The analgesic meperidine (Demerol) was developed in the search for analgesics with- out the addictive effects of morphine. As shown in these structural formulas, it repre- sents a simplification of morphine's structure. H.C. H,C. CH3 (redraw) НО OH Morphine Meperidine Meperidine is prepared by treating phenylacetonitrile with one mole of bis(N-2- chloroethyl)methylamine (a nitrogen mustard) in the presence of two moles of sodium hydride to give (A). Refluxing (A) with concentrated sodium hydroxide followed by neutralization of the reaction mixture with dilute HCl gives (B). Treating (B) with ethanol in the presence of one equivalent of HCl gives meperidine as its hydrochloride salt. N-CH, 1. NaOH C13H16N2 2 NaH 2. HCI (A) Phenylacetonitrile ELOH, HCI C13H1,NO, C5H2NO, · HCI (В) Meperidine hydrochloride

The analgesic meperidine (Demerol) was developed in the search for analgesics with- out the addictive effects of morphine. As shown in these structural formulas, it repre- sents a simplification of morphine's structure. H.C. H,C. CH3 (redraw) НО OH Morphine Meperidine Meperidine is prepared by treating phenylacetonitrile with one mole of bis(N-2- chloroethyl)methylamine (a nitrogen mustard) in the presence of two moles of sodium hydride to give (A). Refluxing (A) with concentrated sodium hydroxide followed by neutralization of the reaction mixture with dilute HCl gives (B). Treating (B) with ethanol in the presence of one equivalent of HCl gives meperidine as its hydrochloride salt. N-CH, 1. NaOH C13H16N2 2 NaH 2. HCI (A) Phenylacetonitrile ELOH, HCI C13H1,NO, C5H2NO, · HCI (В) Meperidine hydrochloride

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.63P

See similar textbooks

Similar questions

What changes would be made to separate the two isomeric pinene (α and β), bp 156 oC and 167 oC respectively that are the major constituents of commercial turpentine?
An unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent ofH2 over a palladium catalyst. Hydrocarbon A also reacts with OsO4 to give diol B. When oxidized with KMnO4 in acidic solution, A gives two fragments. One fragmentis propanoic acid, CH3CH2CO2H, and the other fragment is ketone C. What are thestructures of A, B, and C? Write all reactions and show your reasoning.
After graduating from your PhD, you are now working as a post-doctoral researcher in BASF , the world’s largest multinational chemical company. The management of your R&D department decided to look at the potentiality of chloroform-methanol mixture in removing the lipids of various biological systems. Your boss, a senior scientist at your department, thinking about the hydroxyl group on the alcohol and thet hree chlorines on the CHCl3 , suggested that the mixture is probably non-ideal. Being one of her brightest colleagues, she then tasked you to graph the partial molar enthalpies of the chloroform methanol mixture as a function of mole fraction. Ardently, you accepted the challenge and went back to your office. After several hours of searching, you finally come up with enthalpy of mixing data at 50oC fort his mixture (See the picture). Please provide the graphs that the boss has asked you for. Put both curves on the same graph. Note: provide your excel file for this
In addition to HCl, what is the product of the reaction of aprimary amine with an acid chloride? Draw the structureof that product and describe its features
60% aqueous acetonitrile is isoelutropic with ____% aqueous methanol?
(a) Draw the three isomers of benzenedicarboxylic acid.(b) The isomers have melting points of 210 °C, 343 °C, and 427 °C. Nitration of the isomers at all possible positions was once used to determine their structures. The isomer that melts at 210 °C gives two mononitro isomers. The isomer that melts at 343 °C gives three mononitro isomers. The isomer that melts at 427 °C gives only one mononitro isomer. Show which isomer has which melting point.
The compound acetophenone has a very similar molar mass to that of benzoic acid and benzamide. However, acetophenone has a much lower m.p. (20 °C) than both such that, by contrast, it is a liquid at room temperature. By considering intermolecular forces and comparing functional group structure, account for this big difference in physical properties.
An unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent of H2 over a palladium catalyst to give hydrocarbon B. Hydrocarbon A also reacts with OsO4 to give the glycol C. When oxidized with KMnO4 in acidic solution, A gives two fragments. One fragment is propanoic acid, CH3CH2COOH, and the other fragment is ketone D (R2C=O). What are the structures of A, B, C and D? Write all reactions.
Formaldehyde, H2C=O, is known to all biologists because of its usefulness as a tissue preservative. When pure, formaldehyde trimerizes to give trioxane, C3H6O3, which, surprisingly enough, has no carbonyl groups. Only one monobromo derivative (C3H5BrO3) of trioxane is possible. Propose a structure for trioxane.
Calculate the theoretical mass of benzil that can be reduced to hydrobenzoin using 100 mg NaBH4
7 Ethanoic acid has a melting point of 17 °C, ethanamide has a melting point of 81 °C, and ethanal has a melting point of -125 °C. Rationalize the differences in melting point between these three compounds.
An organic compound is analysed and found to contain 66.7% carbon, 11.2% hydrogen and 22.1% oxygen by mass. The compound boils at 79.6 C. At 100 C and 0.970atm, the vapour has a density of 2.28g/L. The compound has a carbonyl group and cannot be oxidized to a carboxylic acid. Suggest a structure for the compound.