Nitration of aromatic groups
Description: Aromatic groups can be nitrated by the action of nitric acid and an acid catalyst
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Org. Synth. 1923, 3, 71
DOI Link: 10.15227/orgsyn.003.0071
Org. Synth. 1930, 10, 74
DOI Link: 10.15227/orgsyn.010.0074
Org. Synth. 1934, 14, 68
DOI Link: 10.15227/orgsyn.014.0068
Org. Synth. 1942, 22, 48
DOI Link: 10.15227/orgsyn.022.0048
Org. Synth. 1949, 29, 72
DOI Link: 10.15227/orgsyn.029.0072
Org. Synth. 1941, 21, 96
DOI Link: 10.15227/orgsyn.021.0096
Org. Synth. 1947, 27, 62
DOI Link: 10.15227/orgsyn.027.0062
Org. Synth. 1945, 25, 78
DOI Link: 10.15227/orgsyn.025.0078
Org. Synth. 1955, 35, 3
DOI Link: 10.15227/orgsyn.035.0003
Org. Synth. 1950, 30, 22
DOI Link: 10.15227/orgsyn.030.0022
6 thoughts on “Nitration of aromatic groups”
Hessung, the reason is because it is a Lewis acid base reaction between the sulfuric acid and the nitrate ion. This is a necessary step in preparing the two groups for the SeaR reaction to follow.
For step 1, the half arrow leading to OH2 should be a full arrow?
It’s meant to be a full arrow, new diagrams will be up soon that make it much more clear.
In the mechanism , on step one, why the oxygen which has negative charge attack hydrogen first?
why are there two lone pairs on the top oxygen in the middle figure between step one and two of the mechanism? wasn’t one of the pairs used to grab the additional hydrogen?
Oops. Typo – thanks for pointing it out!