Ethyl vinyl ether was used to protect –OH on glycidol based on a literature reported protocal.59 In a typical procedure, 0.675 mol glycidol and 200 mL ethyl vinyl ether were loaded in a round-bottom flask, to which 1.25 g TsOH was then added. The reaction was allowed to proceed at room temperature (RT) for 3h. The resulting mixture was then purified by washing with 100 ml saturated aqueous solution of NaHCO3 for 3 times. The organic layer obtained was dried by MgSO4. After filtration of MgSO4, the excess ethyl vinyl ether was removed by rotary evaporation.…
In Experiment 12B we used an umpolung reagent in an umpolung synthesis to synthesize benzoin from benzaldehyde. Umpolung synthesis is a synthetic approach that allows us to switch the identity of a reacting species. For example, the normal chemical reactivity of a nucleophile can be switched to one of an electrophilic compound. Two common agents are cyanide and thiamine (Vitamin B). The mechanisms for both agents are the same.…
To begin the first part of the experiment, zeolite and magnetized zeolite had to be synthesized. First, it was necessary to set up a contraption to hold a thermometer in place. This was done using a split cork and a 3 prong clam on a ring stand. 50 mL of 3.0 M NaOH was then added to a 250 mL beaker with a magnetic stir bar placed inside. After placing the solution on the stir bar, 3.7560 g of (sodium aluminate) was added to the solution.…
CAUTION: It is best not to get dichloromethane on your skin. Gloves are to be worn during this experiment, if improper safety precautions are taken there is a possibility of irritation, and or burning of the skin. CAUTION: Gas will build up in the separatory funnel while you are shaking it, so you must vent the funnel occasionally to prevent the stopper from popping out, causing a mess and possibly getting dichloromethane on your skin.…
Green Chemistry and the Diels-Alder Reaction Purpose The purpose of this reaction is to bring about the movement of green chemistry which is a safer, more sustainable chemistry to all levels of chemistry. The use of 12 principles can make in principle a reaction greener with the use of modifications. In this lab, the Diels-Alder reaction will be performed by reacting (E,E)-2,4-hexadien-1-ol with maleic anhydride without the use of a solvent to make the reaction more greener.…
The reaction mechanisms for bromination and nitration of toluene are indicated in Figure 1 and Figure 2. The meta-bromotoluene and meta-nitrotoluene did not really form compared to the para-bromotoluene and para-nitrotoluene, which yielded the most product, because it did not form the most stable resonance structure with the carbocation at the methyl attachment like para-bromotoluene and para-nitrotoluene. On the other hand, ortho-bromotoluene and ortho-nitrotoluene has the same mechanism as para-nitrotoluene. The bromination of toluene resulted in a yield of 0.790 g (4.62 mmol, 46.2%) major products and para-bromotoluene and ortho-bromotoluene, while the nitration of toluene had a yield of 0.646 g (4.71 mmol, 51.3%) para-bromotoluene and…
In this experiment, the reactivities of various halogenoalkane, 1-bromobutane, 2-bromobutane, 1-chlorobutane, 2-bromo-2-methylpropane, and 1-bromo-2-methylpropane were tested using two different solutions, NaI in acetone and AgNo3 in ethanol. The rate of reaction, the carbocation stability of each substrate, and the identity of the leaving group could be used to determine the mechanism of a reaction. With NaI in acetone, primary halides, such as 1-bromobutane and 1-chlorobutane were the most reactive substrates, when bromine or chlorine is ionized. Also, the influence of a strong nucleophile (I-) and the steric hindrance as the main barrier to prevent or retard the reaction, make this reaction a second order-Sn2 mechanism. With AgNO3 in ethanol,…
When conducting the procedure portion of the experiment, after measuring the mixture of cyclohexane and toluene for the simple distillation, it was observed that it took three scoops anhydrous sodium sulfate to dry the sample. It was observed that eh liquid started to boil at 25 degrees Celsius. The first drop of distillate was collected at 77 degrees Celsius. It was observed that the temperature gradually increased. The last drop of the distillate was collected at a temperature of 106 degrees Celsius.…
A Molecular Explanation of How the Fog Is Produced When Dry Ice Is Placed in Water The primary purpose of the article is to correct a common misconception about the origin of the fog, in the Dry Ice in Water Fog (DIWF), and to give further insight into happenings on a molecular level in the (DIWF) with the aid of experimental evidence. The writer is keen on proving that the fog produced in the (DIWF) demonstration is actually from the bulk water onto which the dry ice is placed and not the atmospheric water vapor. In a bid to understand the mechanism of the formation of fog, the writer employs a model, where the interaction of dry ice with other liquids is closely observed, and the effectiveness of experimental conditions in producing fog…
Fractional distillation is a common method for separating components of a mixture by utilizing their boiling points to aid in the separation. As a mixture is heated, the component with the lower boiling point in the mixture vaporize, while the higher boiling point component will remain in solution. These vapors will rise to a cooler area where they will condense and this liquid will then be collected; this is known as the distillate. Eventually, the lower boiling component will boil off, and the higher boiling point component will begin to travel up into the condenser as the temperature reaches the boiling point of the second component. As the second distillate is collected, it will mostly contain the higher-boiling component.…
Experiment 5 Synthesis and NMR Spectroscopy of ethyl cinnamate Introduction: Wittig reactions involve the stereoselective synthesis of olefins from phosphonium ylides and aldehydes or ketones, where the carbonyl bond is converted to an alkene double bond.1 The variety of suitable reagents and the relatively mild experimental conditions facilitate their industrial applications, such as the synthesis of epoxides, esters, carotenoids and vitamin A.2,3 Specifically, the ester ethyl cinnamate is used as a flavouring agent and in perfumes. The diastereomers of the alkene are distinguished through Proton Nuclear Magnetic Resonance (1H NMR) spectroscopy, where the coupling constants of alkenyl protons are different for (E) and (Z) isomers.4…
In this lab, we carried out a variety of reactions using different chemicals and metals. A chemical reaction is when the chemical state of the substance you are testing rearranges its ionic and molecular structure. One of the reactions we experienced was single replacement, this consists of one ion switching places with another ion to form a new compound. Another reaction we saw was double replacement. In this reaction, two compounds ions are switched to form two new compounds.…
After starting with 30 mL of an unknown mixture of two solvents, fractional distillation and gas chromatography were used to identify the unknowns as acetone and toluene in a 1 to 2.04 ratio of acetone to toluene. Fractional distillation was first used to separate the unknown mixture into its components based on boiling point. Distillation refers to the method of separating components of a mixture through heating and cooling. Simple distillation, which is especially useful in the separation of less-volatile substances from volatile substances, such as sugar from water, can be used to separate a liquid-liquid mixture if the boiling points of the component liquids differ by more than 40-50°C. A plot of temperature versus volume for a simple…
One important aspect of organic chemistry is the synthesis of new compounds. It is also important for chemists to understand how to perform certain techniques, such as extraction and distillation, to produce the new products, which are usually drugs and cures for illnesses. In this experiment, n-butyl bromide was produced. n-Butyl bromide is an alkyl halide, which are usually synthesized by an alcohol and an acid. In the case of n-butyl bromide, n-butyl alcohol was used along with sodium bromide and sulfuric acid.…
The result was a 66% yield of benzocaine which is significantly higher than the typical yield of the synthesis of benzocaine from p-toluidine as performed in this experiment. Ding and Chang-Ze describe the synthesis of benzocaine from p-nitrotoluene using KMnO4 as the oxidizing agent, which is the same as used in this experiment, SnCl4 as the catalyst, which differs from this experiment, and H2 as the reducer, which is the same as used in this experiment. This method resulted in a 70.3% yield under optimal…