Gamma(y)-amino butyric acid (GABA) is a neurotransmitter (a chemical that is used to send signals from one neuron to another) of the mammalian central nervous system. In order to understand how GABA works, conformationally restricted analogues, such as compound 1, have been made. During a synthesis of compound 1, compound 2 was subjected to allylic bromination using NBS and a radical initiator (AIBN) instead of light (Aust. J. Chem. 1981, 34, 2231-2236). H₂N. GABA CO₂H H₂N CO₂H dddd solddd 2 Modify the structures given below to draw all eight possible allylic bromides that can be formed when compound 2 undergoes allylic bromination, considering all possible regiochemical and stereochemical outcomes. You can use the single bond tool to add/remove pi bonds. CH₂ CO₂Et

Gamma(y)-amino butyric acid (GABA) is a neurotransmitter (a chemical that is used to send signals from one neuron to another) of the mammalian central nervous system. In order to understand how GABA works, conformationally restricted analogues, such as compound 1, have been made. During a synthesis of compound 1, compound 2 was subjected to allylic bromination using NBS and a radical initiator (AIBN) instead of light (Aust. J. Chem. 1981, 34, 2231-2236). H₂N. GABA CO₂H H₂N CO₂H dddd solddd 2 Modify the structures given below to draw all eight possible allylic bromides that can be formed when compound 2 undergoes allylic bromination, considering all possible regiochemical and stereochemical outcomes. You can use the single bond tool to add/remove pi bonds. CH₂ CO₂Et

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

Chapter23: Amines

Section: Chapter Questions

Problem 23.28P

See similar textbooks

Similar questions

Hypoglycin A, an amino acid derivative found in unripened lychee, is anacutely toxic compound that produces seizures, coma, and sometimesdeath in undernourished children when ingested on an empty stomach. (a) Draw the neutral, positively charged, and negatively charged forms of hypoglycin A. (b) Which form predominates at pH = 1, 6, and 11? (c) What is the structure of hypoclycin A at its isoelectric point?
Following is a retrosynthesis for the coronary vasodilator ganglefene. (a) Propose a synthesis for ganglefene from 4-hydroxybenzoic acid and 3-methyl-3-buten-2-one. (b) Is ganglefene chiral? If so, which of the possible stereoisomers are formed in this synthesis?
Naturally occurring compounds called cyanogenic glycosides, such as lotaustralin, release hydrogen cyanide, HCN, when treated with aqueous acid. The reaction occurs by hydrolysis of the acetal linkage to form a cyanohydrin, which then expels HCN and gives a carbonyl compound. (a) Show the mechanism of the acetal hydrolysis and the structure of the cyanohydrin that results. (b) Propose a mechanism for the loss of HCN, and show the structure of the carbonyl compound that forms.
The following transformation involves a series of four consecutive Heck reactions and the formation of the four-ring steroid nucleus (Section 26.4) as a racemic mixture. Propose structural formulas for the palladium-containing intermediates involved in this reaction.
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?
The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.
Following is an outline of the stereospecific synthesis of the “Corey lactone.” Professor E. J. Corey (Harvard University) describes it this way. “The first general synthetic route to all the known prostaglandins was developed by way of bicycloheptene intermediates. The design was guided by the requirements that the route be versatile enough to allow the synthesis of many analogs and also allow early resolution. This synthesis has been used on a large scale and in laboratories throughout the world; it has been applied to the production of countless prostaglandin analogs. Note: The wavy lines in compound C indicate that the stereochemistry of -Cl and -CN groups was not determined. Q. You have not studied the Baeyer-Villiger reaction (D to E). The mechanism involves nucleophilic reaction of the peroxyacid with the carbonyl followed by a rearrangement much like that involved in the hydroboration reaction ). Write a mechanism for this reaction.
Following is an outline of the stereospecific synthesis of the “Corey lactone.” Professor E. J. Corey (Harvard University) describes it this way. “The first general synthetic route to all the known prostaglandins was developed by way of bicycloheptene intermediates. The design was guided by the requirements that the route be versatile enough to allow the synthesis of many analogs and also allow early resolution. This synthesis has been used on a large scale and in laboratories throughout the world; it has been applied to the production of countless prostaglandin analogs. Note: The wavy lines in compound C indicate that the stereochemistry of -Cl and -CN groups was not determined. Q. The tributyltin hydride, Bu3SnH, used in the conversion of (H) to (I) reacts via a radical chain reaction; the first step involves a reaction with a radical initiator to form Bu3Sn?. Suggest a mechanism for the rest of the reaction.
Following is an outline of the stereospecific synthesis of the “Corey lactone.” Professor E. J. Corey (Harvard University) describes it this way. “The first general synthetic route to all the known prostaglandins was developed by way of bicycloheptene intermediates. The design was guided by the requirements that the route be versatile enough to allow the synthesis of many analogs and also allow early resolution. This synthesis has been used on a large scale and in laboratories throughout the world; it has been applied to the production of countless prostaglandin analogs. Note: The wavy lines in compound C indicate that the stereochemistry of -Cl and -CN groups was not determined. Q. What is the function of sodium hydride, NaH, in the first step? What is the pK a of cyclopentadiene? How do you account for its remarkable acidity?
Following is an outline of the stereospecific synthesis of the “Corey lactone.” Professor E. J. Corey (Harvard University) describes it this way. “The first general synthetic route to all the known prostaglandins was developed by way of bicycloheptene intermediates. The design was guided by the requirements that the route be versatile enough to allow the synthesis of many analogs and also allow early resolution. This synthesis has been used on a large scale and in laboratories throughout the world; it has been applied to the production of countless prostaglandin analogs. Note: The wavy lines in compound C indicate that the stereochemistry of -Cl and -CN groups was not determined. Q. By what type of reaction is (B) converted to (C)?