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有機反応
アルコールのカルボン酸への酸化 (クロム(VI)化合物)
アルコールのカルボン酸への酸化 (クロム(VI)化合物)
アルコールのカルボン酸への酸化 (クロム(VI)化合物)
アルコール
還元剤
+
クロム(VI)化合物
酸化剤
+
H
+
非酸化還元剤
⟶
カルボン酸
酸化生成物
+
Cr
3+
還元生成物
+
陽イオン
(非酸化還元生成物)
+
H
2
O
非酸化還元生成物
「アルコールのカルボン酸への酸化 (クロム(VI)化合物)」の一覧
120
件中の
1–100
件
<<
<
/ 2
>
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3
CH
3
OH
+
4
CrO
3
+
12
H
+
⟶
3
HCOOH
+
4
Cr
3+
+
9
H
2
O
3
CH
3
OH
+
2
H
2
Cr
2
O
7
+
12
H
+
⟶
3
HCOOH
+
4
Cr
3+
+
11
H
2
O
3
CH
3
OH
+
4
H
2
CrO
4
+
12
H
+
⟶
3
HCOOH
+
4
Cr
3+
+
13
H
2
O
3
C
2
H
5
OH
+
4
CrO
3
+
12
H
+
⟶
3
CH
3
COOH
+
4
Cr
3+
+
9
H
2
O
3
C
2
H
5
OH
+
2
H
2
Cr
2
O
7
+
12
H
+
⟶
3
CH
3
COOH
+
4
Cr
3+
+
11
H
2
O
3
C
2
H
5
OH
+
4
H
2
CrO
4
+
12
H
+
⟶
3
CH
3
COOH
+
4
Cr
3+
+
13
H
2
O
3
C
3
H
7
OH
+
4
CrO
3
+
12
H
+
⟶
3
C
2
H
5
COOH
+
4
Cr
3+
+
9
H
2
O
3
C
3
H
7
OH
+
2
H
2
Cr
2
O
7
+
12
H
+
⟶
3
C
2
H
5
COOH
+
4
Cr
3+
+
11
H
2
O
3
C
3
H
7
OH
+
4
H
2
CrO
4
+
12
H
+
⟶
3
C
2
H
5
COOH
+
4
Cr
3+
+
13
H
2
O
3
C
4
H
9
OH
+
4
CrO
3
+
12
H
+
⟶
3
C
3
H
7
COOH
+
4
Cr
3+
+
9
H
2
O
3
C
4
H
9
OH
+
2
H
2
Cr
2
O
7
+
12
H
+
⟶
3
C
3
H
7
COOH
+
4
Cr
3+
+
11
H
2
O
3
C
4
H
9
OH
+
4
H
2
CrO
4
+
12
H
+
⟶
3
C
3
H
7
COOH
+
4
Cr
3+
+
13
H
2
O
3
C
5
H
11
OH
+
4
CrO
3
+
12
H
+
⟶
3
C
4
H
9
COOH
+
4
Cr
3+
+
9
H
2
O
3
C
5
H
11
OH
+
2
H
2
Cr
2
O
7
+
12
H
+
⟶
3
C
4
H
9
COOH
+
4
Cr
3+
+
11
H
2
O
3
C
5
H
11
OH
+
4
H
2
CrO
4
+
12
H
+
⟶
3
C
4
H
9
COOH
+
4
Cr
3+
+
13
H
2
O
3
C
6
H
13
OH
+
4
CrO
3
+
12
H
+
⟶
3
C
5
H
11
COOH
+
4
Cr
3+
+
9
H
2
O
3
C
6
H
13
OH
+
2
H
2
Cr
2
O
7
+
12
H
+
⟶
3
C
5
H
11
COOH
+
4
Cr
3+
+
11
H
2
O
3
C
6
H
13
OH
+
4
H
2
CrO
4
+
12
H
+
⟶
3
C
5
H
11
COOH
+
4
Cr
3+
+
13
H
2
O
3
C
7
H
15
OH
+
4
CrO
3
+
12
H
+
⟶
3
C
6
H
13
COOH
+
4
Cr
3+
+
9
H
2
O
3
C
7
H
15
OH
+
2
H
2
Cr
2
O
7
+
12
H
+
⟶
3
C
6
H
13
COOH
+
4
Cr
3+
+
11
H
2
O
3
C
7
H
15
OH
+
4
H
2
CrO
4
+
12
H
+
⟶
3
C
6
H
13
COOH
+
4
Cr
3+
+
13
H
2
O
3
C
8
H
17
OH
+
4
CrO
3
+
12
H
+
⟶
3
C
7
H
15
COOH
+
4
Cr
3+
+
9
H
2
O
3
C
8
H
17
OH
+
2
H
2
Cr
2
O
7
+
12
H
+
⟶
3
C
7
H
15
COOH
+
4
Cr
3+
+
11
H
2
O
3
C
8
H
17
OH
+
4
H
2
CrO
4
+
12
H
+
⟶
3
C
7
H
15
COOH
+
4
Cr
3+
+
13
H
2
O
3
C
9
H
19
OH
+
4
CrO
3
+
12
H
+
⟶
3
C
8
H
17
COOH
+
4
Cr
3+
+
9
H
2
O
3
C
9
H
19
OH
+
2
H
2
Cr
2
O
7
+
12
H
+
⟶
3
C
8
H
17
COOH
+
4
Cr
3+
+
11
H
2
O
3
C
9
H
19
OH
+
4
H
2
CrO
4
+
12
H
+
⟶
3
C
8
H
17
COOH
+
4
Cr
3+
+
13
H
2
O
3
C
10
H
21
OH
+
4
CrO
3
+
12
H
+
⟶
3
C
9
H
19
COOH
+
4
Cr
3+
+
9
H
2
O
3
C
10
H
21
OH
+
2
H
2
Cr
2
O
7
+
12
H
+
⟶
3
C
9
H
19
COOH
+
4
Cr
3+
+
11
H
2
O
3
C
10
H
21
OH
+
4
H
2
CrO
4
+
12
H
+
⟶
3
C
9
H
19
COOH
+
4
Cr
3+
+
13
H
2
O
3
C
11
H
23
OH
+
4
CrO
3
+
12
H
+
⟶
3
C
10
H
21
COOH
+
4
Cr
3+
+
9
H
2
O
3
C
11
H
23
OH
+
2
H
2
Cr
2
O
7
+
12
H
+
⟶
3
C
10
H
21
COOH
+
4
Cr
3+
+
11
H
2
O
3
C
11
H
23
OH
+
4
H
2
CrO
4
+
12
H
+
⟶
3
C
10
H
21
COOH
+
4
Cr
3+
+
13
H
2
O
3
C
12
H
25
OH
+
4
CrO
3
+
12
H
+
⟶
3
C
11
H
23
COOH
+
4
Cr
3+
+
9
H
2
O
3
C
12
H
25
OH
+
2
H
2
Cr
2
O
7
+
12
H
+
⟶
3
C
11
H
23
COOH
+
4
Cr
3+
+
11
H
2
O
3
C
12
H
25
OH
+
4
H
2
CrO
4
+
12
H
+
⟶
3
C
11
H
23
COOH
+
4
Cr
3+
+
13
H
2
O
3
CH
3
OH
+
2
Na
2
Cr
2
O
7
+
16
H
+
⟶
3
HCOOH
+
4
Cr
3+
+
4
Na
+
+
11
H
2
O
3
CH
3
OH
+
4
Na
2
CrO
4
+
20
H
+
⟶
3
HCOOH
+
4
Cr
3+
+
8
Na
+
+
13
H
2
O
3
C
2
H
5
OH
+
2
Na
2
Cr
2
O
7
+
16
H
+
⟶
3
CH
3
COOH
+
4
Cr
3+
+
4
Na
+
+
11
H
2
O
3
C
2
H
5
OH
+
4
Na
2
CrO
4
+
20
H
+
⟶
3
CH
3
COOH
+
4
Cr
3+
+
8
Na
+
+
13
H
2
O
3
CH
3
OH
+
2
K
2
Cr
2
O
7
+
16
H
+
⟶
3
HCOOH
+
4
Cr
3+
+
4
K
+
+
11
H
2
O
3
CH
3
OH
+
2
CaCr
2
O
7
+
16
H
+
⟶
3
HCOOH
+
4
Cr
3+
+
2
Ca
2+
+
11
H
2
O
3
C
2
H
5
OH
+
2
K
2
Cr
2
O
7
+
16
H
+
⟶
3
CH
3
COOH
+
4
Cr
3+
+
4
K
+
+
11
H
2
O
3
CH
3
OH
+
4
CaCrO
4
+
20
H
+
⟶
3
HCOOH
+
4
Cr
3+
+
4
Ca
2+
+
13
H
2
O
3
C
2
H
5
OH
+
2
CaCr
2
O
7
+
16
H
+
⟶
3
CH
3
COOH
+
4
Cr
3+
+
2
Ca
2+
+
11
H
2
O
3
C
2
H
5
OH
+
4
CaCrO
4
+
20
H
+
⟶
3
CH
3
COOH
+
4
Cr
3+
+
4
Ca
2+
+
13
H
2
O
3
C
3
H
7
OH
+
2
Na
2
Cr
2
O
7
+
16
H
+
⟶
3
C
2
H
5
COOH
+
4
Cr
3+
+
4
Na
+
+
11
H
2
O
3
C
3
H
7
OH
+
4
Na
2
CrO
4
+
20
H
+
⟶
3
C
2
H
5
COOH
+
4
Cr
3+
+
8
Na
+
+
13
H
2
O
3
C
4
H
9
OH
+
2
Na
2
Cr
2
O
7
+
16
H
+
⟶
3
C
3
H
7
COOH
+
4
Cr
3+
+
4
Na
+
+
11
H
2
O
3
C
4
H
9
OH
+
4
Na
2
CrO
4
+
20
H
+
⟶
3
C
3
H
7
COOH
+
4
Cr
3+
+
8
Na
+
+
13
H
2
O
3
C
5
H
11
OH
+
2
Na
2
Cr
2
O
7
+
16
H
+
⟶
3
C
4
H
9
COOH
+
4
Cr
3+
+
4
Na
+
+
11
H
2
O
3
C
5
H
11
OH
+
4
Na
2
CrO
4
+
20
H
+
⟶
3
C
4
H
9
COOH
+
4
Cr
3+
+
8
Na
+
+
13
H
2
O
3
C
6
H
13
OH
+
2
Na
2
Cr
2
O
7
+
16
H
+
⟶
3
C
5
H
11
COOH
+
4
Cr
3+
+
4
Na
+
+
11
H
2
O
3
C
6
H
13
OH
+
4
Na
2
CrO
4
+
20
H
+
⟶
3
C
5
H
11
COOH
+
4
Cr
3+
+
8
Na
+
+
13
H
2
O
3
C
7
H
15
OH
+
2
Na
2
Cr
2
O
7
+
16
H
+
⟶
3
C
6
H
13
COOH
+
4
Cr
3+
+
4
Na
+
+
11
H
2
O
3
C
7
H
15
OH
+
4
Na
2
CrO
4
+
20
H
+
⟶
3
C
6
H
13
COOH
+
4
Cr
3+
+
8
Na
+
+
13
H
2
O
3
C
8
H
17
OH
+
2
Na
2
Cr
2
O
7
+
16
H
+
⟶
3
C
7
H
15
COOH
+
4
Cr
3+
+
4
Na
+
+
11
H
2
O
3
C
8
H
17
OH
+
4
Na
2
CrO
4
+
20
H
+
⟶
3
C
7
H
15
COOH
+
4
Cr
3+
+
8
Na
+
+
13
H
2
O
3
C
9
H
19
OH
+
2
Na
2
Cr
2
O
7
+
16
H
+
⟶
3
C
8
H
17
COOH
+
4
Cr
3+
+
4
Na
+
+
11
H
2
O
3
C
9
H
19
OH
+
4
Na
2
CrO
4
+
20
H
+
⟶
3
C
8
H
17
COOH
+
4
Cr
3+
+
8
Na
+
+
13
H
2
O
3
C
10
H
21
OH
+
2
Na
2
Cr
2
O
7
+
16
H
+
⟶
3
C
9
H
19
COOH
+
4
Cr
3+
+
4
Na
+
+
11
H
2
O
3
C
10
H
21
OH
+
4
Na
2
CrO
4
+
20
H
+
⟶
3
C
9
H
19
COOH
+
4
Cr
3+
+
8
Na
+
+
13
H
2
O
3
C
11
H
23
OH
+
2
Na
2
Cr
2
O
7
+
16
H
+
⟶
3
C
10
H
21
COOH
+
4
Cr
3+
+
4
Na
+
+
11
H
2
O
3
C
11
H
23
OH
+
4
Na
2
CrO
4
+
20
H
+
⟶
3
C
10
H
21
COOH
+
4
Cr
3+
+
8
Na
+
+
13
H
2
O
3
C
12
H
25
OH
+
2
Na
2
Cr
2
O
7
+
16
H
+
⟶
3
C
11
H
23
COOH
+
4
Cr
3+
+
4
Na
+
+
11
H
2
O
3
C
12
H
25
OH
+
4
Na
2
CrO
4
+
20
H
+
⟶
3
C
11
H
23
COOH
+
4
Cr
3+
+
8
Na
+
+
13
H
2
O
3
C
3
H
7
OH
+
2
K
2
Cr
2
O
7
+
16
H
+
⟶
3
C
2
H
5
COOH
+
4
Cr
3+
+
4
K
+
+
11
H
2
O
3
C
3
H
7
OH
+
2
CaCr
2
O
7
+
16
H
+
⟶
3
C
2
H
5
COOH
+
4
Cr
3+
+
2
Ca
2+
+
11
H
2
O
3
C
4
H
9
OH
+
2
K
2
Cr
2
O
7
+
16
H
+
⟶
3
C
3
H
7
COOH
+
4
Cr
3+
+
4
K
+
+
11
H
2
O
3
C
3
H
7
OH
+
4
CaCrO
4
+
20
H
+
⟶
3
C
2
H
5
COOH
+
4
Cr
3+
+
4
Ca
2+
+
13
H
2
O
3
C
4
H
9
OH
+
2
CaCr
2
O
7
+
16
H
+
⟶
3
C
3
H
7
COOH
+
4
Cr
3+
+
2
Ca
2+
+
11
H
2
O
3
C
5
H
11
OH
+
2
K
2
Cr
2
O
7
+
16
H
+
⟶
3
C
4
H
9
COOH
+
4
Cr
3+
+
4
K
+
+
11
H
2
O
3
C
4
H
9
OH
+
4
CaCrO
4
+
20
H
+
⟶
3
C
3
H
7
COOH
+
4
Cr
3+
+
4
Ca
2+
+
13
H
2
O
3
C
5
H
11
OH
+
2
CaCr
2
O
7
+
16
H
+
⟶
3
C
4
H
9
COOH
+
4
Cr
3+
+
2
Ca
2+
+
11
H
2
O
3
C
6
H
13
OH
+
2
K
2
Cr
2
O
7
+
16
H
+
⟶
3
C
5
H
11
COOH
+
4
Cr
3+
+
4
K
+
+
11
H
2
O
3
C
5
H
11
OH
+
4
CaCrO
4
+
20
H
+
⟶
3
C
4
H
9
COOH
+
4
Cr
3+
+
4
Ca
2+
+
13
H
2
O
3
C
6
H
13
OH
+
2
CaCr
2
O
7
+
16
H
+
⟶
3
C
5
H
11
COOH
+
4
Cr
3+
+
2
Ca
2+
+
11
H
2
O
3
C
7
H
15
OH
+
2
K
2
Cr
2
O
7
+
16
H
+
⟶
3
C
6
H
13
COOH
+
4
Cr
3+
+
4
K
+
+
11
H
2
O
3
C
6
H
13
OH
+
4
CaCrO
4
+
20
H
+
⟶
3
C
5
H
11
COOH
+
4
Cr
3+
+
4
Ca
2+
+
13
H
2
O
3
C
7
H
15
OH
+
2
CaCr
2
O
7
+
16
H
+
⟶
3
C
6
H
13
COOH
+
4
Cr
3+
+
2
Ca
2+
+
11
H
2
O
3
C
8
H
17
OH
+
2
K
2
Cr
2
O
7
+
16
H
+
⟶
3
C
7
H
15
COOH
+
4
Cr
3+
+
4
K
+
+
11
H
2
O
3
C
7
H
15
OH
+
4
CaCrO
4
+
20
H
+
⟶
3
C
6
H
13
COOH
+
4
Cr
3+
+
4
Ca
2+
+
13
H
2
O
3
C
8
H
17
OH
+
2
CaCr
2
O
7
+
16
H
+
⟶
3
C
7
H
15
COOH
+
4
Cr
3+
+
2
Ca
2+
+
11
H
2
O
3
C
9
H
19
OH
+
2
K
2
Cr
2
O
7
+
16
H
+
⟶
3
C
8
H
17
COOH
+
4
Cr
3+
+
4
K
+
+
11
H
2
O
3
C
8
H
17
OH
+
4
CaCrO
4
+
20
H
+
⟶
3
C
7
H
15
COOH
+
4
Cr
3+
+
4
Ca
2+
+
13
H
2
O
3
C
9
H
19
OH
+
2
CaCr
2
O
7
+
16
H
+
⟶
3
C
8
H
17
COOH
+
4
Cr
3+
+
2
Ca
2+
+
11
H
2
O
3
C
10
H
21
OH
+
2
K
2
Cr
2
O
7
+
16
H
+
⟶
3
C
9
H
19
COOH
+
4
Cr
3+
+
4
K
+
+
11
H
2
O
3
C
9
H
19
OH
+
4
CaCrO
4
+
20
H
+
⟶
3
C
8
H
17
COOH
+
4
Cr
3+
+
4
Ca
2+
+
13
H
2
O
3
C
10
H
21
OH
+
2
CaCr
2
O
7
+
16
H
+
⟶
3
C
9
H
19
COOH
+
4
Cr
3+
+
2
Ca
2+
+
11
H
2
O
3
C
11
H
23
OH
+
2
K
2
Cr
2
O
7
+
16
H
+
⟶
3
C
10
H
21
COOH
+
4
Cr
3+
+
4
K
+
+
11
H
2
O
3
C
10
H
21
OH
+
4
CaCrO
4
+
20
H
+
⟶
3
C
9
H
19
COOH
+
4
Cr
3+
+
4
Ca
2+
+
13
H
2
O
3
C
11
H
23
OH
+
2
CaCr
2
O
7
+
16
H
+
⟶
3
C
10
H
21
COOH
+
4
Cr
3+
+
2
Ca
2+
+
11
H
2
O
3
C
12
H
25
OH
+
2
K
2
Cr
2
O
7
+
16
H
+
⟶
3
C
11
H
23
COOH
+
4
Cr
3+
+
4
K
+
+
11
H
2
O
3
C
11
H
23
OH
+
4
CaCrO
4
+
20
H
+
⟶
3
C
10
H
21
COOH
+
4
Cr
3+
+
4
Ca
2+
+
13
H
2
O
3
C
12
H
25
OH
+
2
CaCr
2
O
7
+
16
H
+
⟶
3
C
11
H
23
COOH
+
4
Cr
3+
+
2
Ca
2+
+
11
H
2
O
3
C
12
H
25
OH
+
4
CaCrO
4
+
20
H
+
⟶
3
C
11
H
23
COOH
+
4
Cr
3+
+
4
Ca
2+
+
13
H
2
O
3
CH
3
OH
+
2
(NH
4
)
2
Cr
2
O
7
+
16
H
+
⟶
3
HCOOH
+
4
Cr
3+
+
4
NH
4
+
+
11
H
2
O
3
CH
3
OH
+
4
(NH
4
)
2
CrO
4
+
20
H
+
⟶
3
HCOOH
+
4
Cr
3+
+
8
NH
4
+
+
13
H
2
O
3
C
2
H
5
OH
+
2
(NH
4
)
2
Cr
2
O
7
+
16
H
+
⟶
3
CH
3
COOH
+
4
Cr
3+
+
4
NH
4
+
+
11
H
2
O
3
C
2
H
5
OH
+
4
(NH
4
)
2
CrO
4
+
20
H
+
⟶
3
CH
3
COOH
+
4
Cr
3+
+
8
NH
4
+
+
13
H
2
O
<<
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