TABLE II. ORGANIC DERIVATIVES OF ALKENES, CYCLOALKENES ...chemistry.gsu.edu/files/2014/11/Alkenes.pdf · table ii. organic derivatives of alkenes, cycloalkenes, dienes and polyenes

TABLE I I . O R G A N I C D E R I V A T I V E S OF A L K E N E S , CYCLOALKENES,D I E N E S A N D POLYENES

a) Liquids 1) (Listed in order of increasing b.p.* )**

No

1

2345

6

7

89

1011

1213

14

15

1617

181920

21

22

23

24

25

2627

Name

Erhene(Ethylene)Propene (Propylene)CyclopropeneAllene2-Methylpropene

1-Butene

1,3-Butadiene

lrani-2-Buteae.Cyclobuteneas 2-Butene1,2-Butadiene(Methyla l lene)

3-Methyl-l-butene1,4-Pentadiene

1-Pentene

2-Methyl-l-butene

3-Methylcyclobutene2-Methvl-l,3-

butadiene (Isoprene)

/rans-2-Pentenem-2-Pentene1-Methyl-l-oclo-butene

2-Methvl-2-butene

3-Methvl-l,2-bula-diene(l 1 Dimethyl-a l lene)

Cyclopentadiene

1,3-Penladiene(Piperylene)

3,3-Dimethyl-l-butene

1, lrart?-3-Pentadienel,«s-3-Pentadiene

Boilingpoint•c

-10371-47 70-36'"-345-690

-626

-441

0882 43721085

20062597

2997

31 16

323407

3635369437 1

38 57

40

4083 '

41 1

41 24

42034407

Meltingpoint

•c

-169 15T

-185 25T

-136-14035

-18535

-10892

-105 55

-13891-136 19

-16849-14828

-16522

-13756

-14595

-14024-151 39

-13377

-85

-889

-1152

-8747- 140 82

no

1 3467

1 3465

1 4292 '0650 '

1 4208'

1 36431 38876

1 37148

1 3778

1 40051 42194

1 37931 38301 4088

1 3874

1 410

1 4398 ' » 5

1 4309

1 3760

1 430081 43634

D;°

0 384"05139

0 5942s

05951

06255 '

0 6042s

0733°06306'0652s

062720 66706

0 64050

06504

0 68095

064820655607244

06623

0680

07983"

06803

06529

0 67603069102

Bromine addition product

x-Bromo-

dl-

dl-

telra-di-

d,-

telra-

di-

di-letra-

di-lelra

di-

di-

di-tetra-

di-di-

tetra-

tetra-

di-

etra-eira-

B P . ' C

131 36141 99

149

1663

161 0

161 0975

61 2"

68"

474 48"

90-6"15560'2

91 0™92 4™

150 21

95356'"

13IJ

13I J

M P / C

983-555

107

118 Igr

-2

855 60,eth

1 1 4 5 , a l

115,al115, al

"B

1 538681 52004

1 62001 5080

1 5150

1 5110

1 51101 6070

1 50932

1 5012"

1 5088

1 50961 5096

1 594"

1 5109

D;°

2 17921 93268

27031 7595

1 7951

1 7852

1 785225085

I 6776

1 592'»

1 6711

1 68091 6817

2 305"

1 5615

Miscellaneous

2,4 Dmitrophenyl-sulfenyl chloride.86 7

2.4-Dimtrophenyl-sulfenyl chloride.775 85

Mercaptosuccmicacid adduct.1073 6

Mercaptosuccmicacid adduct.1223-6

Maleicanh adduct.63-4, Igr

Nitrosochlonde, 74,Mercaptosuccmicacid adduct.1537-40

Dimer 32, Maleicanh adduct, 1645 Benzoqumoneadduct, 75 6

Maleic anh adduct.61, pet eth , OxidbyKMnO,-*HCOOH +CH,COOH

* Derivative data given in order m p , crystal color, solvent from which crystallized**T = triple point, S = at saturation pressure

12

TABLE I I . O R G A N I C D E R I V A T I V E S O F A L K E N E S , C Y C L O A L K E N E S ,DIENES AND POLYENES

a) Liquids 1) (Listed in order of increasing b.p.)* (Continued)

No

28

29

30

31

3233

3435

36

37

38

3940

4142434445

4647

48

4950

5152

5354

55

Name

Cyclopentene

1,2-Pentadiene(Ethylallene)

2,3-Pentadiene ( l 3-Dimethylallene)

4-Methyl-l-pentene

3-Methyl-l-pentene3-Methyl-l,4-pen(a-

diene2,3-Dimethyl-l-butene2-Methyl-l,4-pen(a-dicne

4-Methyl-m-2-pentene

4-Methyl-/ra«i-2-pentene

1,5-Hexadiene(Bia l ly l )

2-Methyl-l-pentene1-Hexene

2-Ethyl-l-butene/ranj-13-Hexadiene3-Methylcyclopentenem-3-Hexene3-Hexene (cis-lrans

mixture)rrani-3-Hexene2-Methyl-2-pentene

3-Methyl-/ra/)i-2-pentene

rro«5-2-Hexene2-Hcxene (cis-trans

mixture)2,3-Hexadiene2,3-Dimelhyl-M-butadiene

c«-2-Hexene4-Methyl-l,2-penta-

diene(l-Isopropyl-allene)

3-Methyl-cw-2-pentene

Boiling

point•c

4424

4486

4827

5388

54 1455

556756

563

58 55

5946

6076349

64 6645 55650664466 6-67

67086729

6763

6787679 8 1

686878

688470

7045

Meltingpoint

•c

-13508

-13726

-12526

-15363

-1530

-15727

-13443

-14081

-1408

-13572-13982

-131 53

-13782

-11343-1357

-13484

-13297

-7601

-141 14

-13845

"8

1 42246

1 42091

1 42842

1 3828

1 38421 405

1 39041 405

1 3880

1 3889

1 4042

1 39201 38788

1 39691 4060"1 42071 39471 3942

1 39431 4004

1 4016

1 39351 3928

1 395I 4394

1 39771 424

1 4045

DP

077199

0 69257

0 69502

06642

066750695

067790694

06690

06686

06923

06817067317

0689406925"076220679606816

0677206863

06942

0678406813

068007267

068690708

06986


x Bromo

dl-

letra-

di

di

di-

di

di-

lelra-

didi-

di-lelra-

didi-

di-di-

di-

di-di-

di-tetra-

di-

di-

B P 'C

71 5"

94 6" '

87"

99"'

80'

72 3'"

78"

87 8'°89 90'"

872 '

80 1 I J

80 \"

80 I 1 3

71-2"

72 4"

90'"9016

90'6

72-415

M P 'C

52

19

47, Igr138, bz

nb°

1 5MO"

1 4980

1 5060

1 5105

1 5060

1 5070

1 50151 5024

1 S I I 2

1 50451 5045

1 50451 5063

1 5085

1 50251 5025

1 5025

1 5085

D;°

1 8713"

2 3469 \:

1 5689

1 6016

1 6033

1 5983

1 5996

1 55811 5774

1 6045

1 60271 6027

1 60271 5849

1 58121 5812

1 5812

Miscellaneous

Mercaptosuccmicacidadduct142 8 3 1 Pseudo-mtrosite 69 70Perbenzoic acidoxid —epoxy-cyclopentaneb p 102 3

Mercaptosuccmicacid adduct1026 9

Oil HNO3-»suc-cmicac 185

2,4-Dimtrophenyl-sulfenyl chloride61 2 Mercapto-succmic acid ad-duct, 94 5 5 7

MercaptosucciTiicacid adduct,152 1 6

Maleic anh adduct.78-9

'Derivative data given in order m p , crystal color, solvent from which crystallized

13

TABLE II . O R G A N I C D E R I V A T I V E S OF ALKENES, CYCLOALKENES,DIENES AND POLYENES


No

56

57

58

59

6061626364

65

66

67

68

69

70

71

72

7374

75

76

77

78

79

Name

2-Methyl-2,3-penta-diene (Tnmethylallene)

1,4-Hexadiene

4,4-Dimethyl-l-pentene

1, (m and/or [rans)-3~hexadiene

2,3-Dimethvl-2-burene2-Ethyl-l,3-butadiene4-Methylcyclopentene1-Melhylcyclopentene

2-Methyl-l.k« and/orira/M)-3-pentadiene

1,2-Hexadiene(«-Propylallene)

2-Methyl-l,(c« and/or(rani )-3-pentadiene

4-,V1ethyl-l,3-penta-diene

4,4-l)imcthyl-/rani-2-pentene

3.3-Dimethyl-l-pentene

233-Tnmethyl-l-butene

3-Methyl-M-penta-diene

trans-l ,3,5-Hexatriene

as- 1 3,5-H exatnene3-Methyl-l.2-penta-

diene2,4-Hexadiene

3-Methyl-l,5-hexa-diene

4,4-Dimethyl-l,2-pentadiene (len-Butylallene)

1 3-C'yclohexadiene

4,4-Dimethyl-Oi-2-pentene

Boilingpoint,

•c

72

7 2 3 2 5

7249

73

7 3 2 175752758

76

76

76

763

7675

7754

7787

780 3

785,77 85

78579 70

79481 6765

80-1

80-3

80 3 1'57

8042

Meltingpoint,

•c

-1366

-7428

-127

-11524

-1343

-10985

-79

-1048

-13546

"B

1 425

1 4402"

1 3918

1 438

1 41221 4451 43061 4330

1 446

1 4282

1 446

1 451

1 3982

1 3984

1 4029

1 4494

1 4884 ""

1 45771425

1 4493

1 4116

1 4740

1 4024

Di»

0 7 1 1

07057'"

06827

0705

0708007170779607802

0719

07149

0719

0719

06889

06974

07050

07499

0 74229 ii

071790715

07152

07103

07184

08413

06996


i-Bromo-

tetra-2 forms

di

di

telra-

di-

di-

di-

hexa-

2,5-rfi-tetra-

di-

tetra-2forms

di-

BP. 'C

77-8'

1303

928-93"

95 3 6'°

98-9"

85"

92830"

MP/C

a) 63 4 b)fp <-50

173 4 121

38-9

78

182

68, iso-menzes— m 1081 , irans-2,as-3,trans-4.92,l,as-2, irans-3, trans-4, 156

"B

1 4970

1 5850

1 5080

1 5109

1 534 '"

1 5080

DJ°

1 5129

2 1873

.

1 5538

1 5615

1 622 '"

1 5538

Miscellaneous

Mercaptosuccmicacidadduct, 11905

Maleicanh adduct,95 6, Igr , S02

adduct, 43-3 5

Maleicanh adduct.145-6, heptane,Benzoqumoneadduct, 196 7, Igr


14

TABLE II . O R G A N I C D E R I V A T I V E S OF A L K E N E S , C Y C L O A L K E N E S ,DIENES AND POLYENES

a) Liquids 1) (Listed in order of increasing b.p. )* (Continued)

No

80

81

82

8384

8586

87

8889

90

91

92

93

94

95

9697

98

99

100

101

102

103

104

Name

3,4-Dimethyl-l-pentene

Cyclohexene

2,4-Dimethyl-2-pentene

3-Methyl-l-hexene23-Dimethyl-l-

pentene3-Ethyl-l-pentene

5-Methyl-l-hexene

5-Methvl-(rans-2-hexene

2-Methyl-3-hexene2,4-Dimethyl-2,3-

pentadiene (Tetra-methylallene)

4-Methyl-l-hexene

3,4-Dime(hyl-2-pentene

4-Methyl-c/5-2-hexene

4-Methyl-(ranj-2-hexene

3,3-Dimethylcyclo-pentene

2-Ethyl-3-methyl-l-butene

5-Methyl-ns-2-hexene5-Methyl-l,4-hexa-diene

2-Methyl-l-hexene


2-Methyl-l,5-hexa-diene

2,4-Dimethyl-l,3-pentadiene


3-Methyl-(ranj-3-hexene

1-Heptene

Boilingpoint

°C

81

8297

83-4

8408426

85 13

85 31

860

860865

8673

870

8737

876

88

89

9191-25

920

92

92 5™9

93

932

93 5

9364

Meltingpoint•c

-10351

-1277

-1348

-1274

-141 45

-1265

- 102 84

-114

-11903

"S

1 3995

1 44654

1 4016522

1 3971 4033

1 3980

1 3966

1 400

1 3991 40039

1 4000

1 407

1 4024

1 4023

1 423

1 410

1 4001 4390

1 4034

1 428

1423/6'73

1 4412

1 4283

1 4107

1 39980

DJ°

0701

081096

0 695822

069507051

06962

06920

0700

069407006

06985

0713

06996

06975

0771

0715

070007258

07030

0766

07289"5

07368

0779

07099

0 69698


x-Bromo-

dl-

dl-

dl-

di-

di-di-

di-

di-

di-

di-

di-

di-

di-

di-\,2-di-

di-

di-

BP "C

101 3'3

88"

84 0- 26

725-30"

9351S

142636""

87 81 U

96"

947-57"

655 60

91 2"

91 2"

72535 J

89 90"101 4"

10051 523

106 2'3

M P 'C "*D

1 5445"

1 5092022 s

1 50281 5028

1 5006

1 4970

1 4960

1 5060

1 4980

1 5104

1 5045

1 5045

1 5062

1 49901 5233"

1 5000

1 4990

D;°

1 7759"

1 54312!S

1 52481 5245

1 5251

1 5072

1 5027

1 5310

1 5027

1 5400

1 5382

1 5382

1 5261

1 51521 566"

1 5066

1 5208

Miscellaneous

Mercaptosuccmicacid adduct, 1 50 51 5,KMnO,oxid — • adipicac ,154, 2,4-Dimtro-phenylsulfenylchloride, 117 8HBr — cyclo-hexyl bromide,bp 165

Nitrosochlonde,75 6

Mercaptosuccmicacid adduct103 4- 9


15

TABLE n. O R G A N I C D E R I V A T I V E S OF A L K E N E S , CYCLOALKENES,DIENES AND POLYENES


No

105

106107

108109

110

1 1 1

112

113

114115116117

118

119120

121

122

123124

125126127

128

12913031

32

33

34

35

36

37383940

Name

3-MethyI-//-an?-2-hexene

2-Ethyl-t-pentene3-Methyl-c«-3-

hexenc2-Methyl-2-hexenetrans-3-Heptene

ra-3-Heptene

5-Me«hyl-l,2-hexa-diene(Isobutylallene)

3-Ethyl-2-pentene

2,3-Dimethyl-2-pentene

tranS'2-Heptene3-Ethylcyclopentenecu-2-Heptene5-Methyl-l ,3-cyclo-

hexadiene2,2-Dimethyl-rran.r-3-hexene

1,4-Heptadiene2,4,4-Tnmethyl-

1-pentene3,3-Dimethyl-l,5-

hexadiene3,4-Dimethyl-1,5-

hexadiene2,5-Dimethyl-3-hexene5,5-Dimelhyl-l-

hexene4-Methylcyclohexene3-Methylcyclohexene2-Isopropyl-3-

methyl-1-butene3,4,4-Tnmethyl-l-

pentene3,5-Dimethyl-l-hexene3,3-Dimethyl-l-hexene5,5-Dimetliy\-trans-2-hexene

2,4,4-Trimethyl-2-pentene

3,3,4-Tnmethyl-l-pentene

2,2-Dime«hyl-c«-3-hexene

1,2-Heptadiene (n-Butylallene)


4-Ethylcyclopentene4,4-Dimethyl-2-hexene1-Ethylcyclopentene5,5-Dimethyl-cw-2-hexene

Boilingpoint

•c

940

949535

95419567

95 75

96

9601

975

979598 19851005

1 5762

1009

101101 44

101 6

101 8

1021025

102741040104

104

104104104 1

10491

105

1054

105 5 60

1058

10610610631069

Meltingpoint

•c

-13035-13663

-1183

-10948

-9348

-1155

-10633

-1374

-904

-1184

nf?

1 410

1 4051 4123

1 41061 4043

1 4059

1 4282"

1 4148

1 4208

1 40451 43191 4061 4662 ""

\ 4063

1 42021 4086

1 4160

1 4211

1 4061 4049

1 44141 44441 4085

1 412

I 4041 40701 4055

1 4160

1 4144

1 4099

1 432"

1 4448

1 4401 4131 44101 4113

D;°

07120

070807132

0708206981

07030

07225'"

07204

07277

0701207830070808252

07039

0710607150

07249

07304

07100709

07947080100722

0719

07080714007066

07218

0729

07128

0 7306"1

07976

079807220798207169


x Bromo

di-

di-

di-di-

di-

di-

di-

di-

di-

di-

di-

di-

di-

2,1-dt-

letra-

di-

B P . ' C

6505 1'

77 84

7 3 0 l »105565 2 '

105 5-652 3

76 0- 4s

97 9"

96 2 "

96 2 "

965-708

109"

13040

108-IO'2 ,1403

92 34

M P. 'C "B

1 5040

1 4990

1 49901 5010

1 5010

1 5090

1 51722

1 5000

1 5000

1 5032

1 5734

1 5058

1 520018

1 5718

1 5113

D°»

1 5240

1 4929

1 51161 5153

1 5153

1 S426

1 54722

1 5129

1 5129

1 4856

2091

1 5034

1 6501?

1 5595"

20675

1 5148

Miscellaneous

)envative data given in order m p , crystal color, solvent from which crystallized

16

TABLE II . O R G A N I C D E R I V A T I V E S OF A L K E N E S , C Y C L O A L K E N E S ,DIENES A N D P O L Y E N E S


No

141

142

143

144145

146147

148

149

150

151

152

153

154

155

156

157158

159

160161162163164165166

167168

169170171172173

174

Name

2-Methyl-2,4-hexadiene

2-Methyl-13-cyclo-hexadiene

3-Melhvl-2,4-hexadiene

4,4-Dimethyl-l-hexene3-Ethyl-4-methyl-l-

pentene2,4-Heptadiene2,4-Dimelhyl-/ranv-3-

hexeneQuadricyclene (Quad-ncyclo[2,2,l,0">.O3 ' ] heptane)

23,4-Trimethyl-l-pentene

4-Methyl-13-hexadiene

23,3-Trimethyl-l-pentene

4,5-Dimcthyl-l-hexene

1,5,5-Trimethylcyclo-pentene (Iso-laurolene)

2,4-Dimethyl-cw-3-hexene

3,3-Dimethyl-2-ethyl-

1-butene3-Ethyl-2-methyl-l-pentene

4,5-I)ime(hyl-2-hexene1-Methylcyclohexene

2-EthyM-methyl-l-pentene

3-Ethyl-l-hexene2,3-Dirnethyl-l-hexene2,4-Dimethyl-2-hexene3-Methyl-l-heptene2,4-Dimethyl-l-hexene2,5-Dimethyl-l-hexene3-EthyI-3-methyl-l-pentene

3,4-Dimethyl-l-hexene3,4,4-Trimethyl-2-

pentene3,S-Dimethyl-2-hexene2-Methyl-3-heptene5-Methyl-3-heptene2,5-Dimethyl-2-hexene3-Methyl-l,5-heptadiene

2-Ethyl-3-methyl-l-pentene

Boilingpoint

•c

107

107 8

107 8

1072

1075

107 5 801076

108"° si d

108

108 10

1083

109

109'"

109

110

110

10100

103

103105106II

11 211 612

1212

121212122125

125

Meltingpoint

•c

-69

-121

nb°

1 426621

1 4662 '»

1 46I46IS

1 41021 4097

1 45781 4126

1 4804

1 415

1 4523

1 4174

1 414

1 4324

1 4140

1 4159

1 415

1 4131 4503

1 4105

1 4071 41131 41181 4061 41101 41051 418

1 4131 4232

1 4161 4021 410

4140423022 5

4142

D;»

07439

08272!!

07625"

0719807200

0738407145

0729

07558

07352

0728

07824

07178

0728

0730

072508102

07195

071507214072130711

07200717207305

072407395

072507060713

0720

0729


x-Bromo-

di-

d,-

di-

BP 'C

224 5

100 2"

8813

M P 'C "5

1 5003

1 4740

D;°

1 4689

3980

Miscellaneous

Reduces Tollen'sreagent on warm-ing

2,4-Dimtrophenyl-sulfenyl chloride.139 40

* Derivative data given in order m p , crystal color, solvent from which crystallized

17

TABLE II . O R G A N I C D E R I V A T I V E S OF A L K E N E S , C Y C L O A L K E N E S ,DIENES AND POLYENES


No

175176177178179180181182183184

185

186

187

188

189

191

192193194

195

196

197

198199200201

202203

204

205

206207208209

Name

4-Methyl-l-heplene6- \lelhyl-3-heptene4-Ethyl-l-hexene4-Ethyl-2-hexene2-Isopropyi-l-pentene5-Methyl-l-heptene4-Methyl-2-heptene2,3-Dimethyl-3-hexene4-Methyl-2-octene2.4-Dimethyl-2,4-

hexadiene6-Methyl-2,4-

heptadiene3-Ethyl-4-methyl-

trans-2-penteneCycloheptene(Suberene)

1 -Methyl- 1,4-cyclo-hexadiene

3-Ethyl-4-methyl-cw-2-pentene

1,3,5-Cycloheptatriene(Tropihdene)

3,4-Dimethyl-2-hexene3-Ethyl-3-hexene6-Methyl-l,3-

heptadiene2,5-Dimethyl-I,3-

hexadiene2,3,4-Trimethyl-2-

pentene4,4-Dimethvlcyclo-

hexene6-Melhyl-2-heptene2-n-Propyl-l-pentene5-Methyl-2-heptene3,3-Dimethylcyclo-

hexene2-Methyl-l-heplene2,5-Dimethyl-l,5-

hexadiene

2-Ethyl-l-hexene

rf/-l,2,3-Trimethyl-cyclopentene(Laurolene)

4-Methyl-3-heptene3-Ethyl-2-hexene3-Methyl-3-heptene1-Octene

Boilingpoint

•c

1 1 2 8113"'1131131131 1 3 31135 4 1114114114-5

114 6

1143

11438

1145-48

115

115 5

116116116 8

116 8

1163

11698

1171 1 7 7118119

119 22119 23

120

120 I7"

1204121121121 28

Meltingpoint

•c

-56

<-70

-7949

>-80

-1133

-805

-8738solid at-80, hqat -23

-101 76

"D

410411441241241440944096416410025

4545716 -,

1 4397"

1 4210

1 4580

T4703

1 424

1 5243

1 4181 418

1 45024

1 4275

1 4420

1 4121 41361 4141 445

1 411951 45054

1 4157

1 4421

1 4171225

1 4241 4181 40870

Df

0 7 1 7072560726072507250716407154072807188"07635'65

0704 125

07350

08254

0848

0739

07370729074(22

07412

07434

07996

07180724007230804

0 7202507637

07270

07950

0741 125

07370728071492


x-Bromo-

di-

di-

tetra-

di-

BP. 'C

unstable

240 2,11851 5

M P 'C

97

171

ng

1 4970

D?

1 4580

Miscellaneous

Nitrosochlonde,118 Oxid —pimelicac , 105

Maleic anh adduct.1042-50,00,

Mercaptosuccimcacid adduct.101 9-27

Mercaptosuccimcacid adduct,96 1-6


18

TABLE II . O R G A N I C

a) Liquids

D E R I V A T I V E S OF A L K E N E S , CYCLOALKENES,DIENES AND POLYENES

1) (Listed in order of increasing b.p.)* (Continued)

No

210

211

212213

214215

216

217218

219220

221222

223

224

225

226

227

228

229

230231232

233

234235

236237

238239

240

241

Name

trans-4-Octene

1 ,3-Cycloheptadiene(Hydrotropilidene)

3-Methyl-2-heptenem-4-Octene

2,3-Dimethyl-2-hexene3,4-Dimethy\-trans-3-

hexene6-Methyl-l-heptene

c«-3-Octenefrans-3-Octene

2-Methyl-2-heptene(rans-2-Octene

m-2-Octene2-Methyl-l,3-hepta-

diene1 ,4-Dmiethy Icyclo-hexene

1 ,5-Dimethylcyclo-hexene

2,6-Dimethyl 2-heptene

4-Vmylcyclohexene

4-Methyl-2,4-hepta-diene

3,4-Dimethyl-2,4-hexadiene

3-Methyl-2,4-hepta-diene

Bicyclo[4,2,0]oct-7-ene4-Ethylcyclohexene1 ,6-Dimethylcyclo-hexene

3.5-Dimethy 1-2,4-heptadiene

2,4-Octadiene2,5-Dimethyl-2,4-

hexadiene3-Ethylcyclohexene1,2,3,3-Tetramethyl-cyclopentene(Campholene)

1-Ethylcyclohexene1 ,2-Dimethylcyclo-hexene

1,3-Dimethylcyclo-hexene

Bicyclo[4,2,OJoct-2-ene

Boilingpoint•c

121 4"9

121 52

121 612i 7^9

121 8122

122 4113 5

122 374'1224'"

123 51250

12564127 8 '

128

128

1289

1295305 36"

131 2

132 471 3

132 5

1325133133

133 44 •

1335 401336 28'

134134 5

3637

137

37 9

Meltingpoint

•c

fp -94

-11042

fp -118

-115 1

f p -126

f p-1104

-877

-1002

146 8

"D

1 41157

1 41831 41361

1 42681 430

1 4070

1 412461 41241

1 41381 4132

1 41501 4432

1 446

1 448

1 412

1 4623

1 4621

1 4410

1 4649

1 47611 4491 454

1 4487

1 4542'1 4796 I J

1 4511 44406

1 45751 4588

1 445

1 4810JU

Dj°

071467

0 8929?

072960 72048

074080747

07125

071888071630

0724107199

0724307432

0802

08051

0722

08320

07551

07832

07667

08100815

07728

07427'0 7646 "

081408035

082308250

0802

08948


x Bromo

di(meso)

di (dl)

di

aftdi

di

tetra

di

BP C

103»

84084"

85 7'

74"

M F C

695 70eth

101

142 3acet

"i>

1 4967"

1 4981

1 5060

D{°

1 4525

1 4569

1 387

Miscellaneous

H, — Cycloheptane b p118 20

Mercaptosuccmicacid adduct1429 35

Nitrosochlonde83 4

Nitrosochlonde118 9

H B r ^ D i h y d r obromide b p109 1 1 "

Oxid in air — »-polymenc peroxide 59

Nitrosochlonde58 60

'Derivative data given in order m p crystal color solvent from which crystallized

19

TABLE II . O R G A N I C D E R I V A T I V E S OF ALKENES, CYCLOALKENES,DIENES AND POLYENES


No

243

244245

246

247

248

249

250

251

252

253254

255

256

257258

259

260

261

Name

1-Mcthylcycloheptene

2-Methyl-4-octenea-Fenchene(l,55-Tn-methylbicyclo[2,2,l]hept-2-ene)

1,5,5-Tnmethylcyclo-hexene (o-Cyclo-geraniolene)

2,6-l)lmethyl-2,4-heptadiene

1 ,4,4-Tnmethylcyclo-hexene (Pulenene)

1 ,5,6-Tnmethylcyclo-hexene

23-Dimethyl-2-nor-bornene (Santene2,3-Dimethylbicyclo[2,2,l]-hept-2-ene)

2,6-Dimethyl-U-heptadiene (Iso-geraniolene)

Cyclooctatetraene

7-Methyl-3-octene2,6-Dimethyl-l,5-

heptadiene(Geraniolene)

1,8-Nonadiene '

1,3.5-Trimethylcyclo-hexene (Tetrahydro-mesitylene)

3-Methyl-2-octeneCydooctene

3,6-Dimethyl-2,4-heptadiene

4-Nonene

1,4,5-Trimethylcyclo-hexene

Boilingpoint,

°C

1375 85

138"J

139 40

139-41 "

139 437 '

1395-405

140

140-1,35'

140-2.31

14056142 3,42 2 5 '

14! 74.

141-2,165 70

141-4

142 5-3 5

143-5734

1438-45773

144-6

144-6,44 6'2

144-6

Meltingpoint

•c

-468,-7

-70

"5

1 4581

1 41811 44862

1 44612"

1 4587"

1 444" '

1 4572

1 46699

1 4606"

1 5290

1 41681 44361"

1 4302

1 449135

1 42471 4693

1 46335 14

1 42I218

1 4482

Df

08243"

0739208433

07981"

0 74820

08032""-

083U,

08640

07923"

09206

072780 7626"

07511

08025'4i

0 740925

0 7853°

0732'8

0805


x Bromo

di-

di-

BP 'C

12005'"

11920"

M P °C <

1 5247"

1 4988"

D;°

1 5324"

1 410"

Miscellaneous

Nitrosochlonde,106, Nitrosate,97 8

Nitrosochlonde,131

Nitrosochlonde,100 20, aq me , alNitrosate, 102 4

Nitrosochlonde,118 22. et ac

Dichlonde 88 9,Nitrosdte, 216d ,Nitrosochlonde,109 10 Nitrosite,3 forms a) 122 4,bl b ) !27-8 ,g rn ,c) 104, col

Mdleicdnh adduct,167 8 Benzo-qumoneddduct.141, dl Acrylic acddduct 112 3, IgrAgNOiddduct,173 4

Nitrosochlonde,134

Br2 — » Bromocyclo-octene, b p 7-823,n2

D° 1 5182, Di-chlonde, b p1304-06",mp-5, rig" 1 5061,D2° 1 1620


20

TABLE II. ORGANIC DERIVATIVES OF ALKENES, CYCLOALKENES,DIENES AND POLYENES


No

262

263264

265

266

267

268269270

271

272

273

274

275276

277

278

279

280281

282

283

284

285

286

Name

1-Vinylcyclohexene

as- 1 ,4-Cy clooctadiene1 ,3,5-Cyclooctatriene

4,4-Dimethyl-l,7-octadiene

£-Fenchene (2,7,7-Tn-methylbicyclo[2,2,l]hept-2-ene)

1,6,6-Trimethylcyclo-hexene

1-Nonene3-Nonene1 ,5-Cyclooctadiene

4-Methyl-3,5-octa-diene

7-Methyl-2,4-octa-diene

l-Ethyl-4-methyl-cyclohexene


2-Nonene1,23-Trimethylcyclo-hexene


/S-Fenchene (2,2 Di-methyl-5-methylene-bicyclo[2,2,l]heptane)

2,6-Dimethyl-2,5-heptadiene

2,7-NonadieneAllylcyclohexane (3-Cyclohexylpropene)

l-Ethylidene-4-melhyl-cyclohexane

4,5-Dimethyl-2,6-octadiene

l-Ethylidene-3-methylcyclohexane



Boilingpoint,

•c

145,63 553

145 |"8

145 6,76"°

145 8

146268»2

1462-7 2767,144 6

14687147 475"148 9

148 51

149

149, 153 4

149 51

1494 991496

ISO749

150

1505 3 5

1506 10

1506151

152-3

1529-38

153

153-5

55 67M

Meltingpoint,

°C

-53

-81 37

-725

"D

1 4950"

1 5035"

1 4330

1 4865

1 45620 '

1 415721 41731 4905

1 46285 !5

1 4543 '»

1 453"

1 454

1 4202'1 463"

1 452725

1 46511

1 4490

1 43581 4536"

1 457 12 '

1 43752S

14584

1 44453

1 4385"

Df

08754089712S

07647

08626

082172 0 3

072940881824

0 7640"

07521"

08169"

08296

07382 '08347'2

0812"

08599

074990819613

0812 '

0761 125

0813511

07767

07605"


x-Bromo-

tetra-

di-

lelra-

di-

di-

B P . ' C

141 520

184"

143 4"

M P/C

139

81-2

<

1 4942

D;°

1 3980

1 537°

Miscellaneous

50°/0H2S04 —

dimer .bp 118-95

Maleicanh adduct.144-5, AgNO3

adduct, 125-6, al

MS -24 1

Nitrosochlonde,133 4,et ac

N-Bromosuccmi-mide — * bromo-cyclooctadiene,b p 64", ng1 5410, Df 1 3420

Nitrosochlonde,2 forms a) 103-4,pr , eth , b) 98 9,cr , eth

[<*]g +625,Nitrosochlonde,120

Nitrosochlonde,2 forms a) 117-8,least soluble, b)1 1 3-4, more soluble

Nitrosochlonde,114, acet


21

TABLE II. ORGANIC DERIVATIVES OF ALKENES, CYCLOALKENES,DIENES AND POLYENES


No

287

288

289

290

29!

292

293

294

295

296

297

298

299

300

301

302

303

304

305

306

Name

a-Pinene

l-Ethylidenc-2-methylcyclohexane

2,4-Dimcthyl-2,4-octadiene

1,4,4-Trimethylcyclo-heptene (Eucarvene)

iS-Pinene (Nopmene,Pseudopmene)



/-4-Carene (3,7,7-Tn-methylbicyclo[2,2, 1 ]hept-2-ene)

Myrcene (2-Methyl-6-methylene-2,7-octadiene)


/-3-Carene (3,7,7-Tn-methylbicyclo[2,2,lj-hepi-3-ene)

3,8-o-Menthadiene(m-3-Isopropenyl-4-methylcyclo-hexene)

5-Decene

/>-8-Men«hene(l-Isopropenyl-4-methyl-cyclohexane)

(/-m-8-iV1enthene(l-Isopropenyl-3-methylcyclohexane)

/-m-8-Menthene(l-Isopropenyl-3-methylcyclohexane)

6,8-o-Menthadiene (3-Isopropenyl-2-methylcyclohexene)

5,8-o-Menthadicne (4-Isopropenyl-3-methylcyclohexene)

1-Decene

4-Decene

Boilingpoint,

°C

1560-63

158

161 3746

161-5720

163-4

1635 45

164-7,58"

16557 Q707

166

168, 56"

168 9705,123 4200

169-70

170"°

170

170

70-1

170 1

170-1

7057

1706

Meltingpoint,•c

-50

-112 to-111

-6631

"S

1 4560

1 47

1 4558" •

1 4561

1 4782

1 44814

1 456

1 47430

1 4722

1 45245 ">

1 46930

1 4749

1 4260

1 4523

1 4546

1 4574

1 4758

1 4778

1 42146

1 4243

Df

08600

0823°

0 78028 •

08185

08694

07849

07933

0 8552i»

07982

07752 '

0 8586i°

08507

07474

08142

08179

08189

08481

084901?

074081

07404


x Bromo

di-

tetra-

di-

di-

BP. 'C

119'

145160"

M P . ' C

169 70, al

124-7

"S

1 4912

1 489 124

D?

1 3484

1 32428

Miscellaneous

Nitrosochlonde,109, Hydro-bromide, 89,Nitrosobromide,91 2d,AcidKMnO4 — pinonicac , 103-5

WD -22

k]3D° +62 2

Maleicanh adduct,33-4, 1,4-Naph-thoqumoneadduct, 81

Methiodide, 130d

WD" +769,Nitrosochlonde,100-1

No +973

WD -»06

Mercaptosuccmicacid adduct,935-8


22

TABLE II . O R G A N I C

a) Liquids

D E R I V A T I V E S OF A L K E N E S , CYCLOALKENES,DIENES AND POLYENES

1) (Listed in order of increasing b.p.)* (Continued)

No

307

308

309

310

311

312

313

314

315

316

317

318

319

320

321

322

323

Name

p-Menthene(l-Iso-propylidene-4-methylcyclohexane)

I-Isopropenyl-1,4-cyclohexadiene

o-Menthene(l-Iso-propylidene-2-methylcyclohexane)

m-Menthene ( 1 -Iso-propylidene-3-rnethylcyclohexane)

a-Terpinene ( 1 -Iso-propyl-4-methyl-1 ,3-cyclohexadiene)

2,4-p-Menthadiene(2-Isopropyl-5-methyl-1 ,3-cyclohexadiene)

/-5-lsopropyl-2-methyl-U-cyclo-hexadiene

1,5-p-Menthadiene(5-Isopropyl-2-methyl-l,3-cyclo-hexadiene)

rf-Silvestrene

rf-Limonenc

Isocarvestrene (5-Iso-propenyl-1-methyl-cyclohexene)

/-3~Isoproppnv|-l-methylcyclohexene

Dipentene (d 1-Limonene)

3,8-m-Menthadiene(l-Isopropenyl-5-methylcyclohexene)

Menogerene (5-Iso-propyhdene-2-methyl-l,3-cyclo-hexadiene)

-y-Terpinene (1-Iso-propyl-4-methyl- 1 ,4-cyclohexadiene)

d /-2,8-m-M enthadiene(l-IsopropenyI-3-methylcyclohexene)

Boilingpoint•c

172-4

172-6

173, 160-2

173-5

173 548755

174 6

174-7

175 6

175 8

176 64

176 7765

176-8

1776-80

,79730

180 I789

183

184 7

Meltingpoint,

•c "5

1 4568

1 5216

1 467

1 4670

1 477

1 484527

1 4732

1 4777

1 4760

1 4743

1 4804

1 476 118

1 472720

1 4972

1 5005

1 476514 5

1 503

Df

081921

09068

08345

08214

08375

08441g

08425

0 84632S

08479

08411

08496

0 848"

0 840220

08672

0849

086418


x-Bromo-

letra-

tetra-

letra-

letra-

tetra-

di-

tetra-

B P . ' C M P, 'C

113

135

104

137-8, meal -chl

125,eth

115

129-30,pet eth

"S DfMiscellaneous

Nitrosochloride,101-3

Dihydrochlonde,53-4, me al , Di-hydrobromide,58 9, me al , Di-hydroiodide, 76,me ai , Nitrosite,155, Maleicanhadduct, 62, 66-7

[a]ff -11276,Nitrosite, a 120-1,0 105 6

[a]D +49 1, Nitro-site, a 11 3-4, ,8105 Maleicanhadduct, 126-7, peteth

Dihydrochlonde,72, Nitrosochlo-ride, 106-7

Nitrosochloride,100-4, 2,4-Dimtro-phenylsulfenylchloride, 195-6

Dihydrochlonde,71 5, me al

[a]i> -68 2, Di-hydrochlonde, 72

Dihydrochlonde,50-l,al

[a]D +175

[«)b5 +36, Nitro-sochloride, 111,Nitrosate, 116d ,ac a -me al


23

TABLE II. ORGANIC DERIVATIVES OF ALKENES, CYCLOALKENES,DIENES A N D POLYENES


No

324

325

326

327

328

329

330

331

332

333

334

335

336337

338

Name

Menogene (3-Iso-propyhdene-6-methylcyclohexene

Terpinolene (4-Iso-propylidene-lmethylcyclohexene)

2-Undecene(2-Hendecene)

5-Undecene (5-Hendecene)

1-Undecene(1-Undecene)

m-Cyclodecene

1-Dodecene

1-Tridecene

1-Tetradecene

Cedrene

1-Pentadecene

1-Hexadecene

1-Heptadecene2-MeIhyl-2-hepta-decene

1-Octadecene

Boilingpoint,

•c

18467645

186

192 3,78 5'4

1922

19267

194 574"

2133688 7'°

23278104 510

251 1,1190'°

262-3,124 612

268 17.133 710

28441039'

2997, 116'314, 277'°°

3142,128'

Meltingpoint,

•c

-49 19

-3523

-2307

-1285

-373

4 12

11 2-25

176

"D

1 5026

1 4883

1 43325

1 4289

1 42609

1 4854

1 43002

1 4336

1 43631

1 5001"

1 4389

1 44120

1 4432

1 4449

Df

08624

0 8633,'?

077351?

07511

0 75032

08770

0 75836

07653

07713

09359!?

077641

078112

0785207953

07888


r-Bromo

dl-telra-2forms

di-

di-

dt-

di-

di-

di-

di-

di-

di-

B P 'C

145 6»

186"

204-5'7

225 7'5

267-828

M P "C

69 70a) 119,ac a ,b)122

121

-15

0

135,a i

24, al

ng

1 4916

1 4897

D;°

1 3122

I 2235

Miscellaneous

Nitrosite, 155, meal orchl , Maletcanh adduct, 205 8

Maleicanh adduct.182

O3 — » Sebacic acid.1345

Mercaptosuccmtcacid adduct,1040 8

!%HotKMnO 4 —n pentadecylic ac ,52 3, Mercapto-succimc acid ad-duct, 105 0 8


24

TABLE II . O R G A N I C D E R I V A T I V E S OF ALKENES, C Y C L O A L K E N E S ,DIENES AND POLYENES

a) Liquids 2) (B.p. at reduced pressure only. Listed alphabetically)

No

123456789

1011

1213

14151617

Name

Bicyclo[12,2,2joctadeca-14,16,18-trieneBicycle [4,2,0)oct-3-eneButylcyclooctatetraeneIranj-Cyclodecene1,5,9,13-CyclohexadecatetraeneIran.t-Cyclononene1 3-Cyclooctadecadiene1 ,3-Cyclooctadiene1 ,3,6-Cyclooctalriene1 ,3-Cvclotetradecadiene1 ,2-Dimethylcyclooctalef raene

2,6-Dimethyl-2,5-octadieneEthylcyclooctatetraene

5-MethylcyclohepteneMethylcyclooctatetraene7-PentadecenePropylcyclooctatetraene

Boilingpoint, "C

1635 4 5 5 5

81"°9g20

68-70'"93 8°"

73 430

1153

482S

6860

106-83

10796

590-5"813'

69 7038

84 5<"

11432

73"

Meltingpoint, 'C

-57 to -55-62to-56

"£

1 5204"1 48321 50832S

1 48221 54721 47991 48991 494025

1 49821 5219"

1 45001 518725

1 4201631

1 524926

1 44201 513125

D;°

0 887625

08672

08615088140 869925

0 894025

0 872325

0 895025

07330 8996M

0760613'0 8978 25

077650 88702S

Miscellaneous

Maleicanh adduct, 143 4

O, — Sebacic acid, 1 34 5

Phenylazide adduct, 97 8 8 2

Nitrosochlonde, 109-10, Nitrosate, 21 OdMaleic anh adduct, 184 5-5 5, bz -Igr , AgNO3

adduct, 1425 4 5, al

Maleic anh adduct, 97 8 5, bz -cyclohexane.AgNO3 adduct, 124-5 5, al

*Derivative data given in order m p , crystal color, solvent from which crystallized

25

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TABLE II. ORGANIC DERIVATIVES OF ALKENES, CYCLOALKENES ...chemistry.gsu.edu/files/2014/11/Alkenes.pdf · table ii. organic derivatives of alkenes, cycloalkenes, dienes and polyenes