After performing all of the necessary calculations, the appropriate glassware and reaction conditions must be determined. The reaction being conducted produces 1 molar equivalent of HCl as a by-product (Figure 2.2), and must be performed under anhydrous conditions because p-nitrobenzyl chloride is hydrolyzed to p-nitrobenzoic acid as per the following reaction H20 CI HO. O2N O2N What is the appropriate amount of triethylamine that must be added into this reaction to ensure the HCI produced is mopped up to keep the 2,6-dimethylamine nucleophilic? A catalytic amount 0.5 molar equivalents O 1.0 molar equivalent 10 molar equivalents

After performing all of the necessary calculations, the appropriate glassware and reaction conditions must be determined. The reaction being conducted produces 1 molar equivalent of HCl as a by-product (Figure 2.2), and must be performed under anhydrous conditions because p-nitrobenzyl chloride is hydrolyzed to p-nitrobenzoic acid as per the following reaction H20 CI HO. O2N O2N What is the appropriate amount of triethylamine that must be added into this reaction to ensure the HCI produced is mopped up to keep the 2,6-dimethylamine nucleophilic? A catalytic amount 0.5 molar equivalents O 1.0 molar equivalent 10 molar equivalents

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter22: Carbonyl Alpha-substitution Reactions

Section22.SE: Something Extra

Problem 63AP: As far back as the 16th century, South American Incas chewed the leaves of the coca bush,...

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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?
2. a) Provide the missing reaction product(s), or conditions to the following reactions. ACO + hv DCM, -55 °C NaOH (aq) C11 H1602
Which of the following reactions will synthesize phenol from benzene? 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) warm H2SO4 and H2O 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) CuCN; 5) dilute acid and heat 1) Acetyl chloride & AlCl3; 2) bleach 1) Ph-N2+ + KI; 2) BrMgCH=CH2 in ether, followed by H3O+; 3) warm, conc'd KMnO4 1) Cl-CH(CH3)-CH2CH2CH3 + FeBr3; 2) hot, conc'd KMnO4
(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) Ph Ph 8*8 Ph THF A 1 Santande B H₂SO4 100 °C 3 OH Using curly arrows, provide full mechanistic details accounting how methylenecyclohexane 2 was synthesised according to both Methods A and B.
Give the major organic product(s) for each of the following reactions (a) + H2 1. (CF3CO0)2Hg. CH3OH (b) 2, NABH4
Predict the product of the following reactions. (a) 1. NaOEt, EtOH, heat 2. H3O+ quench (b) Pho O O OEt OMe 1. NaOMe, MeOH, heat 2. H3O+ quench
a.) Give an acceptable name for compound C. (b) Draw the organicproducts formed when C is treated with each reagent: [1] H3O+; [2] −OH,H2O; [3] CH3CH2CH2MgBr (excess), then H2O; [4] LiAlH4, then H2O.
Provide the structure of the major product(s) of the followings organic reactions: a) b) c) d) e) f) h) -CEC -CECH -CECH -CECH Na CH3CH₂-CEC-CH3 -CECH NaNH, H₂ Lindlar's catalyst Na NH3 HBr (1 equivalent) HgSO4 H₂SO4, H₂O Sia₂BH H₂O₂ он 1) 0₂ 2) H₂O Br H30
22). What is the major product of the following reactions? (A) (B) Br 1) NaCN 2) CH3MgBr 3) H30*/H₂O (C) LOH (D) CN
(a) Give an acceptable name for each compound, (b) Draw the organic products formed when A or B is treated with each reagent: [1] H3O+; [2] −OH, H2O; [3] CH3CH2CH2MgBr (excess), then H2O; [4] LiAlH4, then H2O.
Question 2 (a) Given and Scara were given a task of synthesising (2-methylprop-1-enyl)cyclohexane 2 (A potential TB drug). After a brief discussion with each other, Given proposed Method A to synthesise 2 from cyclohexanecarbaldehyde 1 while Scara proposed Method B that started from hydroxymethylcyclohexane 3. When designing a synthetic route for drug molecule, you have to make sure the synthetic process is as efficient as possible (e.g. few synthetic steps, mostly making one product and more). (1) T nunum 1 THF A Ph Ph Ph B 1. PCC 2. isopropyl magnesium vromide 3. H₂SO4 100 °C OH Using curly arrows, provide full mechanistic details to explain how method A will proceed.
Question 2 (a) Given and Scara were given a task of synthesising (2-methylprop-1- enyl)cyclohexane 2 (A potential TB drug). After a brief discussion with each other, Given proposed Method A to synthesise 2 from cyclohexanecarbaldehyde 1 while Scara proposed Method B that started from hydroxymethylcyclohexane 3. When designing a synthetic route for drug molecule, you have to make sure the synthetic process is as efficient as possible (e.g. few synthetic steps, mostly making one product and more). 1 THF A Ph Ph B 3 1. PCC 2. isopropyl magnesium vromide 3. H₂SO4 100 °C OH After analyzing both of these methods, draw any one possible alkene product other than (2-methylprop-1-enyl)cyclohexane 2?Use mechanistic details to support your answer