Lab 6 - Synthesis of Aspirin

Refer to the following information to answer questions 1 to 9: As a biotechnologist working for a pharmaceutical company, you as tasked with preparing the cardiac antiarrhythmic agent Amelfolide from p-nitrobenzyl chloride and 2,6-dimethyl aniline (Figure 2.1). You are provided the starting materials and asked to prepare 7.50g of pure material. No other instructions are given to you. MW 2,6-dimethylaniline = 121.18 g/mol MW p-nitrobenzyl chloride = 185.56 g/mol MW Amelfoliode = 270.29 g/mol %3D NH2 CI O2N O2N When developing a synthetic scheme, the first thing to do is check the scientific literature to see if someone has done this reaction before you. Upon performing a literature search, you identify a publication where a group from Japan has performed the same reaction you are tasked with completing. The paper is in Japanese and you cannot read the details of the procedure, however, you can make out that the reaction is performed using DCM as the solvent and proceeds with a yield of…

4) Multistriatin, one of the pheremones of the elm bark beetle, is a volatile compound released by a virgin female beetle when she has found a good food source - an elm tree. Male beetles, which carry the Dutch elm disease fungus, are attracted by the pheromone; the tree becomes infected with the fungus and soon dies. Multistriatin is used to trap the beetles, but the amount in beetles is so miniscule that the compound must be synthesized. The following synthesis of multistriatin uses only chemistry that we have seen in Chem 348. HO. НО Br type O type. H type H H CH3 H HO HO type O H CH3 "Η OH type H hint: anhydrous cond CH3 H = H type type HO CH3 H H type CH 3 H Multistriatin Multistriatin

Estrogens are female sex hormones, the most potent of which is B-estradiol. OH AYA Но B-Estradiol In recent years, chemists have focused on designing and synthesizing molecules that bind to estrogen receptors. One target of this research has been nonsteroidal estrogen antagonists, compounds that interact with estrogen receptors and block the effects of both endogenous and exogenous estrogens. A feature common to one type of nonste- roidal estrogen antagonist is the presence of a 1,2-diphenylethylene with one of the benzene rings bearing a dialkylaminoethoxyl substituent. The first nonsteroidal estrogen antagonist of this type to achieve clinical importance was tamoxifen, now an important drug in the treatment of breast cancer. Tamoxifen has the Z configuration shown here. NMeg A B NMeg ? ОН Tamoxifen Propose reagents for the conversion of A to tamoxifen. Note: The final step in this synthesis gives a mixture of E and Z isomers.

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6. The reaction between aniline and nitrous acid at low temperature yields A) an N-nitroso amine B) a diazonium salt C) a nitrile D) an amine nitrite salt 7. An organic nitrogen compound, X, gives ammonia on warming with dilute aqueous sodium hydroxide, X could be A) ethanamide B) ethylamine C) phenylamine D) amino ethanoic acid

Eistrogens are female sex hormones, the most potent of which is B-estradiol. OH H,C но B-Estradiol In recent years, chemists have focused on designing and synthesizing molecules that bind to estrogen receptors. One target of this research has been nonsteroidal estrogen antagonists, compounds that interact with estrogen receptors and block the effects of both endogenous and exogenous estrogens. A feature common to one type of nonste- roidal estrogen antagonist is the presence of a 1,2-diphenylethylene with one of the benzene rings bearing a dialkylaminoethoxyl substituent. The first nonsteroidal estrogen antagonist of this type to achieve clinical importance was tamoxifen, now an important drug in the treatment of breast cancer. Tamoxifen has the Z configuration shown here. но NMe, NMeg ? B NMeg ? "NMe, ОН Tamoxifen Propose reagents for the conversion of A to tamoxifen. Note: The final step in this synthesis gives a mixture of E and Z isomers.

Why is methyl salicylate so easily absorbed through the skin?

Find the structural formulas for salicylic acid, acetic anhydride, and aspirin. Use these structural formulas to construct a reaction equation describing the synthesis of aspirin.  (CH3CO)2O + HOC6H4COOH → CH3CO2C6H4CO2H + CH3COOH acetic anhydride   salicylic acid   acetylsalicylic acid   acetic acid Part I  Synthesis of Aspirin Mass of salicylic acid used (g)  2.029g Volume of acetic anhydride used (mL)  5ml Mass of acetic anhydride used (vol. × 1.08 g/mL)  5.4g Mass of aspirin synthesized (g)  3.256g Part II  Melting Temperature Data Melting temperature (°C)  133°C Part III  Salicylic Acid Standard Stock Solution Initial mass of salicylic acid (g)  0.210g Moles of salicylic acid (mol)  0.0147 mol Initial molarity of salicylic acid (M)  0.724 M Part III  Beer’s Law Data for Salicylic Acid Standard Solutions Trial Concentration (M) Absorbance Water (mL) 1  10  0.301 0…

What are the safety hazards of these chemicals  Acetic anhydride (108-24-7) Formic acid (64-18-60) Benzotriazole (95-14-7) N-Formylbenzotriazole (72773-04-7)

Methyl benzoate can be synthesized by a Fisher Esterification reaction, and then this ester can be used as a starting material in the grignard synthesis of triphenyl carbinol. Suppose that in the synthesis of methyl benzoate, a student started with 12 grams of benzoic acid and 29.86 ml of methanol. After finishing the preparation of the ester, 7.63 grams of methylbenzoate was obtained, and the benzoic acid reacted completely. What is the percent yield of the ester? ( density methanol = 0.791 g/ml, methanol = 32.04 g/mol, methyl benzoate = 136.15 g/mol, benzoic acid = 122.12 g/mol )

Upon completion of a chemical reaction, you find you have a mixture of benzoic acid and ethyl benzoate. Propose a procedure to separate the ethyl benzoate from the mixture. You should look up the structures of benzoic acid and ethyl benzoate.

1) Hydrolysis of Methyl Salicylate: Methyl Salicylate (C8H8O3) + sodium Hydroxide (NaOH) -> sodium Salicylate ( NaC7H5O3) + Methanol (CH3OH) 2) Acidification of Sodium Salicylate: Sodium salicylate (NaC7H5O3) + HCL -> Salicylic acid (C7H603) + sodium chloride (NaCL) Could you find the theoretical yield for me? 2.15g of methyl salicylate was used. 25ml of sodium hydroxide (2m solution) was used for hydrolysis and 2ml of hydrochloric acid was used for the acidification. This produced a yield of 1.53g of salicylic acid.

Potassium sorbate is added as a preservative to certain foods to prevent bacteria and molds from causing food spoilage and to extend the foods’ shelf life. The IUPAC name of potassium sorbate is potassium (2E,4E)-2,4-hexadienoate. Draw a structural formula for potassium sorbate.

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In the 1880's, Acetanilide, sold under the name Antifebrin, was widely used as a pain reliever and fever reducer. However, it had many adverse side effects, including cyanosis as a result of methemoglobinemia. The toxic side effects were the result of a small portion of acetanilide being hydrolyzed to aniline. Acetanilide was discontinued and replaced with phenacetin. Later studies show that both acetanilide and phenacetin are metabolized to acetaminophen. This metabolite, which we know as Tylenol, is responsible for the analgesic and antipyretic properties. Part 1: Show a detailed arrow pushing mechanism of the acid catalyzed hydrolysis of acetanilide to aniline Part 2: Propose a synthesis of Acetaminophen from phenol NH NH NH Phenacetin inophen Acetanilide Attach File Browse Local Files Browse Content Collection

SYNTHESIS OF ESTERS VIA NUCLEOPHILIC ACYL SUBSTITUTION Write the chemical equation involved in the reaction between the excess acid and NaHCO3. Explain why NaHCO3 is preferred over NaOH for the neutralization of excess acid.  How was excess alcohol eliminated from the crude product.

Hydroxide acts as a nucleophile in protein degradation by hydrolysis of the peptide bond in water. Draw out an arrow pushing mechanism of the hydrolysis of a peptide bond. Identify the nucleophile and the electrophile in this reaction.

Select the correct products for the first reaction. The second question is select the correct product for the reaction (only one answer).