Synthesis of 3-[5-(4-substituted) phenyl-1,3,4-oxadiazole-2yl]-2-styrylquinazoline-4(3H)-ones was carried out by following steps: Step 1: Synthesis of 4- substituted benzaldehyde semicarbazon51(2) Semicarbazide Hydrochloride (0.1M) and sodium acetate (0.2M) was added and dissolved in 15-20ml of distilled water placed in flat-bottomed flask. In a separate beaker containing required aromatic aldehyde (1) (0.1M) was dissolved in aldehyde free alcohol. This ethanolic aromatic aldehyde solution was added slowly to the solution of semicarbazide hydrochloride. The precipitate, which gets separated, was filtered, dried and recrystallised from 95% hot ethanol. Table 1: Quantity of aldehydes taken S. No. Aldehydes Molecular weight Quantity taken …show more content…
CH3 175 83.06% 287-289ºC 4. -OCH3 191 86.03% 275-277ºC 5. 204 78.78% 295ºC Step-3 Synthesis of 2-Methyl benzoxazin -4(3H)-one53 (4) Anthranilic acid (0.1M, 18g) was taken in acetic anhydride and refluxed under anhydrous conditions for 4 hrs. Excess of acetic anhydride was then distilled off under reduced pressure. Obtained product was immediately used for next step. Step-4 Synthesis of 2-Methyl-3-[5-(4-substituted)phenyl-1,3,4- oxadiazole-2-yl]- quinazoline-4(3H)-ones53 (5) To the mixture of benzoxazinone (4), 2-Amino-5-aryl -1,3,4-oxadiazole (0.1M) in 100ml of glacial acetic acid was added and refluxed under anhydrous condition for 4 hrs. After cooling it was poured into crushed ice. The solid separated out was filtered thoroughly washed with cold distilled water, dried and recrystallised from hot ethanol (95 %). 5 Table 5 : Quantity of Oxadiazoles taken for synthesis S.No. Oxadiazoles Mol. Wt. Quantity taken in g 1 2-Amino-5-phenyl-1,3,4-oxadiazole 161 16.1 2 2-Amino-5-(4-chloro)phenyl-1,3,4-oxadiazole 195.5 19.55 3 2-Amino-5-(4-methyl)phenyl-1,3,4-oxadiazole 175 17.5 4 2-Amino-5-(4-methoxy)phenyl-1,3,4-oxadiazole 191 19.1 5 2-Amino-5-(4-dimethylamino)phenyl-1,3,4-oxadiazole 204
Abstract: In this experiment, triphenylmethanol was synthesized in two steps. First, the bromobenzene was reacted with dry magnesium turnings to produce Grignard reagent. Second, the Grignard reagent was reacted with methyl benzoate and concentrated sulfuric acid to produce an alcohol. The end result of the experiment was not very successful because only 17% yield of final product triphenylmethanol was recovered, and the final product was impure based on the melting point and the IR spectrum results.
One of the most important aspects of this experiment is to add the reagents in the specific order. First, the acetone and base solution is added and allowed time to react. This time lapse allows for the formation of carbanions. If all of the reagents were added at the same time, some carbanions would form, and some Cannizzaro products would form as well. Since benzaldehyde was not added until after the carbanion formation, the Cannizzaro reaction should not have happened.
In this lab, three unknown compounds were separated from a mixture and identified by melting point. Unknown mixture #124 has components of acid, base and neutral compound. The compounds were identified by melting point and matched up with the known melting points from a given list. In order to identify the compound it was important to separate by dissolving the mixture in an organic solvent which was not soluble in water, and then extracting the solution first with HCl, and then dilute sodium hydroxide solution. From the separation mixture, the aqueous layer were obtained and labeled as TT-1 (base), TT-2(acid) and TT-3 (neutral) in three different test tubes for later recovery.
The purpose of this experiment was to learn about the electrophilic aromatic substitution reactions that take place on benzene, and how the presence of substituents in the ring affect the orientation of the incoming electrophile. Using acetanilide, as the starting material, glacial acetic acid, sulfuric acid, and nitric acid were mixed and stirred to produce p-nitroacetanilide. In a 125 mL Erlenmeyer flask, 3.305 g of acetanilide were allowed to mix with 5.0 mL of glacial acetic acid. This mixture was warmed in a hot plate with constantly stirring at a lukewarm temperature so as to avoid excess heating. If this happens, the mixture boils and it would be necessary to start the experiment all over again.
There are several different reactions that can be used to synthesize an alkene product, however the main reaction being utilized for this experiment is the Wittig reaction and the Horner-Wadsworth-Emmons modification. The Wittig reaction involves a reaction between an aldehyde or ketone and ylid, which is also referred to as the Wittig reagent. The Wittig reagent is synthesized from a phosphonium salt and a strong base (Wittig Reaction, 2006). The reaction between the Wittig reagent and the ketone or aldehyde is a nucleophilic substitution; the carbon double bonded to the oxygen in the carbonyl is replaced with a carbon double bonded to another carbon (University of Liverpool, 2008).
Wt. Mass Density Appearance 2-methycyclohexanol 0.75 mL 114.19 g/mol 0.93 g/mL Clear colorless liquid 85% Phosphoric acid 1.00 mL Clear
Benzyne Formation and the Diels-Alder Reaction Preparation of 1,2,3,4 Tetraphenylnaphthalene Aubree Edwards Purpose: 1,2,3,4-tetraphenylnaphthalene is prepared by first producing benzyne via the unstable diazonium salt. Then tetraphenylcyclopentadienone and benzyne undergo a diels-alder reaction to create 1,2,3,4-tetraphenylnaphthalene. Reactions: Procedure: The reaction mixture was created. Tetraphenylcyclopentadienone (0.1197g, 0.3113 mmol) a black solid powder, anthranilic acid ( 0.0482g, 0.3516 mmol) a yellowish sand, and 1,2-dimethoxyethane (1.2 ml) was added to a 5-ml conical vial.
Lecturer Date Introduction Theoretical Background Procedure The procedure was segmented into two categories, the reaction set up and the crude product isolation. Reaction set up The magnetic stirrer was prepared through placing it in the fume cupboard. 1 mmol of L-Phenylalanine was placed and weighed in a 5 mL conical vial.
The reaction to synthesize benzocaine was known as a Fisher esterification reaction. The Fisher esterification was reaction between alcohol and carboxylic acid in the presence of acid. The reaction was used to form an ester. In the experiment, sulfuric acid acted as a catalyst and necessary for this reaction to occur. There was a change between the –OH group of carboxylic acid to an –OCH2CH3 group in the reaction.
The purpose of this experiment was to identify the two components of an unknown mixture through diverse experimental techniques such as recrystallization, extraction, melting point, and acid-base reactions. From this, the group to which these two compounds belong to had to be determined. These groups are: Carboxylic Acids, phenols, and neutrals. By determining the melting points of the two unknown compounds, these values were compared to the values of melting points in the chart and the proper compound was selected. For the case of this experiment, the unknown mixture contained, 4-methylbenzoic acid.
The purpose of this experiment was to learn about metal hydride reduction reactions. Therefore, the sodium borohydride reduction of the ketone, 9-fluorenone was performed to yield the secondary alcohol, 9-fluorenol. Reduction of an organic molecule usually corresponds to decreasing its oxygen content or increasing its hydrogen content. In order to achieve such a chemical change, sodium borohydride (NaBH4) is used as a reducing agent. There are other metal hydrides used in the reduction of carbonyl groups such as lithium aluminum hydride (LiAlH4).
This product undergoes base catalysed hydration giving dibenzalacetone. Sodium hydroxide is a catalyst in the reaction because the NaOH reacts with water. Following this is then the
Next, the oxygen is protonated from the 3-nitrobenzaldehyde, which is then followed by an elimination reaction where this acts as a leaving group. The product is the trans-alkene present in the product. After the reaction was completed, purification of the product was conducted using semi-microscale recrystallization.
To analyze the acetanilide product of the reaction, 1H NMR and IR were used. Results, Discussions, and Conclusions In this experiment, acetanilide was synthesized via nucleophilic acyl substitution from both acetic anhydride and aniline. During this reaction, aniline acts as the nucleophile and acyl (CH3CO-) group from acetic anhydride acts as the electrophile.
If impure, preform recrystallization procedure to remove the impurities. Then calculate Percent Recovered on crystals formed, and preform melting point procedure. 2. You find that a solid substance you are trying to purify is very soluble in ethanol, but not very soluble in water. You decide that you are going to try to recrystallize it from a solvent pair, consisting of ethanol and water.