by sodium borohydride (NaBH4) to produce the cis and trans isomers of 4-tert-butylcyclohexanol. Since the starting material is a ketone, NaBH4 is strong enough to perform a reduction and lithium aluminum hydride is not needed. NaBH4 can attack the carbonyl group at an equatorial (cis) or axial (trans) position, making this reaction stereoselective. After the ketone is reduced by the metal-hydride, hydrochloric acid adds a proton to the negatively charged oxygen to make a hydroxyl group. The trans isomer
compound had been fully oxidized then there would be no such alcohol present. Also, because of my IR, I know that my compound was one of the other 2 compounds because of the strong sharp absorption at 1705 wavenumbers. This indicates the presence of a carbonyl. Also, my 2,4-DNP test was positive. Therefore I had to prove which of the two compounds my final product was. The first was the oxidation of the primary alcohol, forming an aldehyde and a secondary alcohol. This could not have been my product because
ring from their substitution of one group of atoms. In other words, they can transfer acyl group to an aromatic ring. Friedel-Crafts has an acyl group that is attached to the structure that has aromatic ring. Acylation is used to give ketones. Carbonyl group makes electron to move back or move away in Friedel-Crafts Acylation, so it has not produced multiple acylations. Moreover, Lewis acid and acid anhydride are usually used in Friedel-Crafts Acylation. For example, the Friedel-Crafts Acylation
Addition reactions are a common chemical transformation of a carbon-carbon double bound. Carbon-carbon double bonds contain one pi bond, which is held together weakly, and one sigma bond. The weak pi bond of the alkene, like 1-hexene, can be broken if a strong base is added. The electrophile, aka the base, attacks the nucleophile of the molecule. A covalent bond forms between the base and the carbon, which is an exothermic and favorable reaction. In this specific experiment, 1-hexene and HBr were
Purpose: The purpose of this experiment is to determine the absolute configuration of an unknown chiral secondary alcohol using the competing enantioselective conversion (CEC) method. This method uses both R- and S- enantiomers of a chiral acyl-transfer catalyst called homobenzotetramisole (HBTM), in separate parallel reactions, and thin layer chromatography to identify the stereochemistry of the secondary alcohol, whether it be an R- or S- enantiomer. Quantitative analysis was performed using a
Depending on which face of carbonyl the hydride attacks, the ketone could result in two different diastereomers of product. Since the two ketone faces are nonequivalent, there will be stereo selectivity in reduction which means that one diastereomer will be more prevalent than the other. There are three reduction conditions can be used to reduce the 4-tert-butylcyclohexanone : NaBH4, MPV , and L-selectride. For NaBH4, the hydride attach itself to the carbonyl oxygen to become the hydroxyl group
The aim of this experiment is to carry out a reaction that results in the synthesis of Methyl Benzoate by Fischer Esterification. Methyl Benzoate is an organic compound, it is an Ester with the chemical formula C6H5COOCH3 and it is formed by the condensation of methanol and benzoic acid. Methyl Benzoate is strongly reminiscent of the fruit of the feijoa tree, and it is used in the making of perfumes. (6) (2)An Ester is a functional group which is derived from carboxylic acids, they are sweet and
predicting the vibration frequencies by using Gauss View. Furthermore, students were also able to demonstrate their skills in reading IR spectrums. For the first part of the lab, Michelle and I created the molecule benzophenone and determined the carbonyl stretch, which was 1770.10cm-1, and the C-H stretch which was at 3174.41cm-1. After predicting the stretches, we obtained the actual compound and ran an IR spectrum in order to observe the frequencies. However, the compound had to be placed in a
Draw the structure of the organic product for the reaction between the following compound and the phosphorus ylide shown. Solution The phosphorus ylide will only react with the carbonyl group. Final product Comment: Think of the Wittig reaction as the reverse of oxidative cleavage of alkenes. Baeyer-Viliger Oxidation The Baeyer-Viliger oxidation is an organic reaction used to convert a ketone to an ester using a peroxyacid, with an “insertion” of one oxygen atom
The IR spectrum RM-02-CC2 was obtained. The spectrum consisted of a carbonyl peak, an aromatic carbon-carbon double bond peak, and a sp2 hybridized carbon and hydrogen bond peak at 1713, 1598, and 734. These functional groups are all present in 9-flourenone. The carbonyl group specifically was important because fluorenone was the only that contained a carbonyl group. The Identity was further confirmed by the melting point, 79-80˚C. This value is similar to the known
1. Name of experiment (1 pt): Aniline acetylation by means of the use of acetic anhydride and recrystallization of crude acetanilide for purification. 2. Purpose of experiment (2 pts): The purpose of the experiment was to acetylate aniline with the use of acetic anhydride and purify the crude acetanilide by recrystallization; in addition, determine the percent yield for acetanilide. 7. Interpret the obtained results (20 pts): The yield of the crude acetanilide was fair (98.45%). This was apparent
For this experiment, we reduced a ketone to a secondary alcohol. During the first week, everyone ran the reaction using 9-fluoreneone. The ketones for week 2 were derivatives of acetophenone, and my group elected to test the differences in reactivity between acetophenone, 4-methyl-acetophenone, and 4-bromo-acetophenone. We hypothesized that the differences in reactivity would be affected by the electronegativity of substituent. Therefore, we predicted that the 4-bromoacetophenone react the
three phenyl groups bonded to a negatively charge carbon atom. To form a ylide, a triphenylphosphine attacks a primary or secondary alkyl halide to form phosphonium salt which is deprotonated. To obtain the desired product in a Wittig reaction, the carbonyl compound is treated with a ylide which forms a four-member ring called oxaphosphetane. The second step is to make a more stable bond, to achieve this an elimination occurs to form Ph3P=O (triphenylphosphine oxide) and as a result, forms the alkene
Even though the percent yield was extremely low (19.106%) and the melting point was lower than expected (85-88 degrees C and not 92-94 degrees C), the IR spectrum proved that the final product does not have a carbonyl group, as it was reduced to the alcohol group. The nitro group remain on the IR spectrum, proving that it was not reduced to Aniline. The TLC plate also proves a reduction has occurred, as the product Rf value (0.2195) was lower than the starting
nitrogen and carbonyl so it’s hydrophilic.2. Hydroxyl: hydrophilic because of the presence of Oxygen that can H-bond with water.3.benzene ring: lipophilic because of non-polar hydrocarbon ring. 4. Methyl is lipophilic because of the nonpolar hydrocarbon group. Aspirin: 1. Carboxylic acid: Oxygen that’s polar which can H-bond with water. 2. Ester: lipophilic because it is non polar although it has oxygen. 3. Benzene: lipophilic because of non-polar hydrocarbon ring. Phenyl butazone 1. Carbonyl: hydrophilic
Paracetamol – Synthesis and Uses Discovered in 1877 by Harmon Northrop Morse at the John Hopkins University, Paracetamol was one of several aniline deriviatives that was found to have analgesic and antipyretic properties (Brodie 23). It was first synthesized by the reduction of p-nitrophenol with tin in glacial acetic acid; however was not used classified as a medication until ten year later (Bertolini 264). Initially, phenacetin, a closely related compound that exhibited similar physiological
Once the reagent is formed it is further synthesized and then reacted with aldehyde or ketone to form a secondary or tertiary alcohol respectively, through its carbonyl group. For this
degrees Celsius. It is insoluble in water, but soluble in benzene, ethyl acetate, and alcohol. The solubility of Spironolactone increases with increasing polarity of the solvent. The IR spectrum of spironolactone shows a conjugate carbonyl group and a lactone carbonyl present in the structure
activation energy than what is required to turn camphor into borneol. Though borneol is the more stable product, the energy requirements to form isoborneol are lower because the borohydride is adding to the less sterically hindered point on the carbonyl carbon. The product made is then mostly (85%) isoborneol. More borneol would be expected if more energy was available during the reaction. ... ... middle of paper ... ...his purity calculation doesn't account for the singnal at 2.10ppm corresponding
molality to be too low, moles of solute to be too low and the molar mass to be falsely high. After doing an IR spectrum for unknown 149, the only information that could be determined about the structure was that it contained a hydroxide group, a carbonyl and a C-C aromatic bond somewhere in the structure. There was a lot of trouble getting a readable IR spectrum from unknown 149 but after numerous pellets made, it was later found that the printed spectrum would suffice for comparison to trans-Cinnamic