 1,2-10 g 3h 4h Friedel-Crafts Fe (CH 3 CO) 2 O H 3 PO 4 Fe COCH 3 (CH 3 CO) 2 O H 3 PO 4 Fe COCH 3 COCH 3 115

100 ml 1 g 0.0054 mol 10 ml 10.8 g,0.10 mol 2 ml 85% 15 min 40 g 500 ml 10 ml 15 min 50 ml 60 90 4h 6h B 1 - B 1 2 CHO VB 1 O C OH CH 50 ml 0.9 g(0.0034 mol) B 1 2 ml 7 ml 95% 2.5 ml 10%10 min ph=9 10 5 ml 5.2 g 0.05 mol 116

67 75 1.5h 20 ml 3 g 95% 2 g 134 136 137 4h B 1 1g 6mL95% 1. 2. ph 9 10 ph 1. 2. (ph < 3.0) N,N- 117

N,N- H 2 N SO 3 H NaNO 2 - O 3 S N + N - O 3 S N + N + N(CH 3 ) 2 1 OH - H 2 O (CH 3 ) 2 N N N SO 3 Na 100 ml 1.0 g(0.005 mol) 0.4 g(0.0055 mol)nano 2 15 ml 5 min 2 0.7 ml (0.0055 mol) N,N- 15 min 2.5 ml 10%NaOH 35 ml 1 g 1.5 g NaOH 4h N,N- 1. 2. 118

8-8- 8-8- -1,2-8- OH NH 2 + CH 2 OH CHOH CH 2 OH H 2 SO 4 NO 2 OH N OH 100 ml 9.5 g 7.5 ml,0.1 mol 1.8 g 0.013 mol 2.8 g 0.025 mol 4.5 ml 1.5h 2h 6 g 6 ml 8-200 ml 250 ml 3 g 25 ml - 4:1 8-2 g 2.5 g 8-75 76 8h 0.5% d=1.26g/cm 3 8-180 100 119

8- ph 7 8 8-8- 8-1. 2. Skraup - 4- -3- -2- - -, - Claisen-Schmidt CHO + O O 25mL 2.1mL 4.0mL 4.0mL 3.0 ml 2.5mol/L 25 30 1 2h 1:1 bp120 130 /0.93kPa(7mmHg) 140 /2.13kPa(16mmHg) 2.00g 66.7% mp38 39 120

1.? 2. 4- -2-4- -2-4- -2-4- -2- CH 3 COCH 2 COOC 2 H 5 CH 3 ONa [CH3 COCHCO 2 C 2 H 5 ] - Na + C 6H 5 CH 2 Cl CH3 COCHCO 2 C 2 H 5 CH 2 C 6 H 5 NaOH, H 2 O CH 3 COCHCO 2 - Na + CH 2 C 6 H 5 H + CH 3 COCH 2 CH 2 C 6 H 5 50 ml 4.5 ml 5.3 g 3.0 ml 10 min 2.7 ml 30min 1.20 g 10 ml 5 min ph 11 30 min 40 3.0 ml ph=1 2 30 min 10 ml 121

ph=6 7 132 140 /5.35 kpa(40 mmhg) 1.70 2.10 g 48% 59% Friedel-Crafts ( ) AlCl 3 Lewis HX Friedel-Crafts Ar H + R X AlCl 3 Ar R + HX Ar H + R COX AlCl 3 Ar CO R + HX AlCl 3 AlCl 3 Ar H + R CO 2 O AlCl 3 Ar CO R + RCOOH O O O OH + O AlCl 3 + HCl O 2.5 g 122

15 ml 6 g A1C1 3 1 5 A1Cl 3 30 35 HCl A1C1 3 ( 10 min) 1h 10 g 12 ml 15 ml 10% Na 2 CO 3 10 min 5mL 60 127 93 95 2-1. 2. C C N 4-(1- ) O + HN O O N + H 2 O 4-(1- ) 2- O N + CH 3 COCl O N COCH 3 H 2 O HCl O COCH 3 1 4-(1- ) 10mL 2.1 g 2.6 g 5 50 ml 10mL 3h 2.7 g 70% 4-(1- ) 123

2 2-50 ml 2.3 g4-(1- ) 1.6 g 19mL 1.2 g 5.5 ml 0 0 0 1h 50 ml 20 ml 3h 10mL ph5 6 78 81 /16kPa 0.12g 63% 4-(1- ) 97 101 /0.99 1.07kPa n 23.5 D=1.5120 2 3 1. 2. 3. 4. 124

1. 2. 1848 louis Pasteur ( ) ( ) ( ) [ α] ( op ) = 100% [ α] (-)- 125

(-)- (+)- (α) [α](op) (-)- H H CH 3 NHCH 3 OH C 6 H 5 1 (-)- 50 ml 4 g l0 ml 1 g 5 ml (-)- l0 ml l00 ml (-)- 2 (-)- 30 ml 3 g l0 ml 1.5h 2h 40 ml 2.2 g 165 20 ml (-)- (-)- 1.5 g 169 170 l0 ml ( l ml) l0 ml (-)- 0.5 g 131 132 126

(-)- (-)- 20 ml l0 ml (+)- 3 (+)- (-)- 2 [α]= 156 8h 216 ~ 220 [α] 25 D= -33 ~ -35.5 (-)- (+)- (-)- 1.? 2. α= -6-6 +354? 127

OCH 2 CH 2 2,2,7,7,12,12,17,17-Octamethyl-21,22,23,24-tetraoxaquaterene O 4 + 4CH 3 C O CH 3 HCl CH 3 CH 3 O CH 3 CH 3 O O O CH 3 CH 3 CH 3 CH 3 α-c 95 5 () 1 95 80 1.? O C CH 3 CH 3 + 2. 128

C C C C R C CH R C C R 0.1%KMnO 4 H 2 SO 4 1:5v/v 2 0.1% KMnO 4 4 H 2 SO 4 10 129

5%Br 2 CCl 4 10 1 ~2 Br 2 CCl 4 5 1 * 0.1%KMnO 4 H 2 SO 4 1:5v/v 1 0.1%KMnO 4 10 H 2 SO 4 2 * CaC 2 +2H 2 O HC CH +Ca(OH) 2 +Q 5g~6g 1 10 2 0.1%KMnO 4 H 2 SO 4 1:5v/v 1 0.1%KMnO 4 10 H 2 SO 4 130

3 5%AgNO 3 5%NaOH 5%NH 4 OH 3mL Ag C C Ag+2HNO 3 2AgNO 3 +HC CH * 5 5%AgNO 3 1 5%NaOH 5%NH 4 OH AgNO 3 +NaOH AgOH+NaNO 3 2AgOH Ag 2 O +H 2 O Ag 2 O+4NH 4 OH 2[Ag(NH 3 ) 2 ]OH+3H 2 O Tollen's reagent Ag 3 N 4 5 * 3.5gCuSO 4 5H 2 O 1gNaCl 12mL 1gNaHSO 3 10mL 5%NaOH 10mL~15mL 2CuSO 4 +NaCl+NaHSO 3 +H 2 O Cu 2 Cl 2 + NaHSO 4 Cu 2 Cl 2 +4NH 4 OH Cu 2 (NH 3 ) 4 Cl 2 +4H 2 O 2.5mL 1mL H 2 SO 4 1mL H 2 SO 4 3 4 2 2 Br 2 CCl 4 131

Br 2 CCl 4 3mL H 2 SO 4 9mL 3g 15mL 10% NaOH 150 160 170 C CO CO 2 SO 2 SO 2 NaOH 140 150 160 160 170 4 0.1%KMnO 4 H 2 SO 4 1:5v/v 1 0.1%KMnO 4 5 H 2 SO 4 1 * KMnO 4 132

Br 2 CCl 4 5 5 Br 2 CCl 4 HBr (1) (2) C-X X OH NH 2 CN R-I > R-Br > R-Cl RCH=CHCH 2 X PhCH 2 X > R-X > RCH=CHX Ph-X 1-1- 1- AgNO 3 0.5mL AgNO 3 2 ~3 1-1- 1-1- AgNO 3 3 1mL 5 1-5min 1 * RCOX RCH CHCH 2 X ArCH 2 X R 3 CCl RI RCH 2 Cl R 2 CHCl 2,4-133

ArX RCH CHX HCCl 3 (1) RI > RBr > RCl PhCH 2 Cl CH 3 (CH 2 ) 2 Cl PhCl (2) CH 3 CH 2 Br CH 2 CHBr 1 2 3 10 * Lucas ZnCl 2 /HCl 3 Lucas 8 26 ~27 1mL Lucas * 1 134

> > 10min~15min Lucas 2 Lucas 34g 27g HCl 5%CuSO 4 5%NaOH 5 5%CuSO 4 10 5%NaOH Cu(OH) 2 5 * 0.1% KMnO 4 5% NaOH H 2 SO 4 1 5%NaOH 3 H 2 SO 4 5 0.1%KMnO 4 5 * 1% 3 1% * 2,4,6-1%1% 1% 1% 1%FeCl 3 135

5 1 1%FeCl 3 * 1 FeCl 3 2 6C 6 H 5 OH FeCl 3 [Fe(C 6 H 5 )O 6 ] 3-6H + 3Cl - 5%FeCl 3 5 5%FeCl 3 3 ~4 *FeCl 3 FeCl 3 OH O + 2 FeCl + + 3 2 FeCl 2 2 HCl OH O OH O O H O + OH O O H O H 2 SO 4 10%KI 10%KI 5 1mL 1 H 2 SO 4 5 1 1 136

CuSO 4 5H 2 O 1 2 3 4 RCHO RCOR C=O NaHSO 3 10 NaHSO 3 3 * 100mL 40%NaHSO 3 25mL 2,4-5 2,4-1 *2,4-1g2,4-7.5mL H 2 SO 4 75mL 95% 250mL 5%NaOH 4 3 10 5%NaOH 50 ~60 137

* 1 CH 3 CO CH 3 CH(OH)R 2 2g 5g 100mL Fehling I II 5 2 * 1 Cu 2 O HCHO + Cu 2 O Cu + HCO 2 H Cu 2 O 2 Fehling I 34.6g CuSO 4 5H 2 O 500mL II 173g 70gNaOH 500mL 5%AgNO 3 5%NaOH 5%NH 4 OH 1 2mL 5% AgNO 3 1 5% NaOH 5% NH 4 OH Tollen s reagent 2 2 ~3 * schiff 2 2 138

* 1 Schiff s reagent 2 0.2g 120mL 20mL 1:10 2mL 200mL 0.1g SO 2 SO 2 SO 2 1 2 CO 2 H ph ph5 ph3 H 2 SO 4 1mL 1mL 2 H 2 SO 4 10min 2mL 139

H 2 SO 4 1:5v/v 5%NaOH 2%FeCl 3 10 5 1 H 2 SO 4 60 ~70 5% NaOH NaOH ph 2 5%FeCl 3 *FeCl 3 2 (CH 3 COO) 3 Fe [Fe 3 (OH) 2 (CH 3 COO) 6 ] + Cl - + 2CH 3 COONa + FeCl 3 + 2H 2 O H 2 O + 2NaCl + 2CH 3 COOH Fe(CH 3 COO) 2 OH 2,4-0.5mL 2,4-1 1 0.5mL 1 1 2 1%FeCl 3 0.5mL 1 1 1%FeCl 3 * FeCl 3 140

3 1%FeCl 3 1 1mL 1%FeCl 3 1 * 1 7.5% 2 FeCl 3 FeCl 3 FeCl 3 1 2? NH 3 NH 2 20%NaOH 1mL 5 3 3 4 20%NaOH * 2mL~3mL 1 1mL 141

* 2,4,6 N-N,N- 10%NaOH N-N,N- 10%NaOH10 2 1 2 N- 3 N,N- *N,N- N-N,N- HCl 5%NaOH 5%NaNO 2-1 2 0.5mL 6 HCl 0 5%NaNO 2 3 2-2 N- 2 N-0.5mL 3 HCl 5%NaNO 2 5 3 2 N,N-3 HCl 5%NaNO 2 3 -N,N- 5%NaOH -N,N- * 1 3 142

Ar N + N Cl - HCl NaOH NaOH Ar N + N OH - HCl Ar N N OH NaOH HCl Ar N N ONa N N OH + NH 2 N N NH 2 + H 2 O 2 NO NO 2 3-4g - 40mL5%NaOH 1 2 2% 2% I II 2% 2% 5 I II 5 143

2% 2% 5%AgNO 3 5%NaOH 5% 1mL 5% AgNO 3 5%NaOH 5% 5 60 ~80 2% 2% 2% 2% 2% 2% 0.5mL 0.1g 30min * 2:3 144

1 34.51 n 20 D 1.3526 2~3 1mL2% 1~2 FeSO 4.H 2 O 60g 100mL 6mL 100mL 10mL 250mL 100mL 10mL 34.5 70 80mL (!) 1g 24h 2 145

78.5 n 20 D 1.3611 98%~99% 1 64.9 68.3 2 100mL95% 20g 3h~5h 99% 1 100mL99% 7g 27.5g 25g 2~3h 2 60mL99% 5g 0.5g 900mL99% 5h 99.9% 3 56.2 n 20 D 1.3588 250mL 100mL 0.5g 1h 250mL (!) 55.0 56.5 4 77.06 n 20 D 1.3723 95%~98% 5 1h 77 1000mL 100mL 10 4h 20g~30g 99% 5 146

30 60 60 90 90 120 150mL 100mL 10mL 10 lh 6 40 n 20 D 1.4242 5% 40 ~41 7 61.7 n 20 D 1.4459 1 ( ) 5 6 24h 60.5 61.5 8 76.8 n 20 D 1.4603 4% 1000mL 60g 60mL 100mL 50 ~60 30min 76.7 9 80.1 n 20 D 1.5011( 15 ) 10 24h 79.5 80.5 10 110.6 n 20 D 1.4969 147

30 11 64.96 n 20 D 1.3288 0.02% 0.1% 0.5%~1% 99.9% 64 12 67 (64.5 ) n 20 D 1.4050 1000mL 2~4g 66 13 101.5 12 n 20 D 1.4424 500mL 8mL 50mL 6~10h 24h 8h~12h 1,4-14 115.5 n 20 D 1.5095 15 DMSO 189 18.5 n 20 D 1.4783 76 /1600Pa(12mmHg) 90 148

16 N,N- DMF 149 ~156 n 20 D 1.4305 N,N- N,N- 76 /4800Pa(36mmHg) 1/10 80 N,N- N,N- 2,4 17 46.25 n 20 D 1.6319 55 ~65 0.5% 2.5% 149

n 20 D 150

/ / 20 n D C 14 H 12 O 2 212.244 1.310 20 137 344, 194 12 (-)- C 10 H 15 NO 165.232 1.0085 22 40 225 1,2- C 2 H 4 Cl 2 98.959 1.2454 25-35.7 83.5 1.4422 25 12- -9- ( ) C 18 H 34 O 3 298.461 0.9450 21 227 10 1.4716 21 2- -2- C 7 H 16 O 116.201 0.8119 20 143 1.4175 20 2- C 7 H 10 O 2 126.153 1.0431 25 72-5 20 1.4906 20 4- -2- C 10 H 12 O 148.201 0.9849 22-13 233.5 1.511 22 4- -3- -2- C 10 H 10 O 146.185 1.0097 45 41.5 261 1.5836 45 8- C 9 H 7 NO 145.158 1.034 20 75.5 267 N,N- C 6 H 5 N(CH 3 ) 2 121.08 0.9557 2.45 194.15 1.5582 N,N- C 8 H 11 N 121.180 0.9557 20 2.42 194.15 1.5582 20 α- C 10 H 7 OH 144.19 1.0989 96 288 1.6224 β- C 10 H 7 OH 144.19 1.28 123 124 295 1 C 6 H 6 78.12 0.87865 5.5 80.1 1.5011 0. C 6 H 5 NH 2 93.13 1.02173-6.3 184.13 1.5863 3 151

C 6 H 6 O 94.111 1.0545 45 40.89 181.87 1.5408 41 C 7 H 8 O 108.138 1.0419 24-15.4 205.31 1.5396 20 C 7 H 6 O 106.122 1.0401-57.1 178.8 1.5463 C 7 H 6 O 2 122.12 1.2659 15 122.35 249.2 1.5040 132 C 9 H 10 O 2 150.174 1.0415 25-34 212 1.5007 20 C 8 H 8 O 3 152.148 98.5 285 C 6 H 5 COCH 3 120.16 1.0281 20.5 202.0 1.53718 C 6 H 5 CH=CH 2 104.16 0.9060-30.63 145.2 1.5468 C 7 H 12 O 4 160.168 1.0551 20-50 200 1.4139 20 ( ) HOCH 2 CHOHCH 2 OH 92.11 1.2613 20 290 1.4746 CH 3 CH 2 COOH 74.08 0.9930-20.8 140.99 1.3869 CH 3 COCH 3 58.08 0.7899-95.35 56.2 1.3588 CH 3 CH=CH 2 42.08 0.5193( ) -185.25-47.4 1.3567-70 (C 6 H 10 O 5 )n (162.14)n CH 3 (CH 2 ) 2 CH 2 OH 74.12 0.8098-89.53 117.25 1.39931 C 6 H 7 NO 3 S 173.191 1.485 25 288 C 7 H 7 NO 2 137.137 1.51 25 173 C 9 H 11 NO 2 165.189 1.717 20 92 310 1.5600 22 152

C 7 H 8 O 3 S 172.203 104.5 140 20 C 7 H 9 N 107.153 0.9619 20 43.6 200.4 1.5534 45 C 9 H 11 NO 149.189 1.2120 15 152 307 C 8 H 7 O 3 Cl 186.592 156.5 C 7 H 7 Cl 126.584 1.0697 20 7.5 162.4 1.5150 20 C 7 H 5 NO 4 167.120 1.610 20 242 C 7 H 7 NO 2 137.137 1.1038 75 51.63 283.3 C 14 H 10 O 2 210.228 1.084 102 94.87 347 C 13 H 12 O 184.233 69 298 C 13 H 10 O 182.217 47.9 305.4 1.6077 19 C 14 H 12 O 3 228.243 150 180 C 14 H 10 O 2 210.228 1.084 102 94.87 347 (CH 3 ) 2 NH 45.09 0.6804(0 ) -93 7.4 1.350(17 ) C 4 H 4 O 68.08 0.9514-85.65 31.36 1.4214 C 4 H 4 O 68.074 0.9514 20-85.61 31.5 1.4214 20 C 5 H 6 O 2 98.101 1.1296-14.6 171 1.4869 C 5 H 4 O 2 96.085 1.1594-38.1 161.7 1.5261 C 5 H 4 O 3 112.084 133.5 231 153

C 6 H 12 O 100.16 0.9624 25.15 161.1 1.4641 3 C 6 H 10 O 98.15 0.9478-16.4 155.65 1.4507 C 6 H 11 NO 113.157 90 206 C 6 H 12 84.16 0.77855 6.55 80.74 1.42662 C 6 H 10 82.143 0.8110 20-103.5 82.98 1.4465 20 C 5 H 8 O 84.117 0.9487 20-51.90 130.57 1.4366 20 CH 3 (CH 2 ) 5 OH 102.18 0.8136-46.7 158 1.4078 0 C 6 H 11 NO 113.157 69.3 270 CH 3 (CH 2 ) 4 CO 2 H 116.16 0.9274 205.4 1.4163 1. CH 3 (CH 2 ) 4 CH 3 86.18 0.6603-95 68.95 1.37506 C 6 H 5 CH 3 92.15 0.8669-95 110.6 1.4961 C 7 H 8 92.139 0.8668 20-94.95 110.63 1.4961 20 CH 3 OH 32.04 0.7914-93.9 64.96 1.3288 C 14 H 14 N 3 O 3 SNa 327.34 C 5 H 12 O 88.148 0.7353 25-108.6 55.2 1.3690 20 HCOOH 46.03 1.220 8.4 100.7 1.3714 CH 4 16.04 0.5547 0-182.48-164 3 C 6 H 4 (OH) 2 110.11 1.2717 178 154

C 6 H 4 N 2 O 4 168.107 1.5751 18 90 291 C 6 H 6 NO 2 138.124 0.9015 25 114 306 C 6 H 5 NO 3 139.109 1.2797 100 96.8 194 70 C 8 H 8 O 3 152.148 1.2890 20 C 6 H 7 NO 109.126 1.328 25 174 153 C 8 H 4 O 3 148.116 1.527 4 130.8 295 C 7 H 8 O 2 124.138 1.1613 25 87 C 7 H 6 O 2 122.122 1.1674 20-7 197 1.5740 20 C 6 H 5 NO 3 139.109 1.2942 40 44.8 216 1.5723 50 C 2 H 6 O 4 S 126.133 1.3657 20 280dec 1.4105 20 C 7 H 7 Cl 126.584 1.004 20-45 179 1.5391 20 C 2 H 3 O 2 Cl 94.497 1.4043 40 63 189.3 1.4351 55 CH 3 CH 2 Cl 64.52 0.8978-136.4 12.37 1.3673 0 CH 2 =CHCl 62.50 0.9106-153.8-13.37 1.3700 C 4 H 9 NO 87.120 1.0005 20-4.8 128 1.4548 20 CO(NH 2 ) 2 60.06 1.3230 135 1.484 1.602 1 C 5 H 11 N 85.148 0.8606 20-11.02 106.22 1.4530 20 C 9 H 16 O 4 188.221 1.225 25 106.5 287 100 1.4303 111 155

C 9 H 8 O 2 148.159 1.2475 4 133 300 C 19 H 16 O 260.329 1.199 0 164.2 380 C 6 H 15 N 101.190 0.7275 20-114.7 89 1.4010 20 (CH 3 ) 3 COH 74.12 0.7887 25.5 82.2 1.3878 C 4 H 9 Cl 92.567 0.8420 20-25.60 50.9 1.3857 20 C 7 H 6 O 2 122.122 1.1674 20-7 197 1.5740 20 C 6 H 5 NO 2 123.11 1.2037 5.7 210.8 1.5562 0. C 6 H 5 Br 157.02 1.4950-30.8 156 1.5597 C 6 H 5 Br 157.008 1.4950 20-30.72 156.06 1.5597 20 CH 3 CH 2 OH 46.07 0.7893-117.3 78.5 1.3611 CH 3 CN 41.05 0.7857-45.72 81.6 1.34423 C 4 H 10 O 74.121 0.7138 20-116.2 34.5 1.3526 20 CH 3 CHO 44.05 0.7834(18 ) -123.37 20.1 1.3316 CH CH 26.04 0.6208(-82 ) 80.8 84.0( ) 1.00051( ) CH 3 COOH 60.05 1.0492 16.604 117.9 1.3716 (CH 3 CO) 2 O 102.09 1.0820-73 1 139.55 1.39006 12( CH 3 COOC 2 H 5 88.12 0.9003-83.578 77.06 1.3723 CH 3 CH 3 30.72 0.572(-108 ) -183.3-88.63 1.03769 CH 2 =CH 2 28.05 1.260-169.15-18l( ) -103.71 1.363,(-100 ) 156

C 6 H 5 NHCOCH 3 135.17 1.2190(15 ) 114.3 304 0.53( CH 3 COCl 78.50 1.1051-112 50.9 1.38976 CH 3 COOC 6 H 4 -COOH 180.17 135( ) CH 3 COCH 2 CO 2 CH 2 CH 3 130.141 1.0368 10-45 180.8 1.4171 (CH 3 ) 2 CHOH 60.11 0.7855-89.5 82.4 1.3776 (CH 3 ) 2 CHCH 2 OH 74.12 0.7982-108 108 1.3939 (CH 3 ) 2 (CH 2 ) 2 CH 2 OH 88.15 0.8092-117.2 128.5 1.4053 C 4 H 9 Br 137.018 1.2758 20-112.6 101.6 1.4401 20 CH 3 CH 2 CHOHCH 3 74.12 (25 ) 0.8063-114.7 99.5 25 1.3978 12 C 14 H 13 O 3 229 150 180 ( ) C 10 H 15 NO 165.232 1.1220 20 76.5 135 12 (-) C 10 H 15 NO 165.232 1.0085 22 40 225 C 7 H 7 Cl 126.584 1.1004 20-45 179 1.5391 25 C 14 H 10 O 3 226 199 CHCl 3 119.377 1.4788 25-63.34 61.17 1.4459 20-3- C 10 H 6 O 4 190 190 157

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