TABLE III. O R G A N I C D E R I V A T I V E S OF A L K Y N E S (ACETYLENES)
a) Liquids (Listed in order of increasing b.p.)*
Hydration product (RC^CR' — RCOCH,R )
and its derivatives
No
1
Name
Ethyne (Acetylene)
2 Propyne (Methyl
acetylene)
3 1-Butyne (Ethyl
acetylene)
4 1,3-Butadiyne
(Diacetylene)
5 3-Methyl-l-butyne
(Isopropyl acetylene)
6 2-Butyne (Dimethyl
acetylene)
7 3-Methyl-3-buten-l-yne
(Isopropenyl acetylene)
8 3,3-Dimethyl-l-butyne
(tert-Butyl acetylene)
9 1-Pentyne(Propyl
acetylene)
10 l-Penten-4-yne(Allyl
acetylene)
Boiling
point, "C
Melting
point, *C
Bp.'C
2,4-DinitroSemicarphenyl- bazone of
hydrazone ketone
of ketone
Hg salt
-808,
subl
06179-" 4 (Acetaldehyde)
(202)
(168)
(162-3)
-1027
06I74- 2 1 Acetone
56
128
190
204
8 09, 8 3
-12572
1 3962
0 6682"
82
116-7
135 6
162 3,al
103
-35 to
-36
1 4120
07249
2635,28
-897
1 3723
0666
272 6
-3226
1 3921
06901
38 9
-81 20
1 37725
40 18
-105 7
1 3852
42-3
720 5
73 5
75 0- 5.
55-6
78-83
81 5'44
2-Butanone
82
15
135 6
112, 106 1184
06737' 5
06901
2 Pentanone 1023
145
1 4125" 0738"
Allyl methyl 111 2
ketone
160
-1093
1 4377
07270
1 4039
07107
1 4496
0740]
155-7
2-Pentanone 1023
+
3-Pentanone 102
145
112, 106
156
138-9
1000- 5
1 3916
07037
74-5
-131 9
1 3989
07155
-11037
1 4078 ">
0716"
-45 to
-35
-51
2-Hexanone
128
106 7
125
1 4028
07154
1 443 12' 0 737521
1 41 1225
Tetrabromo denv ,
b p 275
1,2-Dibromoderiv ,
b p 795 80 510,
4,4,5,5-Tetrabromo
denv , b p 132 610
48
1 3936i5 0 709215
-105 1
Miscellaneous
161 5 20 KOBr— 1,4-Dibromo denv ,
49 50, bz
Tetrabromo denv ,
b p 275
Tetrabromo denv ,
243, eth , 2,4-Dinitrophenylsulfenyl chloride.
65 6
3,4-Dibromo denv ,
b p 500-1 5'°
92 5-3 0 Cusalt, 140, red
116 7
1 4330
59 2 60 1
61 1 2,
99
65 70"°,
577
71 33
2-Butanone
06801"
1 4158
33
13 2-Pentyne (Ethyl methyl 5607
acetylene)
21 1,4-Hexadiyne
22 3-Hexyne(Diethyl
acetylene)
Ketone
-840
(sat
press )
-2322
11 cw-3-Penten-l-yne
446
(cw-Propenyl acetylene)
12 (rani-3-penten-l-yne
522
(trans Propenyl
acetylene)
14 l-Penten-3-yne (Methyl
vinyl acetylene)
15 4-Methyl-l-pentyne
(Isobutyl acetylene)
16 3-Methyl-l-pentyne
(sec-Butyl acetylene)
17 1-Hexyne (Butyl
acetylene)
18 4-Methyl-2-pentyne
(Isopropyl methyl
acetylene)
19 4,4-Dinielhyl-l-pentyne
20 1,3-Pentadivne
D;°
"D°
0825?
0 7263"
1,2-Dibromoderiv ,
b p , 60-2'°, 3,4Dibromo denv ,
66-76'°
KMnO 4 —* formic
ac + propiomc ac
962 4
125 6 5
3-Hexanone
* Derivative data given in order m p , crystal color, solvent from which crystallized
28
125
130
112
2,4-Dimtrophenylsulfenyl chloride,
65 6
TABLE III. O R G A N I C DERIVATIVES OF A L K Y N E S (ACETYLENES)
a) Liquids (Listed in order of increasing b.p.)* (Continued)
Hydration product (RC=CR — RCOCH,R )
and its derivatives
No
Name
Boilmg
point °C
Melting
point °C
n
n
Ketone
23 4,4-Diniethyl-2-pentyne
(ten Butyl methyl
acetylene)
24 2-Hexyne( Methyl
propyl acetylene)
829 30
837 40
25 l-Hexen-3-yne (Ethyl
vinyl acetylene)
85""
26 l,S-Hexadien-3-yne
(Divmyl acetylene)
27 l-Hexen-4-yne
850
28 3-Ethyl-l-pentyne
29 1,5-Hexadiyne (Dipro
pargyl)
30 2-Hexen-4-yne
870 8 5
875
8 5 !"
20"
88 9
31 2-Methyl-3-hexyne
32 4-Methyl-2-hexyne
95 2
9594
46 4-Nonyne(n Butyl
propyl acetylene)
-8783
87 "
965
33 3-Ethyl-3-penten-l-yne
34 5-Methyl-3-heptyne
98 100 "
9974
35 l-Heptyne(n Pentyl
acetylene)
36 5-Methyl-2-hexyne
10246
37 8-Methyl-4-nonyne
1045
38 3-Heptyne (Ethyl propyl 105 6
acetylene)
39 2-Heptyne(n Butyl
1115 25
methyl acetylene)
40 2,2,5,5-Tetramethyl3-hexyne (Di tert-bMy\
acetylene)
41 1,6-Heptadiyne
42 l-Oc(yne(n Hexyl
acetylene)
43 4-Octyne (Dipropyl
acetylene)
44 3-Octyne (Butyl ethyl
acetylene)
45 2-Octyne (Hexyl methyl
acetylene)
-92
-4266
1 4071
07176
1 4135
07317
1 4522
07492
1 5045
07857
1 446"
0767"
1 4102
1 4381 21
07246
0 79943
1 4918
07710
-1167
1 4114
07263
073855
1 4170
fp
-10763
1 43382' 0 7886"
1 4102
07360
1 4087
B7328
-809
-9291
1 41762
1 4311
1 415
0 73776
07681
07337
1 4230
0748
1 1 1 9""
194
1 4055
07120
112 30i6
1262
-85
-793
1 451'
1 4159
08164"
07461
1304 67"
1 4226
07484
131 0-5
1 4261
0748
1380 4
14285
0761
150 4"2
1 42962S
Bp °C
24Di
Semicar
mtro
phenyl
bazone of
hydrazone ketone
of ketone
128
106 7
125
125
130
112
D;
0 7572S
2 Hexanone
+
3 Hexanonc
Hg salt
Miscellaneous
1 2 Dibromodenv
b p 8 7 0 5"
3 3 4 4 Tetr i
bromodenv b p
140 50 ">
1 2 Dibromodenv
b p 930 5'
1 2 4 5 Tetra
bromodenv b p
1 54 5 5 0"'
Allylethvl
ketone
745
65»"
95 106
2 Heptanone 151 2
89
123 127 61 me
al
4 Heptanone 144
75
132
2 Heptanone 151 2
+
3 Heptanone 148
89
123 127
101
2 Octanone
173
64 5 58
124 5
2-Octanone
+
3-Octanone
173
64 5 58
124 5
169
70""
187 8
64 5
1170 5
57 8
73 4
4-Nonanone
+
5-Nonanone
'Derivative data given in order m p , crystal color solvent from which crystallized
29
1884
90
804 7
me al
TABLE I I I . O R G A N I C D E R I V A T I V E S OF A L K Y N E S ( A C E T Y L E N E S )
a) Liquids (Listed in order of increasing b.p.)* (Continued)
Hydralion product (RCssCR1 — RCOCH,R')
and its derivatives
No
Name
Boiling
point, 'C
Melting
point, 'C
"D
D;°
Ketone
1 4217
07568
2-Nonanone 1953
55-6
118 20
1 4299
07616
3-Nonanone 187'51
+
4-Nonanone 187-8
55 6
111-2
57-8
73 4
157580 740
161
1 4850
0868
I 4331
0769
3-Nonanone 1877S1
+
2-Nonanone 1953
55-6
III 2
55 6
118 20
162,550- -2728
5'3
1740
-44
1 4490
08158
1 4265
07655
2-Decanone
2155
124
63,81
175-6
1 43321
0 7765Z1
3-Decanone
+
4-Decanone
5-Decanone
211
Cyclononanone
m p 34 146
2-Undecanone
Cyclodecanone
228
1508
47 1-Nonyne (Heptyl
acetylene
7
48 3-Nonyne (Methyl pentyl 153 5 «,
92"
acetylene)
49 Cyclooctyne
50 2-Nonyne (Methyl hexyl
acetylene)
51 1,8-Nonadiyne
52 1-Decyne (n-Octyl
acetylene)
53 3-Decyne (Ethyl hexyl
acetylene)
-50
Hgsalt
Miscellaneous
67 8-8 5,
me al
54 5-Decyne(Dibutyl
acetylene)
55 Cyclononyne
177, 10080
-73
1 4332
07688
177 8 740
-364
1 4890
08972
56 2,7-Nonadiyne
57 1-Undecyne ( 1 -Hendecyne, Nonyl acetylene)
58 Cyclodecyne
180
430
195,
-25
96 4330
203 4740
78 5 12
209'«,908
1 4674
1 4306
08332
07728
1 4950
08975
1 43802S
07816 M
215
89 09'°
234,
102 95'°
252,
1183I10
268
,297910
19
1 4340
07788
-5
14371
07842
0
1 4396
07888
10
1 4419
07928
284 103 3 15
1 4440
07965
59 6-Dodecyne (Dipentyl
acetylene)
60 1-Dodecyne (Decyl
acetylene)
61 1-Tridecyne (n-Undecyl
acetylene)
62 1-Tetradecyne (Dodecyl
acetylene)
63 1-Pentadecyne (Tridecyl
acetylene)
64 1-Hexadecvne (Tetradecyl acetylene)
2,4-DiSemicarnitrophenyl)azone of
Bp.'C
hydrazone ketone
of ketone
1
100 1
206 7
60 1 5
100 2"
800-7
63
51 2
57 5-8%0
NaNH 2 at210° —
1-Decyne, b p 174
184 5
122 0- 5 79
Ozonolysis —»
sebacic acid, 1 34 5
NaNH 2 -> 1Dodecyne, b p 215
203-5
842 8
'Derivative data given in order m p , crystal color, solvent from which crystallized
30