Adding nitrite to meats prevents the growth of Clostridium botulinum, the bacteria responsible for botulism and nitrite prevents red meats from turning brown. N-nitrosopyrrolidine, an agent used to cause tumors in mice, is formed when bacon is "preserved' in nitrite and then fried. Propose a mechanism for the formation of N-nitrosopyrrolidine from pyrrolidine in an acidic solution of nitrite. (Look up structures as necessary.)

Adding nitrite to meats prevents the growth of Clostridium botulinum, the bacteria responsible for botulism and nitrite prevents red meats from turning brown. N-nitrosopyrrolidine, an agent used to cause tumors in mice, is formed when bacon is "preserved' in nitrite and then fried. Propose a mechanism for the formation of N-nitrosopyrrolidine from pyrrolidine in an acidic solution of nitrite. (Look up structures as necessary.)

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 21.62P

See similar textbooks

Similar questions

Reaction of p-nitroaniline with sodium nitrite and hydrochloric acid at 0°C, followed by treatment with N,N-diethylaniline.
Propranolol, an antihypertensive agent used in the treatment of high blood pressure, can be prepared from 1-naphthol, epichlorohydrin, and isopropylamine using two successive nucleophilic substitution reactions. Devise a stepwise synthesis of propranolol from these starting materials.
How might you convert geraniol into either ethyl geranylacetate or geranylacetone?
As far back as the 16th century, South American Incas chewed the leaves of the coca bush, Erythroxylon coca, to combat fatigue. Chemical studies of Erythroxylon coca by Friedrich WĂ¶hler in 1862 resulted in the discovery of cocaine, C17H21NO4, as the active component. Basic hydrolysis of cocaine leads to methanol, benzoic acid, and another compound called ecgonine, C9H15NO3. Oxidation of ecgonine with CrO3 yields a keto acid that readily loses CO2 on heating, giving tropinone. (a) What is a likely structure for the keto acid? (b) What is a likely structure for ecgonine, neglecting stereochemistry? (c) What is a likely structure for cocaine, neglecting stereochemistry?
Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to E. (d) Propose a mechanism for the conversion of F to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?
Propose a mechanism for the following reaction, an important step in the laboratory synthesis of proteins:
Ethylene oxide is the starting material for the synthesis of 1,4-dioxane. Propose a mechanism for each step in this synthesis.
Coumarin, a naturally occurring compound isolated from lavender, sweet clover, and tonka bean, is made in the laboratory from o-hydroxybenzaldehyde by the reaction depicted below. Draw a stepwise mechanism for this reaction. Coumarin derivatives are useful synthetic anticoagulants.
Reaction of p-nitroaniline with sodium nitrite and hydrochloric acid at 0 °C, followed by treatment with N,N-diethylaniline.
Propose a structural formula for the reagent used in Step 9 and show how it can be prepared from methylamine and ethylene oxide
What groups favor the nitration of benzene and what groups do not favor it?
Draw a stepwise mechanism for the following reactions, two steps in R. B. Woodward’s classic synthesis of reserpine in 1958. Reserpine, which is isolated from the extracts of the Indian snakeroot Rauwolfia serpentina Benth, was used at one time to manage mild hypertension associated with anxiety.