D Question 11 Identify all amines below that cannot be made via an azide synthesis (reaction with NaN3 followed by reduction by LAH). NH2 NH2 (a) (b) (c) -NH2 (d) -NH, (e) (f) NH2 (a) (b) (c) O (d) (e) (f) Question 12 What is an appropriate stepwise synthesis to carry out the conversion shown? "NH2 ; HNO3/H2SO4; Fe/HCl; NANO2/HCI/< 5°C; CUCN; Zn(Hg)/HCl; LIAIH4; 8. H3O* CH;CH,CI / AICI3' CH3CH2CI/AICI3; HNO3/H2SO4; Na2Cr207/H2SO4/H20; Fe/HCl; NANO2/HCl/< 5°C; CUCN HBr/heat; NaNO2/HCI/< 5°C; H2SO4; KMNO4/NaOH/H2O; H30" HNO3/H2SO4; Br2/FeBr3; Fe/HCl; NaNO2/HCI/< 5°C; CH3OH/heat ; Br2/AIBr3; Fe/HCI; NaNO2/HCI/< 5°c; CUCN; Zn(Hg)/HCI; LIAIH4; H30* CH;CH,CI / AICI3

D Question 11 Identify all amines below that cannot be made via an azide synthesis (reaction with NaN3 followed by reduction by LAH). NH2 NH2 (a) (b) (c) -NH2 (d) -NH, (e) (f) NH2 (a) (b) (c) O (d) (e) (f) Question 12 What is an appropriate stepwise synthesis to carry out the conversion shown? "NH2 ; HNO3/H2SO4; Fe/HCl; NANO2/HCI/< 5°C; CUCN; Zn(Hg)/HCl; LIAIH4; 8. H3O* CH;CH,CI / AICI3' CH3CH2CI/AICI3; HNO3/H2SO4; Na2Cr207/H2SO4/H20; Fe/HCl; NANO2/HCl/< 5°C; CUCN HBr/heat; NaNO2/HCI/< 5°C; H2SO4; KMNO4/NaOH/H2O; H30" HNO3/H2SO4; Br2/FeBr3; Fe/HCl; NaNO2/HCI/< 5°C; CH3OH/heat ; Br2/AIBr3; Fe/HCI; NaNO2/HCI/< 5°c; CUCN; Zn(Hg)/HCI; LIAIH4; H30* CH;CH,CI / AICI3

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

Chapter18: Functional Derivatives Of Carboxylic Acids

Section: Chapter Questions

Problem 18.40P

See similar textbooks

Similar questions

The following three derivatives of succinimide are anticonvulsants that have found use in the treatment of epilepsy, particularly petit mal seizures. Q. Show how this same synthetic strategy can be used to prepare ethosuximide and methsuximide.
Safrole, which is isolated from sassafras (Problem 21.33), can be converted to the illegal stimulant MDMA (3,4- methylenedioxymethamphetamine, “Ecstasy”) by a variety of methods. (a) Devise a synthesis that begins with safrole and uses a nucleophilic substitution reaction to introduce the amine. (b) Devise a synthesis that begins with safrole and uses reductive amination to introduce the amine.
Devise a synthesis of benzocaine, ethyl p-aminobenzoate (H2NC6H4CO2CH2CH3), from benzene, organic alcohols, and any needed organic or inorganic reagents. Benzocaine is the active ingredient in the topical anesthetic Orajel (Section 18.15C).
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?
17.36 Tamoxifen is an estrogen receptor modulator that is used in the treatment of breast cancer. Provide the missing reagents and the structure of compound A in the synthesis of tamoxifen. Page 707 HO (CH3)2N 1. C,H,MgBr 2. H + Compound A (CH3)2N Tamoxifen
Rank the following compounds in order of increasing basicity: I. p-nitroaniline III. N-methylaniline II. p-aminobenzaldehyde IV. p-methylaniline
Ibufenac, a para-disubstituted arene with the structureHO2CCH2C6H4CH2CH(CH3)2 , is a much more potent analgesic thanaspirin, but it was never sold commercially because it caused livertoxicity in some clinical trials. Devise a synthesis of ibufenac frombenzene and organic halides having fewer than five carbons.
Devise a synthesis of benzocaine, ethyl p-aminobenzoate(H2NC6H4CO2CH2CH3), from benzene, organic alcohols, and any neededorganic or inorganic reagents. Benzocaine is the active ingredient in thetopical anesthetic Orajel
What carboxylic acid and amine are needed to synthesize the pain reliever phenacetin? Phenacetin was once a component of the over-the-counter pain reliever APC (aspirin, phenacetin, caffeine), but it is no longer used because of its kidney toxicity.
Maraviroc, a drug used to treat HIV, is prepared by reductive amination of aldehyde A with amine B. What is the structure of maraviroc, if the most basic N atom of amine B is used in reductive amination?