My refractometer reading was 1. I obtained a yield of 0. Because of their high electron density, acylation of ferrocene is accomplished under milder conditions using a phosphoric acid as acid catalyst. The second step is the abstraction of a proton from the carbocation on the ring by some base characterized as the fast step. A formal lab report must be typewritten and will be graded according to how well it is written as well as on the content. After addition of the above reagents was complete, 1. After the first crystals appeared in the boiling mixture, the flask was allowed to cool to room temperature, and then placed in an ice bath to complete the crystallization.
These experiments examine the behavior of the aromatic ring, when exposed to electrophilic reagents, and the preferred orientation of the resultant product based on which attached substituent groups are already present. The experiment yielded an oily, clear substance weighing 0. The ob served melting point of the product was 96 - 98°C, which is considerably lower than the literature value of 104 — 105°C. It can be applied to both liquid and solid samples, and multi-component mixtures. The known refractive index value is about 1. The reaction product is isolated and purified by microscale flash column chromatography.
A mobile phase solvent, or eluent, is used to desorb solute molecules, carrying them along the column to a receiving flask. The charcoal was removed by gravity filtration. The acylation produced para- Methoxyacetophenone. The percent yield of the product was 57. Mentioning techniques learned is acceptable. There is no exception to turning in a completed laboratory notebook for each experiment, regardless whether a formal written lab report is turned in. You should list quantities of important reagents, but only if they are essential to understand how the experiment was performed.
The reaction was then allowed to go to c ompletion at room temperature, and the crystals were washed with water and methanol. You do not include every detail of the experiment, because certain techniques, such as Separatory Funnel extractions, melt point determinations, and refluxing because these techniques are known to everyone do not include items like boiling stones, etc. Namely, these reactions are succeptible to rearrangements and polysubstitution. There are only a few formal reports turned in during the semester, and the experiments that can be used for a formal written report are listed in the syllabus. Introduction to Organic Laboratory Techniques, 3rd ed.
When a formal written lab report is required, the format changes for this report, as it is not just the content of the laboratory notebook. Chromatography takes advantage of the differences in polarity and binding strength that the components of a mixture have for column adsorbents. These activating groups direct ortho and para. A product yield and percent yield calculations were performed on the dry material. A suspension of p-nitroacetanilide isomers resulted. At first, I wondered why I couldn't directly nitrate aniline to make p-nitroaniline it is strongly activating, the para product would seem likely.
Overall, these reactions demonstrate one of the most practical organic chemistry synthesis techniques. The upper organic layer was collected and saved. The acylium cation is produced from acetic anhydride, which also serves as a solvent for this reaction. Do not use outlines, although tables can be used for reagents if there are more than a few reagents. Equilibrium is established between binding to the stationary phase and solubility in the mobile phase.
The sample was then air dried. After 20 minutes, including the time required for adding the nitric acid-sulfuric acid mixture, 25 mL of ice water were added. If both rings react, then the product is the red 1,1-diacetylferrocene. This particular experiment initially brought about some confusion. . This was lower due to the fact that many of the crystals were stuck in the reaction tube and could not be removed for weighing. Solid product crystals were isolated using vacuum filtration with a Büchner funnel.
Sensors and Equipment This experiment features the following Vernier sensors and equipment. It is important to turn in your formal written lab reports in order to get the maximum number of points possible. Lab 6: Electrophilic Aromatic Substitution 1 Nitration of Methyl Benzoate 2 Synthesis of 1,4-Di-t-butyl-2,5-dimethoxybenzene byFriedel-Crafts Alkylation of 1,4-DimethoxybenzenePurpose1 To carry out the nitration of methyl benzoate, and then identify the major product formed position at which. After the 15-min incubation, the reaction was stopped by pouring the room temperature reaction mixture over 50 g of crushed ice. Materials and Methods Describe your experimental protocol and the materials reagents used.
As the solvent polarity increases, more tightly bound polar molecules, firmly held by the adsorbent, establish equilibrium with the eluting solvent and flow along the column. Second, the newly added nitro group, when attached to the ring, would lead to additional deactivate. If you do better than expected of a good report, you will have points added to give a higher score. Substituents on a ring can either be activating or deactivating. Your lab report should follow the pattern described below. Toluene was used as substrate using the acylating agent acetyl chloride. It must be noted that the attack generates a carbocation not because of a positive charge on the electrophile, but because a pair of electrons are pulled out of the ring to form a bond with the electrophile leaving a carbon in the ring electron deficient.
If your formal report is turned in after that two week late period, you will lose an additional 3 points or a total of 9 points 30% deduction. Results and Discussion Describe your results, including pertinent experimental techniques that are specific for your experiment. Acylation requires an electron rich aromatic ring system and cannot contain any electron withdrawing substituents on the ring. In this experiment you will also become familiar with a technique called column chromatography, which can be used to separate the desired product from unreacted starting material and side products. Formal written reports will be worth a maximum of 30 points.