Abstract
This experiment is about the synthesis of 3-nitrobenzaldehyde through nitration. The nitration of benzaldehyde is an example of an electrophilic aromatic substitution reaction, in which a proton of an aromatic ring is replaced by a nitro group. Many aromatic substitution reactions are known to occur when an aromatic substrate is allowed to react with a suitable electrophilic reagent, and many other groups besides nitro may be introduced into the ring. Although the reaction produced a low yield at the end, the yield is calculated from the reaction and limiting reagent.
Keywords: electrophilic aromatic substitution, nitration, aldehyde, nitrating group
Introduction
Electrophilic substitution happens in many of the
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Stage 1 of the mechanism of nitration
As the NO2+ ion approached the delocalised electrons in the benzene, those electrons were strongly attracted toward the positive charge.
Two electrons from the delocalised system were used to form a new bond with the NO2+ ion. Because those two electrons aren't a part of the delocalised system any longer, the delocalisation was partly broken, and in the process the ring gained a positive charge.
Stage two
Figure 2. Stage 2 of the nitration mechanism
The second stage involved a hydrogensulphate ion, HSO4-, which was produced at the same time as the NO2+ ion. This removed a hydrogen from the ring to form sulphuric acid - the catalyst had therefore been regenerated. The electrons which originally joined the hydrogen to the ring were now used to re-establish the delocalised system.
Table 1. Observations from the experiment proper
Observations:
89 mL conc. H2SO4
Clear solution
+ 45 mL fuming HNO3
Clear solution
+ 10.2 mL benzaldehyde
Solution turns yellow if stirred continuously while adding benzaldehyde. But solution will produce red orange fumes and increase heat.
+ ice
White fluffy precipitate
After vacuum filtration
White gum-like precipitate
+ 125 mL diethyl ether
Precipitate dissolves and solution turns into pale yellow color
+ 125 mL 5% NaHCO3
Immiscible with solution. Golden yellow in color.
While the experiment was being executed,
Objective: The objective of this lab is to observe the synthesis of 1-bromobutane in an SN2 reaction, to see how a primary alky halide reacts with an alcohol.
Mayo, D. W.; Pike, R. M.; Forbes, D. C. Microscale Organic Laboratory with Multistep and Multiscale Syntheses, 5th ed.; John Wiley & Sons, Inc., 2011; pp 132-135.
Gilbert, John and Stephen F. Martin. Experiment Organic Chemistry: A Miniscale & Microscale Approach. Belmont, CA: Thomson Brooks/Cole, 2010. 537-547. Print.
8. ISBN: 0-558-05245-2 Virtual ChemLab: General Chemistry, Student Lab Manual/Workbook, V. 2.5, Third Edition, by Brian F. Woodfield and
Purpose: The purpose of this experiment is to observe a variety of chemical reactions and to identify patterns in the conversion of reactants into products.
2. Plan: Each student in a group of three will work to create a reaction with the Benzonitrile Oxide with, cis-stilbene, trans-stilbene, or styrene in an Erlenmyer flask. With this Reaction solution thin layer chromatography will be performed using each reaction solution. The different reactions will then be compared by running co-spot TLC’s. An NMR of the crude products from each reaction will be taken.
This experiment was designed by conducting a substitution reaction to construct a complex compound (2-methylphenoxyacetic acid) from two simple parts; also known as synthesis - converting simple molecules into more complex molecules. A purification technique known as crystallization was used to purify the product. Suction filtration was used to filter out the product. The experiment was completed over a three-day experimental period.
The purpose of this experiment is to examine the reactivities of various alkyl halides under both SN2 and SN1 reaction conditions. The alkyl halides will be examined based on the substrate types and solvent the reaction takes place in.
Dictionary of organic compounds, 6th edition, Chapman and Hall, London, Volume 3(& Volume 6), 1996 Maria Lindsay and Sean P. Hickey, Organic chemistry lab 2 manual, department of Chemistry University of New Orleans
Fifield, F. W. and Kealey, D. 1995. Principles and Practice of Analytical chemistry. (4th ed) Glasgow, Blackie Academic and professional.
The reaction took place in a conical vial and .2mL of each of the reactant samples were added to it along with some 95% ethanol. Two drops of NaOH were added shortly after and stirred at room temperature for fifteen minutes. The vial was cooled in and ice bath and crystallized. Vacuum filtration was performed to filter the crude product. The crude product was recrystallized using methanol and filtered again. We made one change to the procedure and instead of using .7mL of ethanol we
Timberlake, K. C. (01/2014). Chemistry: An Introduction to General, Organic, and Biological Chemistry, 12th Edition.
The theory behind Organic Chemistry, I found to be very difficult to conceptualise due to the fact that molecules are so small we don’t see them with the human eye. Therefore, it is impossible to how bonds are broken, new bonds are formed, their size or their configuration. Consequently, I found the computer practical class helpful in showing us the different molecule structures and how they work together, bend and attach to each other to form the larger functional groups. Furthermore, seeing how sigma and pie bonds structure of the molecule will determine how or if the molecule is able to bend and
In this synthesis, 2.0g of benzophenone was dissolved in 50ml isopropyl alcohol in 50ml Erlenmeyer flask. In this solution, one drop of glacial acetic acid was added. It was then filled with isopropyl alcohol up to the brim. After, the flask was stoppered using a well-rolled cork. It was ensured that very little air as possible was trapped inside the flask. It was tightly bind using a parafilm. The flask was inverted and exposed to sunlight outside the laboratory.
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