從石油 分離
從石油 精煉或聚合烴得到的混合物中分離
在催化劑 如:三氯化磷 存在下，在400℃和200巴下使正丁烷 與乙烯 的反應可以製造3-甲基戊烷 [ 15]
C
H
3
C
H
2
C
H
2
C
H
3
+
C
2
H
4
→
400
o
C
,
200
b
a
r
P
C
l
3
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
{\displaystyle \mathrm {CH_{3}CH_{2}CH_{2}CH_{3}+C_{2}H_{4}{\xrightarrow[{400^{o}C,200bar}]{PCl_{3}}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}} }
結構上，3-甲基戊烷由二部分組成：丁烷 （）和乙烷 （
CH
3
CH
2
{\displaystyle {\ce {CH3CH2}}}
因此，製備純3-甲基戊烷的最簡單的方法是：[ 16]
1.仲丁基 鹵化物 與 乙基鋰 或 丁基鋰 與 乙基鹵化物 反應
C
H
3
C
H
2
C
H
2
X
C
H
3
+
2
L
i
→
|
E
t
2
O
|
C
H
3
C
H
2
C
H
2
L
i
C
H
3
+
L
i
X
{\displaystyle \mathrm {CH_{3}CH_{2}CH_{2}XCH_{3}+2Li{\xrightarrow {|Et_{2}O|}}CH_{3}CH_{2}CH_{2}LiCH_{3}+LiX} }
C
H
3
C
H
2
X
+
C
H
3
C
H
2
C
H
2
X
C
H
3
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
L
i
X
{\displaystyle \mathrm {CH_{3}CH_{2}X+CH_{3}CH_{2}CH_{2}XCH_{3}{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+LiX} }
或
C
H
3
C
H
2
X
+
2
L
i
→
|
E
t
2
O
|
C
H
3
C
H
2
L
i
+
L
i
X
{\displaystyle \mathrm {CH_{3}CH_{2}X+2Li{\xrightarrow {|Et_{2}O|}}CH_{3}CH_{2}Li+LiX} }
C
H
3
C
H
2
L
i
+
C
H
3
C
H
2
C
H
2
X
C
H
3
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
L
i
X
{\displaystyle \mathrm {CH_{3}CH_{2}Li+CH_{3}CH_{2}CH_{2}XCH_{3}{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+LiX} }
2.武慈(Wurtz)反應 可以得到該產品的混合物：[ 17]
C
H
3
C
H
2
X
+
C
H
3
C
H
2
C
H
2
X
C
H
3
+
6
N
a
→
C
H
3
C
H
2
C
H
2
C
H
3
+
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
C
H
(
C
H
3
)
C
H
2
C
H
3
+
6
N
a
X
{\displaystyle \mathrm {CH_{3}CH_{2}X+CH_{3}CH_{2}CH_{2}XCH_{3}+6Na{\xrightarrow {}}CH_{3}CH_{2}CH_{2}CH_{3}+CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+CH_{3}CH_{2}CH(CH_{3})CHCH(CH_{3})CH_{2}CH_{3}+6NaX} }
產生氫 ，即金屬 +酸 (H+ )：[ 18]
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
2
X
+
Z
n
+
H
X
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
Z
n
X
2
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}X+Zn+HX{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+ZnX_{2}} }
或
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
X
C
H
3
+
Z
n
+
H
X
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
Z
n
X
2
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CHXCH_{3}+Zn+HX{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+ZnX_{2}} }
或
C
H
3
C
H
2
C
X
(
C
H
3
)
C
H
2
C
H
3
+
Z
n
+
H
X
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
Z
n
X
2
{\displaystyle \mathrm {CH_{3}CH_{2}CX(CH_{3})CH_{2}CH_{3}+Zn+HX{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+ZnX_{2}} }
或
(
C
H
3
C
H
2
)
2
C
H
C
H
2
X
+
Z
n
+
H
X
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
Z
n
X
2
{\displaystyle \mathrm {(CH_{3}CH_{2})_{2}CHCH_{2}X+Zn+HX{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+ZnX_{2}} }
2. 氫化鋁鋰(LiAlH4 ) 或 硼氫化鈉(NaBH4 ) ：[ 19]
4
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
2
X
+
L
i
A
l
H
4
→
4
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
A
l
X
3
+
L
i
X
{\displaystyle \mathrm {4CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}X+LiAlH_{4}{\xrightarrow {}}4CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+AlX_{3}+LiX} }
或
4
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
X
C
H
3
+
Z
n
+
H
X
+
L
i
A
l
H
4
→
4
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
A
l
X
3
+
L
i
X
{\displaystyle \mathrm {4CH_{3}CH_{2}CH(CH_{3})CHXCH_{3}+Zn+HX+LiAlH_{4}{\xrightarrow {}}4CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+AlX_{3}+LiX} }
或
4
C
H
3
C
H
2
C
X
(
C
H
3
)
C
H
2
C
H
3
+
Z
n
+
H
X
+
L
i
A
l
H
4
→
4
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
A
l
X
3
+
L
i
X
{\displaystyle \mathrm {4CH_{3}CH_{2}CX(CH_{3})CH_{2}CH_{3}+Zn+HX+LiAlH_{4}{\xrightarrow {}}4CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+AlX_{3}+LiX} }
或
4
(
C
H
3
C
H
2
)
2
C
H
C
H
2
X
+
Z
n
+
H
X
+
L
i
A
l
H
4
→
4
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
A
l
X
3
+
L
i
X
{\displaystyle \mathrm {4(CH_{3}CH_{2})_{2}CHCH_{2}X+Zn+HX+LiAlH_{4}{\xrightarrow {}}4CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+AlX_{3}+LiX} }
3. 使用碘化氫(HI) 還原烷基碘 ：[ 20]
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
2
I
+
H
I
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
I
2
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}I+HI{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+I_{2}} }
或
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
I
C
H
3
+
H
I
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
I
2
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CHICH_{3}+HI{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+I_{2}} }
或
C
H
3
C
H
2
C
I
(
C
H
3
)
C
H
2
C
H
3
+
H
I
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
I
2
{\displaystyle \mathrm {CH_{3}CH_{2}CI(CH_{3})CH_{2}CH_{3}+HI{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+I_{2}} }
或
(
C
H
3
C
H
2
)
2
C
H
C
H
2
I
+
H
I
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
I
2
{\displaystyle \mathrm {(CH_{3}CH_{2})_{2}CHCH_{2}I+HI{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+I_{2}} }
4. 使用甲矽烷(SiH4) 中還原烷基鹵化物 ，在三氟化硼 的催化下製備丁烷 ：[ 21]
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
2
X
+
S
i
H
4
→
B
F
3
C
H
3
C
H
2
C
H
2
C
H
(
C
H
3
)
2
+
S
i
H
3
X
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}X+SiH_{4}{\xrightarrow {BF_{3}}}CH_{3}CH_{2}CH_{2}CH(CH_{3})_{2}+SiH_{3}X} }
或
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
X
C
H
3
+
S
i
H
4
→
B
F
3
C
H
3
C
H
2
C
H
2
C
H
(
C
H
3
)
2
+
S
i
H
3
X
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CHXCH_{3}+SiH_{4}{\xrightarrow {BF_{3}}}CH_{3}CH_{2}CH_{2}CH(CH_{3})_{2}+SiH_{3}X} }
或
C
H
3
C
H
2
C
X
(
C
H
3
)
C
H
2
C
H
3
+
S
i
H
4
→
B
F
3
C
H
3
C
H
2
C
H
2
C
H
(
C
H
3
)
2
+
S
i
H
3
X
{\displaystyle \mathrm {CH_{3}CH_{2}CX(CH_{3})CH_{2}CH_{3}+SiH_{4}{\xrightarrow {BF_{3}}}CH_{3}CH_{2}CH_{2}CH(CH_{3})_{2}+SiH_{3}X} }
或
(
C
H
3
C
H
2
)
2
C
H
C
H
2
X
+
S
i
H
4
→
B
F
3
C
H
3
C
H
2
C
H
2
C
H
(
C
H
3
)
2
+
S
i
H
3
X
{\displaystyle \mathrm {(CH_{3}CH_{2})_{2}CHCH_{2}X+SiH_{4}{\xrightarrow {BF_{3}}}CH_{3}CH_{2}CH_{2}CH(CH_{3})_{2}+SiH_{3}X} }
5. 使用烷基錫烷 還原烷基鹵化物 ：[ 22]
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
2
X
+
R
S
n
H
3
→
C
H
3
C
H
2
C
H
2
C
H
(
C
H
3
)
2
+
R
S
n
H
2
X
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}X+RSnH_{3}{\xrightarrow {}}CH_{3}CH_{2}CH_{2}CH(CH_{3})_{2}+RSnH_{2}X} }
或
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
X
C
H
3
+
R
S
n
H
3
→
C
H
3
C
H
2
C
H
2
C
H
(
C
H
3
)
2
+
R
S
n
H
2
X
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CHXCH_{3}+RSnH_{3}{\xrightarrow {}}CH_{3}CH_{2}CH_{2}CH(CH_{3})_{2}+RSnH_{2}X} }
或
C
H
3
C
H
2
C
X
(
C
H
3
)
C
H
2
C
H
3
+
R
S
n
H
3
→
C
H
3
C
H
2
C
H
2
C
H
(
C
H
3
)
2
+
R
S
n
H
2
X
{\displaystyle \mathrm {CH_{3}CH_{2}CX(CH_{3})CH_{2}CH_{3}+RSnH_{3}{\xrightarrow {}}CH_{3}CH_{2}CH_{2}CH(CH_{3})_{2}+RSnH_{2}X} }
或
(
C
H
3
C
H
2
)
2
C
H
C
H
2
X
+
R
S
n
H
3
→
C
H
3
C
H
2
C
H
2
C
H
(
C
H
3
)
2
+
R
S
n
H
2
X
{\displaystyle \mathrm {(CH_{3}CH_{2})_{2}CHCH_{2}X+RSnH_{3}{\xrightarrow {}}CH_{3}CH_{2}CH_{2}CH(CH_{3})_{2}+RSnH_{2}X} }
6.金屬 的還原，得到水解 的有機金屬化合物 ：
使用鋰(Li) ：[ 23]
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
2
X
+
2
L
i
→
−
10
o
C
|
E
t
2
O
|
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
2
L
i
+
L
i
X
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}X+2Li{\xrightarrow[{-10^{o}C}]{|Et_{2}O|}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}Li+LiX} }
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
2
L
i
+
H
2
O
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
L
i
O
H
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}Li+H_{2}O{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+LiOH} }
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
X
C
H
3
+
2
L
i
→
−
10
o
C
|
E
t
2
O
|
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
L
i
C
H
3
+
L
i
X
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CHXCH_{3}+2Li{\xrightarrow[{-10^{o}C}]{|Et_{2}O|}}CH_{3}CH_{2}CH(CH_{3})CHLiCH_{3}+LiX} }
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
L
i
C
H
3
+
H
2
O
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
L
i
O
H
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CHLiCH_{3}+H_{2}O{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+LiOH} }
C
H
3
C
H
2
C
X
(
C
H
3
)
C
H
2
C
H
3
+
2
L
i
→
−
10
o
C
|
E
t
2
O
|
C
H
3
C
H
2
C
L
i
(
C
H
3
)
C
H
2
C
H
3
+
L
i
X
{\displaystyle \mathrm {CH_{3}CH_{2}CX(CH_{3})CH_{2}CH_{3}+2Li{\xrightarrow[{-10^{o}C}]{|Et_{2}O|}}CH_{3}CH_{2}CLi(CH_{3})CH_{2}CH_{3}+LiX} }
C
H
3
C
H
2
C
L
i
(
C
H
3
)
C
H
2
C
H
3
+
H
2
O
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
L
i
O
H
{\displaystyle \mathrm {CH_{3}CH_{2}CLi(CH_{3})CH_{2}CH_{3}+H_{2}O{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+LiOH} }
(
C
H
3
C
H
2
)
2
C
H
C
H
2
X
+
2
L
i
→
−
10
o
C
|
E
t
2
O
|
(
C
H
3
C
H
2
)
2
C
H
C
H
2
L
i
+
L
i
X
{\displaystyle \mathrm {(CH_{3}CH_{2})_{2}CHCH_{2}X+2Li{\xrightarrow[{-10^{o}C}]{|Et_{2}O|}}(CH_{3}CH_{2})_{2}CHCH_{2}Li+LiX} }
(
C
H
3
C
H
2
)
2
C
H
C
H
2
L
i
+
H
2
O
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
L
i
O
H
{\displaystyle \mathrm {(CH_{3}CH_{2})_{2}CHCH_{2}Li+H_{2}O{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+LiOH} }
使用鎂(Mg) ：[ 24]
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
2
X
+
M
g
→
|
E
t
2
O
|
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
2
M
g
X
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}X+Mg{\xrightarrow {|Et_{2}O|}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}MgX} }
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
2
M
g
X
+
H
2
O
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
M
g
(
O
H
)
X
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}MgX+H_{2}O{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+Mg(OH)X} }
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
X
C
H
3
+
M
g
→
|
E
t
2
O
|
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
M
g
X
C
H
3
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CHXCH_{3}+Mg{\xrightarrow {|Et_{2}O|}}CH_{3}CH_{2}CH(CH_{3})CHMgXCH_{3}} }
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
M
g
X
C
H
3
+
H
2
O
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
M
g
(
O
H
)
X
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CHMgXCH_{3}+H_{2}O{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+Mg(OH)X} }
C
H
3
C
H
2
C
X
(
C
H
3
)
C
H
2
C
H
3
+
M
g
→
|
E
t
2
O
|
C
H
3
C
H
2
C
M
g
X
(
C
H
3
)
C
H
2
C
H
3
{\displaystyle \mathrm {CH_{3}CH_{2}CX(CH_{3})CH_{2}CH_{3}+Mg{\xrightarrow {|Et_{2}O|}}CH_{3}CH_{2}CMgX(CH_{3})CH_{2}CH_{3}} }
C
H
3
C
H
2
C
M
g
X
(
C
H
3
)
C
H
2
C
H
3
+
H
2
O
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
M
g
(
O
H
)
X
{\displaystyle \mathrm {CH_{3}CH_{2}CMgX(CH_{3})CH_{2}CH_{3}+H_{2}O{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+Mg(OH)X} }
(
C
H
3
C
H
2
)
2
C
H
C
H
2
X
+
M
g
→
|
E
t
2
O
|
(
C
H
3
C
H
2
)
2
C
H
C
H
2
M
g
X
{\displaystyle \mathrm {(CH_{3}CH_{2})_{2}CHCH_{2}X+Mg{\xrightarrow {|Et_{2}O|}}(CH_{3}CH_{2})_{2}CHCH_{2}MgX} }
(
C
H
3
C
H
2
)
2
C
H
C
H
2
M
g
X
+
H
2
O
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
M
g
(
O
H
)
X
{\displaystyle \mathrm {(CH_{3}CH_{2})_{2}CHCH_{2}MgX+H_{2}O{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+Mg(OH)X} }
1. 3-甲基-1-戊烯 ：[ 25]
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
=
C
H
2
+
H
2
→
N
i
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH=CH_{2}+H_{2}{\xrightarrow {Ni}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}} }
2. 3-甲基-2-戊烯 ：[ 25]
C
H
3
C
H
2
C
(
C
H
3
)
=
C
H
C
H
3
+
H
2
→
N
i
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
{\displaystyle \mathrm {CH_{3}CH_{2}C(CH_{3})=CHCH_{3}+H_{2}{\xrightarrow {Ni}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}} }
3. 2-乙基-1-丁烯 ：[ 25]
(
C
H
3
C
H
2
)
2
C
=
C
H
2
+
H
2
→
N
i
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
{\displaystyle \mathrm {(CH_{3}CH_{2})_{2}C=CH_{2}+H_{2}{\xrightarrow {Ni}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}} }
4. 3-甲基-1,2-戊二烯 ：[ 25]
C
H
3
C
H
2
C
(
C
H
3
)
=
C
=
C
H
2
+
2
H
2
→
N
i
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
{\displaystyle \mathrm {CH_{3}CH_{2}C(CH_{3})=C=CH_{2}+2H_{2}{\xrightarrow {Ni}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}} }
5. 3-甲基-1,3-戊二烯 ：[ 25]
C
H
3
C
H
=
C
(
C
H
3
)
C
H
=
C
H
2
+
2
H
2
→
N
i
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
{\displaystyle \mathrm {CH_{3}CH=C(CH_{3})CH=CH_{2}+2H_{2}{\xrightarrow {Ni}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}} }
6. 3-甲基-1,4-戊二烯 ：[ 25]
C
H
2
=
C
H
C
H
(
C
H
3
)
C
H
=
C
H
2
+
2
H
2
→
N
i
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
{\displaystyle \mathrm {CH_{2}=CHCH(CH_{3})CH=CH_{2}+2H_{2}{\xrightarrow {Ni}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}} }
7. 3-甲基戊烷-1 ：[ 26]
C
H
3
C
2
H
C
H
(
C
H
3
)
C
≡
C
H
+
2
H
2
→
N
i
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
{\displaystyle \mathrm {CH_{3}C_{2}HCH(CH_{3})C\equiv CH+2H_{2}{\xrightarrow {Ni}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}} }
8. 3-甲基-1,2,4-戊二烯 ：[ 25]
C
H
2
=
C
H
C
(
C
H
3
)
=
C
=
C
H
2
+
3
H
2
→
N
i
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
{\displaystyle \mathrm {CH_{2}=CHC(CH_{3})=C=CH_{2}+3H_{2}{\xrightarrow {Ni}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}} }
9. 3-甲基-4-戊烯-2-炔 ：[ 25] [ 26]
C
H
3
C
H
=
C
(
C
H
3
)
C
≡
C
H
+
3
H
2
→
N
i
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
{\displaystyle \mathrm {CH_{3}CH=C(CH_{3})C\equiv CH+3H_{2}{\xrightarrow {Ni}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}} }
10. 3-甲基-4-戊烯-1-炔 ：[ 25] [ 26]
C
H
2
=
C
H
C
H
(
C
H
3
)
C
≡
C
H
+
3
H
2
→
N
i
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
{\displaystyle \mathrm {CH_{2}=CHCH(CH_{3})C\equiv CH+3H_{2}{\xrightarrow {Ni}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}} }
3-甲基戊醛 ：
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
O
+
N
H
2
N
H
2
→
K
O
H
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
N
2
+
H
2
O
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CHO+NH_{2}NH_{2}{\xrightarrow {KOH}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+N_{2}+H_{2}O} }
甲基丁醛 ：
C
H
3
C
H
2
C
H
(
C
H
2
C
H
3
)
C
H
O
+
N
H
2
N
H
2
→
K
O
H
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
N
2
+
H
2
O
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{2}CH_{3})CHO+NH_{2}NH_{2}{\xrightarrow {KOH}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+N_{2}+H_{2}O} }
3-甲基戊酮
C
H
3
C
H
2
C
H
(
C
H
3
)
C
O
C
H
3
+
2
Z
n
+
2
H
C
l
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
Z
n
C
l
2
+
Z
n
O
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})COCH_{3}+2Zn+2HCl{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+ZnCl_{2}+ZnO} }
1.還原硫醇 可以產生3-甲基戊烷 。
例如 通過還原 3-甲基-1-戊硫醇 （雷尼鎳 催化 ）：[ 29]
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
2
S
H
+
H
2
→
N
i
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
H
2
S
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}SH+H_{2}{\xrightarrow {Ni}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+H_{2}S} }
2.還原硫酯可以產生3-甲基戊烷..
例如 通過還原 二（3-甲基戊基）硫醚 （雷尼鎳 催化 ）：[ 30]
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
2
S
C
H
2
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
2
H
2
→
N
i
2
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
H
2
S
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}SCH_{2}CH_{2}CH(CH_{3})CH_{2}CH_{3}+2H_{2}{\xrightarrow {Ni}}2CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+H_{2}S} }
加熱鹼性 的 4-甲基己酸 溶液 [CH3 CH2 CH(CH3 )CH2 CH2 COOH] [ 31]
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
2
C
O
O
H
+
N
a
O
H
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
2
C
O
O
N
a
+
H
2
O
→
4
C
H
3
C
H
2
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
N
a
H
C
O
3
→
△
C
H
3
C
H
2
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
N
a
O
H
+
C
O
2
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}COOH+NaOH{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}COONa+H_{2}O{\xrightarrow {\mathcal {4}}}CH_{3}CH_{2}CH_{2}CH(CH_{3})CH_{2}CH_{3}+NaHCO_{3}{\xrightarrow {\triangle }}CH_{3}CH_{2}CH_{2}CH(CH_{3})CH_{2}CH_{3}+NaOH+CO_{2}} }
或 2,3-二甲基戊酸 [CH3 CH2 CH(CH3 )CH(CH3 )COOH]
C
H
3
C
H
2
C
(
C
H
3
)
(
C
H
2
C
H
3
)
C
O
O
H
+
N
a
O
H
→
C
H
3
C
H
2
C
(
C
H
3
)
(
C
H
2
C
H
3
)
C
O
O
N
a
+
H
2
O
→
4
C
H
3
C
H
2
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
N
a
H
C
O
3
→
△
C
H
3
C
H
2
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
N
a
O
H
+
C
O
2
{\displaystyle \mathrm {CH_{3}CH_{2}C(CH_{3})(CH_{2}CH_{3})COOH+NaOH{\xrightarrow {}}CH_{3}CH_{2}C(CH_{3})(CH_{2}CH_{3})COONa+H_{2}O{\xrightarrow {\mathcal {4}}}CH_{3}CH_{2}CH_{2}CH(CH_{3})CH_{2}CH_{3}+NaHCO_{3}{\xrightarrow {\triangle }}CH_{3}CH_{2}CH_{2}CH(CH_{3})CH_{2}CH_{3}+NaOH+CO_{2}} }
或 2-乙基-2-甲基丁酸 [CH3 CH2 C(CH3 )(CH2 CH3 )COOH]
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
(
C
H
3
)
C
O
O
H
+
N
a
O
H
→
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
(
C
H
3
)
C
O
O
N
a
+
H
2
O
→
4
C
H
3
C
H
2
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
N
a
H
C
O
3
→
△
C
H
3
C
H
2
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
N
a
O
H
+
C
O
2
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH(CH_{3})COOH+NaOH{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH(CH_{3})COONa+H_{2}O{\xrightarrow {\mathcal {4}}}CH_{3}CH_{2}CH_{2}CH(CH_{3})CH_{2}CH_{3}+NaHCO_{3}{\xrightarrow {\triangle }}CH_{3}CH_{2}CH_{2}CH(CH_{3})CH_{2}CH_{3}+NaOH+CO_{2}} }
或 3-乙基戊酸 [(CH3 )2 CHCH2 CH2 COOH]
(
C
H
3
C
H
2
)
2
C
H
C
H
2
C
O
O
H
+
N
a
O
H
→
C
H
3
C
H
2
)
2
C
H
C
H
2
C
O
O
N
a
+
H
2
O
→
4
C
H
3
C
H
2
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
N
a
H
C
O
3
→
△
C
H
3
C
H
2
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
N
a
O
H
+
C
O
2
{\displaystyle \mathrm {(CH_{3}CH_{2})_{2}CHCH_{2}COOH+NaOH{\xrightarrow {}}CH_{3}CH_{2})_{2}CHCH_{2}COONa+H_{2}O{\xrightarrow {\mathcal {4}}}CH_{3}CH_{2}CH_{2}CH(CH_{3})CH_{2}CH_{3}+NaHCO_{3}{\xrightarrow {\triangle }}CH_{3}CH_{2}CH_{2}CH(CH_{3})CH_{2}CH_{3}+NaOH+CO_{2}} }
1.完全燃燒 ：就像所有的烷烴 一樣，3-甲基戊烷與過量的氧氣 燃燒 ，產生二氧化碳 和水 ：[ 32]
2
C
6
H
14
+
19
O
2
→
△
12
C
O
2
+
14
H
2
O
+
8343
k
J
{\displaystyle \mathrm {2C_{6}H_{14}+19O_{2}{\xrightarrow {\triangle }}12CO_{2}+14H_{2}O+8343kJ} }
2.水煤氣 ：
C
6
H
14
+
6
H
2
O
→
700
−
1100
o
C
N
i
6
C
O
+
14
H
2
{\displaystyle \mathrm {C_{6}H_{14}+6H_{2}O{\xrightarrow[{700-1100^{o}C}]{Ni}}6CO+14H_{2}} }
3.催化氧化 的主要產物為3-甲基戊醇-3 ：
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
1
2
O
2
→
△
C
u
C
H
3
C
H
2
C
(
O
H
)
(
C
H
3
)
C
H
2
C
H
3
{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+{\frac {1}{2}}O_{2}{\xrightarrow[{\triangle }]{Cu}}CH_{3}CH_{2}C(OH)(CH_{3})CH_{2}CH_{3}} }
4.使用高錳酸鉀(KMnO4 ) 氧化 的產物為3-甲基戊醇-3 ：
3
C
H
3
C
H
2
C
H
(
C
H
3
)
C
H
2
C
H
3
+
2
K
M
n
O
4
+
H
2
S
O
4
→
C
H
3
C
H
2
C
(
O
H
)
(
C
H
3
)
C
H
2
C
H
3
+
2
M
n
O
2
+
K
2
S
O
4
+
H
2
O
{\displaystyle \mathrm {3CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+2KMnO_{4}+H_{2}SO_{4}{\xrightarrow {}}CH_{3}CH_{2}C(OH)(CH_{3})CH_{2}CH_{3}+2MnO_{2}+K_{2}SO_{4}+H_{2}O} }
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{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+X_{2}{\xrightarrow[{\triangle }]{UV}}aCH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}X+bCH_{3}CH_{2}CH(CH_{3})CHXCH_{3}+cCH_{3}CH_{2}CX(CH_{3})CH_{2}CH_{3}+dCH_{3}CH_{2}CH(CH_{2}X)CH_{2}CH_{3}+HX} }
3 CH2 CH(CH3 )CH2 CH3 的氯化分析：參見:統計學
1.發生：自由基 生產
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{\displaystyle \mathrm {Cl_{2}{\xrightarrow[{\triangle }]{UV}}2Cl^{\bullet }-239kJ} }
所需要的能量 從紫外光(UV) 或熱(D) 吸收
2.擴散 ：消耗舊自由基，形成新的自由基
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{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+Cl^{\bullet }{\xrightarrow {}}0,21CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}^{\bullet }+0,52CH_{3}CH_{2}CH(CH_{3})CH^{\bullet }CH_{3}+0,17CH_{3}CH_{2}C^{\bullet }(CH_{3})CH_{2}CH_{3}+0,1CH_{3}CH_{2}CH(CH_{2}^{\bullet })CH_{2}CH_{3}+HCl+14kJ} }
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{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}^{\bullet }+Cl_{2}{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}Cl+Cl^{\bullet }+100kJ} }
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{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH^{\bullet }CH_{3}+Cl_{2}{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH(Cl)CH_{3}+Cl^{\bullet }+100kJ} }
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{\displaystyle \mathrm {CH_{3}CH_{2}C^{\bullet }(CH_{3})CH_{2}CH_{3}+Cl_{2}{\xrightarrow {}}CH_{3}CH_{2}C(Cl)(CH_{3})CH_{2}CH_{3}+Cl^{\bullet }+100kJ} }
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{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{2}^{\bullet })CH_{2}CH_{3}+Cl_{2}{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{2}Cl)CH_{2}CH_{3}+Cl^{\bullet }+100kJ} }
3.終止：自由基 在罕見的情況下消耗[ 37]
2
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{\displaystyle \mathrm {2Cl^{\bullet }{\xrightarrow {}}Cl_{2}+239kJ} }
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{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}^{\bullet }+Cl^{\bullet }{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}Cl+339kJ} }
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{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH^{\bullet }CH_{3}+Cl^{\bullet }{\xrightarrow {}}(CH_{3})_{2}CHCH_{2}CH(Cl)CH_{3}+339kJ} }
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{\displaystyle \mathrm {CH_{3}CH_{2}C^{\bullet }(CH_{3})CH_{2}CH_{3}+Cl^{\bullet }{\xrightarrow {}}CH_{3}CH_{2}C(Cl)(CH_{3})CH_{2}CH_{3}+339kJ} }
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{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{2}^{\bullet })CH_{2}CH_{3}+Cl^{\bullet }{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{2}Cl)CH_{2}CH_{3}+339kJ} }
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{\displaystyle \mathrm {2CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}^{\bullet }{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}CH_{2}CH_{2}CH(CH_{3})CH_{2}CH_{3}+347kJ} }
2
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{\displaystyle \mathrm {2CH_{3}CH_{2}CH(CH_{3})CH^{\bullet }CH_{3}{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{3})CH(CH_{3})CH(CH_{3})CH(CH_{3})CH_{2}CH_{3}+347kJ} }
2
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{\displaystyle \mathrm {2CH_{3}CH_{2}C^{\bullet }(CH_{3})CH_{2}CH_{3}{\xrightarrow {}}(CH_{3}CH_{2})_{2}C(CH_{3})C(CH_{3})(CH_{3}CH_{2})_{2}+347kJ} }
[ 38]
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{\displaystyle \mathrm {2CH_{3}CH_{2}CH(CH_{2}^{\bullet })CH_{2}CH_{3}{\xrightarrow {}}CH_{3}CH_{2}CH(CH_{2}CH_{3})CH_{2}CH_{2}CH(CH_{2}CH_{3})CH_{2}CH_{3}+347kJ} }
然而，在製造單鹵化物時，實際上難以停止反應，如果使用等摩爾量的CH3 CH2 CH(CH3 )CH2 CH3 和X2 則將產生CH3 CH2 CH(CH3 )CH2 CH3 的全部鹵素衍生物的混合物
如果使用過量的CH3 CH2 CH(CH3 )CH2 CH3 ，則單一衍生物的產率，由於與自由基遇到和X的概率相關的CH2 CH2 CH(CH3 )CH2 CH3 (CH3 )2 的統計概率的增加而大大增加
導致剩餘的X衍生物的生產 碳烯 （例如[：CH2]）反應是極少消耗的，可以插入C-H鍵。 例如 :[ 39]
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{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+CH_{3}Cl+KOH{\xrightarrow {}}{\frac {3}{7}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}CH_{3}+{\frac {2}{7}}CH_{3}CH_{2}CH(CH_{3})CH(CH_{3})_{2}+{\frac {1}{14}}CH_{3}CH_{2}C(CH_{3})_{2}CH_{2}CH_{3}+{\frac {2}{7}}CH_{3}CH_{2}CH(CH_{2}CH_{3})CH_{2}CH_{3}+KCl+H_{2}O} }
碳烯在六鍵 CH-1,5- 2 -h：6
碳烯在四鍵 2,4-CH-H：4
插鍵CH：1
三個插入物（3）鏈路CH-1' 2 -H）：4。
因此，存在3-甲基己烷（〜43％），2,3-二甲基戊烷（〜29％），3,3-二甲基戊烷（〜7％）和乙基戊烷（-29％）的混合物
與硝酸(HNO3 ) 的蒸氣反應：[ 40]
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{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+HNO_{3}{\xrightarrow {\triangle }}aCH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}NO_{2}+bCH_{3}CH_{2}CH(CH_{3})CH(NO_{2})CH_{3}+cCH_{3}CH_{2}C(NO_{2})(CH_{3})CH_{2}CH_{3}+dCH_{3}CH_{2}CH(CH_{2}NO_{2})CH_{2}CH_{3}+H_{2}O} }
其中0 <A，B，C，D <1，A + B + C + D = 1
3-甲基戊烷可以在 (CH3 CH2 )2 Cs- (CH3 )-Hs+ 的含義內產生多個鍵合反應。如：[ 41]
(
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{\displaystyle \mathrm {(CH_{3}CH_{2})_{2}CHCH_{3}+RCH=CH_{2}{\xrightarrow[{0^{o}C}]{HF}}(CH_{3}CH_{2})_{2}C(CH_{3})CH(R)CH_{3}} }
2-甲基戊烷可經催化異構化變成己烷 ，2,2-二甲基丁烷(新己烷) 和2,3-二甲基丁烷 ：
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{\displaystyle \mathrm {CH_{3}CH_{2}CH_{2}CH_{2}CH_{2}CH_{3}{\stackrel {AlCl_{3}}{\overrightarrow {\longleftarrow }}}CH_{3}CH_{2}CH_{2}CH(CH_{3})_{2}{\stackrel {AlCl_{3}}{\overrightarrow {\longleftarrow }}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}{\stackrel {AlCl_{3}}{\overrightarrow {\longleftarrow }}}(CH_{3})_{4}C{\stackrel {AlCl_{3}}{\overrightarrow {\longleftarrow }}}CH_{3}CH(CH_{3})CH(CH_{3})CH_{2}CH_{3}} }
![{\displaystyle \mathrm {CH_{3}CH_{2}CH_{2}CH_{3}+C_{2}H_{4}{\xrightarrow[{400^{o}C,200bar}]{PCl_{3}}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}} }](https://wikimedia.org/api/rest_v1/media/math/render/svg/279f4043380cba97f2b53b52c307db19ff96672f)
![{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}X+2Li{\xrightarrow[{-10^{o}C}]{|Et_{2}O|}}CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}Li+LiX} }](https://wikimedia.org/api/rest_v1/media/math/render/svg/35a01d618e6db233645a6620125e2bdbff5ac755)
![{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CHXCH_{3}+2Li{\xrightarrow[{-10^{o}C}]{|Et_{2}O|}}CH_{3}CH_{2}CH(CH_{3})CHLiCH_{3}+LiX} }](https://wikimedia.org/api/rest_v1/media/math/render/svg/7acf32fe22be182bd91b84ca9099cd6a14c9a940)
![{\displaystyle \mathrm {CH_{3}CH_{2}CX(CH_{3})CH_{2}CH_{3}+2Li{\xrightarrow[{-10^{o}C}]{|Et_{2}O|}}CH_{3}CH_{2}CLi(CH_{3})CH_{2}CH_{3}+LiX} }](https://wikimedia.org/api/rest_v1/media/math/render/svg/85d39372d9d6328522ca5a237f130e7b184d6f9e)
![{\displaystyle \mathrm {(CH_{3}CH_{2})_{2}CHCH_{2}X+2Li{\xrightarrow[{-10^{o}C}]{|Et_{2}O|}}(CH_{3}CH_{2})_{2}CHCH_{2}Li+LiX} }](https://wikimedia.org/api/rest_v1/media/math/render/svg/4a573289597ce5fa285aba6f5e302edd128267d6)
![{\displaystyle \mathrm {C_{6}H_{14}+6H_{2}O{\xrightarrow[{700-1100^{o}C}]{Ni}}6CO+14H_{2}} }](https://wikimedia.org/api/rest_v1/media/math/render/svg/bc614cb06d25d60002976e6ab05e54a5f6b11e11)
![{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+{\frac {1}{2}}O_{2}{\xrightarrow[{\triangle }]{Cu}}CH_{3}CH_{2}C(OH)(CH_{3})CH_{2}CH_{3}} }](https://wikimedia.org/api/rest_v1/media/math/render/svg/a4265be986ab6c8fb4319bf6e77ddc2749322b63)
![{\displaystyle \mathrm {CH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{3}+X_{2}{\xrightarrow[{\triangle }]{UV}}aCH_{3}CH_{2}CH(CH_{3})CH_{2}CH_{2}X+bCH_{3}CH_{2}CH(CH_{3})CHXCH_{3}+cCH_{3}CH_{2}CX(CH_{3})CH_{2}CH_{3}+dCH_{3}CH_{2}CH(CH_{2}X)CH_{2}CH_{3}+HX} }](https://wikimedia.org/api/rest_v1/media/math/render/svg/a45033260e6d448a148524da1549c2330221fcb5)
![{\displaystyle \mathrm {Cl_{2}{\xrightarrow[{\triangle }]{UV}}2Cl^{\bullet }-239kJ} }](https://wikimedia.org/api/rest_v1/media/math/render/svg/73fe9c8e7397e9e50d5b5a7ea91a25e26bed2f96)
![{\displaystyle \mathrm {(CH_{3}CH_{2})_{2}CHCH_{3}+RCH=CH_{2}{\xrightarrow[{0^{o}C}]{HF}}(CH_{3}CH_{2})_{2}C(CH_{3})CH(R)CH_{3}} }](https://wikimedia.org/api/rest_v1/media/math/render/svg/5f2c4d492968512540fac1463736dd4a348634ce)
