Analytical Differentiation Of 1 Alkyl 3

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

The purpose of this experiment was to synthesize the Grignard reagent, phenyl magnesium bromide, and then use the manufactured Grignard reagent to synthesize the alcohol, triphenylmethanol, by reacting with benzophenone and protonation by H3O+. The triphenylmethanol was purified by recrystallization. The melting point, Infrared Spectroscopy, 13C NMR, and 1H NMR were used to characterize and confirm the recrystallized substance was triphenylmethanol.

Results and Discussion Synthesis of Compound 3. Scheme 1: Synthesis of Compound 3. To synthesize compound 3, an approach involving treating triptolide with dimethyl sulfide and benzoyl peroxide in acetonitirile was used (Scheme 1). This approach resulted in the formation of compound 4 with a 51% yield and in triptonide (5) with a 46% yield.

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

Through the use of the Grignard reaction, a carbon-carbon bond was formed, thereby resulting in the formation of triphenylmethanol from phenyl magnesium bromide and benzophenone. A recrystallization was performed to purify the Grignard product by dissolving the product in methanol. From here, a melting point range of 147.0 °C to 150.8 °C was obtained. The purified product yielded an IR spectrum with major peaks of 3471.82 cm-1, 3060.90 cm-1, 1597.38 cm-1, and 1489.64 cm-1, which helped to testify whether the identity of the product matched the expected triphenylmethanol. The identity of the product being correct was further confirmed by way of both proton and carbon-13 NMR spectra. This is due to the fact

Olmsted, John III; Williams, Greg; Burk, Robert C. Chemistry, 1st Canadian ed.; John Wiley and Sons Ltd: Mississauga, Canada, 2010, pp 399 - 406

In the primary ligand structure two methyls were stayed in meta state and the hydrogen of phenol was omitted.

This experiment explored the synthesis of triphenylmethanol through the use of Grignard reagents. The percent yield of the product was 10% on a relatively humid day. The melting point was calculate to be 127.2oC with a literature value of 162oC. An IR spectrum of the product was taken and used for positive identification of the product. The mechanism of the formation of triphenylmethanol was explored. Byproducts were also considered and their mechanisms duly noted.

Since the basic unshared electron pair is not part of the aromatic sextet, as in pyrrole, pyridinium species produced by N-substitution retain the aromaticity of pyridine. As shown below, N-alkylation and N-acylation products may be prepared as stable crystalline solids in the absence of water or other reactive nucleophiles. The N-acyl salts may serve as acyl transfer agents for the preparation of esters and amides. Because of the stability of the pyridinium cation, it has been used as a moderating component in complexes with a number of reactive inorganic compounds. Several examples of these stable and easily handled reagents are shown at the bottom of the

Benzothiazoles are heterocyclic compounds with multiple application and although they have been known from long ago to be biologically active.1-3 Recently, Racane et al4 have described the synthesis of bis-subsituted amidinobenzothiazoles as potential anti-HIV agents.

The functional group added during a Friedel-Crafts acylation reaction, deactivates the ring, resulting in a mono-substituted ring rather that a poly-substituted ring, which is produced from a Friedel-Crafts alkylation reaction.4 The mono-substituted product is then further reduced to get an alkyl substituted ring instead of yielding a product containing a ketone. To obtain the ketone product, an acyl group is added to an aromatic ring. However, for this reaction to take place, no electron withdrawing groups can be present on the aromatic ring, and an acyl halide must be used to obtain the acyl cation.5 These limitations are met, in the Friedel-Crafts acylation reaction of anisole with acetyl

The results are summarized in Table 2. Pleasingly, the results indicated that a range of arylmethyl chlorides with electron-neutral (H), electron-donating (Me and OMe) regardless of their position(s) on the aryl ring, afforded the desired products 2a–i in good to excellent yields. Unfortunately, benzyl chlorides including electron-deficient such as p-chloro and p- nitro groups did not participate in the cross-coupling reaction and desired products 2j and 2k were not detected in the reaction mixtures. Notably, 1,2-bis(chloromethyl)benzene reacted under the optimal conditions, and the corresponding product 3l was obtained in 79% yield. Furthermore, the fused-ring methyl chlorides 1m-o and heteroaromatic methyl chlorides 1p and 1q applied well under this conditions and gave corresponding anhydrides 2m–r in 75-86% yields. The (3-chloroprop-1-en-1-yl)benzene 1x was also smoothly converted to the corresponding carboxylic anhydrides 2x in good

The fragment ions at m/z 214, 186 and 144 have been observed in a number of 1-pentyl-3-acylindoles .These fragment ions do not contain the substituted dimethoxybenzoyl ring portion of these compounds. The ions at m/z 214 and m/z 186 represent cleavage of either of the bonds to the carbonyl carbon with the charge remaining on the indole portion of the molecule. The m/z 214 ion represents the loss of the substituted dimethoxybenzene radical and the m/z 186 represents the loss of the substituted dimethoxybenzoyl radical. The m/z 144 ion is the product of a hydrogen rearrangement from the m/z 214 cation with the elimination of the entire nitrogen substituted alkyl side chain [C5H10], unsubstituted benzoyl indole (1-n-pentyl-3-benzoylindole).

Both DEPT-45 and C13-NMR spectra, were combined, and we determined seven Carbon peaks that are associated with Ibuprofen, but there are some Carbon peaks that are not present on the spectra. These include the remaining two Carbons on the benzene ring and the Carbon that is in the carboxylic acid functional group. The theoretical peak locations for these Carbons would be 145-135 ppm for the aromatic Carbons and 200-180 ppm for the carbonyl Carbon. Our 60 MHz is not precise enough to separate these small peaks from the noise generated by the machine. Now with the specific number of Carbon-Hydrogen environments, we shall construct Ibuprofen’s structure via proton NMR techniques.

Attkins, R. C., & Carey, F. A. Organic Chemistry: A Brief Course; Mc Grawhill Inc.: New York, USA, 1990; p 205.