对硝基甲苯合成对氨基苯甲酸实验报告
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武汉大学化学与分子科学学院
有机化学实验报告
实验名称：synthesis of 4-aminobenzoic acid from 4-nitrotoluene
班级：化学弘毅班姓名：指导老师：熊英
实验日期： 5.11-6.8 星期：四实验室：化东514
二．反应原理：
三．主要试剂及产物的物理常数：
四．主要试剂用量及规格：
五．实验装置图：
六．时间表
七．实验步骤及现象：
The oxidation procedure:
The weight of crude p-nitrobenzoic acid: 0.85g
The weight of purified p-nitrobenzoic acid: 0.73g
TLC analyses:
Product(crude) p-nitrotoluene Product(purfied) p-nitrotoluene R f=0.18 R f=0.87 R f=0.17 R f=0.89 m.p. determination (crude product)
T first T totΔT T T average
1 234 239 5 236 237
2 235 239 4 237
m.p. determination (refined product)
T first T totΔT T T average
1 237 240 3 238 239
2 237 241 4 239
The reduction procedure:
The weight of crude p-aminobenzoic acid: 0.9020g
The weight of recrystallized p-aminobenzoic acid: 0.1103g
九．产率计算：
IR spectrum of p-nitrobenzoic acid
IR spectrum of p-aminobenzoic acid
Analysis of IR spectrum of the purified intermediate product (because the sample might have been a little thick, some peaks are not showed in the picture):
The little peaks around 2500~3000cm-1 indicate stretching vibration of O-H
The peak of 1690.03cm-1 indicates stretching vibration of C=O
The several peaks including 1617.32cm-1 and others on the right indicate stretching vibration of C=C in benzene ring
The peaks between 716~878cm-1 indicate out-of-plane vibration of C-H in benzene ring
The analysis shows the product contains carboxyl group. It indicates that the oxidation is complete.
Analysis of IR spectrum of the final product:
The peaks between 3364~3460cm-1 indicate stretching vibration of N-H
The wide range of peaks between 2500~3000cm-1 indicate stretching vibration of O-H
The peak of 1663.77cm-1 indicates stretching vibration of C=O
The peaks of 1601.28cm-1, 1574.21cm-1, 1522.49cm-1 indicate stretching vibration of C=C in benzene ring
The peak of 1421.30cm-1 indicates bending vibration of C-H
The peak of 920.04cm-1 indicates bending vibration of O-H
The peaks between 698~842cm-1 indicate out-of-plane vibration of C-H in benzene ring
The analysis shows the product which contains amino group and carboxyl group is the target molecule--p-aminobenzoic acid.
H-NMR of the final product
十一．参考文献：