Mapua Institute of Technology
Organic Chemistry Laboratory 2 Final Report
Factors Affecting the Relative Rates of Electrophilic Aromatic
Substitution Reaction
Justiniano, Priscilla Raiza N.
School of Chemical Engineering and Chemistry, Mapua Institute of Technology, Intramuros, Manila, Philippines
Experiment No.1, Submitted on August 6, 2011 at N402.
Abstract
EXPERIMENT NUMBER ONE IS ALL ABOUT THE ELECTROPHILIC SUBSTITUTION OF AROMATIC COMPOUNDS. AROMATIC COMPOUNDS ARE THOSE ORGANIC COMPOUNDS WHICH HAVE BENZENE RING (CYCLOHEXA-1,3,5-TRIENE). AROMATIC COMPOUNDS ARE ALWAYS FOLLOWS THE SUBSTITUTION REACTION BECAUSE OF THE STABILITY OF THE BENZENE RING. IT WILL NOT PROCESS THE ELIMINATION, ADDITION OR REARRANGEMENT REACTION.
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b. Chlorobenzene- is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.
c. Aspirin- is a salicylate drug, often used as an analgesic to relieve minor aches and pains, as an antipyretic to reduce fever, and as an anti-inflammatory medication.
d. Acetanilide- is an odorless solid chemical of leaf or flake-like appearance. It is also known as N-phenylacetamide, acetanil, or acetanilide, and was formerly known by the trade name Antifebrin.
e. p-Nitrophenol- is a phenolic compound that has a nitro group at the opposite position of hydroxy group on the benzene ring.
f. Anisole- is the organic compound with the formula CH3OC6H5. It is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances. The compound is mainly made synthetically and is a precursor to other synthetic compounds.
g. Phenol- is an organic compound with the chemical formula C6H5OH. It is a white, crystalline solid. This functional group consists of a phenyl, bonded to a hydroxyl (-OH).
The Apparatus/ materials used are the following: a. Test tube rack - is used in a laboratory and it is used to hold/support test tubes containing chemicals waiting for further operations.
b. Hot water bath- is when you
3. The IR spectrum of the starting material shows a medium/strong C-O bond at around 1500cm-1, also the starting material shows a strong C-H bond at around 3000cm-1 and another medium C-H bond at 2865cm-1 indicating an aldehyde group whereas the product does not. The IR spectrum of the product shows a two weak broad O-H peaks at around
I identified my unknown component as acetanilide based on the melting point ranges recorded during melting point analysis. The most important thing to remember is that acetanilide possibly replaced Tylenol as a component in Panacetin. It is necessary to continue to work to uncover the true components of Panacetin because it has remained to be a common pain relief medication in the drug
group. The location of this hydroxyl functional group will impact the molecular structure of the
The structure and molecular weight and formula for benzoic acid are as seen in Figure 1. This chemical is used as a preservative, and is deemed safe for consumption under specific levels.5
2. Using the atom and bond library below, construct the following molecule. It may be
This was concluded by combining information on melting points and TLC; melting range narrowed when filtered product was mixed with the standard product. Also, the Rf value of the pure product is closely related to the Rf value of the standard. TLC of filtrate showed no movement of the substance in the mixture under 9:1 ratio declaring the substance to be extremely polar. Of the three potential unknown reactants, 4-methoxyphenol would be the most polar and therefore would travel least up the TLC plate. (Q14:Yield) 81.2% product yield was collected. “Matter cannot be created nor destroyed”, therefore some product could have filtered through. TLC of filtrate confirmed remnants of product present. Filtering the filtrate could have increased the yield. (Q15:Recovery) The percent recovery of the product makes sense because it is the mass of the crystallized product divided by the crude product: 94.9%. The percentage reflects the mass of pure product (without the presence of impurities). (Q16:MP) Melting point coincides with the unknown nucleophile being 4-methoxyphenol because when the standard product was combined with our pure product, the melting range narrowed. When compared to the melting ranges obtained when mixed with the other two possible products the melting ranges significantly decreased and widened. This is often an indication of impurities being present, but because this was a
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.
Aspirin also known as acetylsalicylic acid is a salicylate drug, often used as an analgesic to relieve minor aches and pains, as an antipyretic to reduce fever, and as an
The purpose of Experiment 6 - Part 1, was to use electrophile addition to synthesize 1,2‐dibromo‐1,2‐diphenylethane from (E)-1,2-diphenylethene. The final product was correctly identified by the use of TLC and melting point determination. The final product was meso-1,2‐dibromo‐1,2‐diphenylethane. Figure 1. Reaction for Experiment 6, Part 1. Created by Chem Doodle.
(compound complex)In the articles "Like Black Smoke" by Diana Childress and "A World Turned Upside
In the experiment, Luminol Synthesis and Chemiluminescence, the purpose is to create luminol using the base-mediated reduction of 5-nitro-2,3,-dihydrophthalazine-1,4-dione and to investigate the chemiluminescence reaction that luminol is known for. 5-nitro-2,3-dihydrophthalazine-1,4-dione was reduced using sodium hydrosulfite in a solution of sodium hydroxide under reflux conditions. Acetic acid was used to precipitate the solid luminol product, later the product was collected through vacuum filtration. The luminol product emitted a blue light when a dilute solution of it and sodium hydroxide was mixed with a dilute hydrogen peroxide and potassium ferricyanide solution. The blue light seen correlates to the excited molecules that are dropping
Aromatic compounds can undergo electrophilic substitution reactions. In these reactions, the aromatic ring acts as a nucleophile (an electron pair donor) and reacts with an electrophilic reagent (an electron pair acceptor) resulting in the replacement of a hydrogen on the aromatic ring with the electrophile. Due to the fact that the conjugated 6π-electron system of the aromatic ring is so stable, the carbocation intermediate loses a proton to sustain the aromatic ring rather than reacting with a nucleophile. Ring substituents strongly influence the rate and position of electrophilic attack. Electron-donating groups on the benzene ring speed up the substitution process by stabilizing the carbocation intermediate. Electron-withdrawing groups, however, slow down the aromatic substitution because formation of the carbocation intermediate is more difficult. The electron-withdrawing group withdraws electron density from a species that is already positively charged making it very electron deficient. Therefore, electron-donating groups are considered to be “activating” and electron-withdrawing groups are “deactivating”. Activating substituents direct incoming groups to either the “ortho” or “para” positions. Deactivating substituents, with the exception of the halogens, direct incoming groups to the “meta” position. The experiment described above was an example of a specific electrophilic aromatic
Acetaminophen also known as paracetamol and APAP, is a prescription and over-the-counter drug that is used to treat moderate pain and reduce fever. It is also paired with other ingredients. For example, acetaminophen is mixed with guaifenesin and phenylephrine to make the allergy medication Mucinex, acetaminophen is also used in over 600 other medications. When mixed with an opioid, such as, tramadol, it can be used to treat more severe pain. It is usually taken through the mouth but it can also be taken through injection and as a
Amphoteric – used in cleansing products which include ingredients such as cocamidopropyl betaine, cocoamphopionate, and sodium lauraminopropionate. Less irritating and can make formula thicker which is idea for creams. Mild and gentle on the skin
Isopentyl acetate, banana oil, is a naturally occurring compound that has a very distinct and recognizable odor. It is most commonly found in bananas but also can be found in other organisms.