Choose reagents from the following table to convert oleic acid to 18-pentatriacontanone, CH₂(CH₂)16CO(CH₂)16CH3 (structure below).List reagents by letter in the order used.Example: aba CrO3/H3O+b Br₂/CH₂Cl₂сdH3O*/H₂O1. NaOCH32. H3O*, heatSynthetic pathwayReagentse CH3OH/HCIhLi/NH3KMnO4/H₂O*1. LIAIH4/dry ether2. H30*/H₂Oi 1.03jH₂/Pdk2. Zn/CH3CO₂HINaNH 2NH31. Br₂/PBr32. H₂O

Answered: Image /qna-images/answer/27cc22bd-5b1d-4eec-a574-abfa4c92090e.jpg

Peagents from the following table to convert oleic acid to 18-pentatriacontanone, CH₂(CH₂)16CO(CH2)16CH3 (structure below). List reagents by letter in the order used. Example: ab a CrO3/H30* bBr₂/CH₂Cl₂ C d H3O*/H₂O 1. NaOCH3 2. H3O*, heat e f 9 h Reagents CH₂OH/HCI Li/NH3 KMnO4/H₂O* 1. LIAIH4/dry ether 2. H30*/H2₂0 i 1.03 j k 1 2. Zn/CH3CO₂H H₂/Pd NANH, NH3 1. Br2/PBr3 2. H₂O

Peagents from the following table to convert oleic acid to 18-pentatriacontanone, CH₂(CH₂)16CO(CH2)16CH3 (structure below). List reagents by letter in the order used. Example: ab a CrO3/H30* bBr₂/CH₂Cl₂ C d H3O/H₂O 1. NaOCH3 2. H3O, heat e f 9 h Reagents CH₂OH/HCI Li/NH3 KMnO4/H₂O* 1. LIAIH4/dry ether 2. H30*/H2₂0 i 1.03 j k 1 2. Zn/CH3CO₂H H₂/Pd NANH, NH3 1. Br2/PBr3 2. H₂O

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

Chapter10: Alcohols

Section: Chapter Questions

Problem 10.50P

See similar textbooks

Similar questions

Predict the products, if any, of the following reactions. 20-35 (a) ascorbic ac (1) LiAlH4 -COOH (2) H3O+ (b) (1) NaCN CH₂Br (2) H3O+, heat (c) (1) SOCl2 (d) KMnO4, H₂O oct-4-yne (warm, concd.) (2) AlCl3 COOH (e) CH₂OH Na2Cr2O7, H2SO4 (f) Ph (1) BH3.THF CH3CH2-CH-COOH (2) H₁₂O+
10-Bromo-a-chamigrene, a compound isolated from marine algae, is thought to be biosynthesized from y-bisabolene by the following route: "Br* Bromonium Cyclic carbocation -H*) Base ion Bromo peroxidase Br y-Bisabolene 10-Bromo-a- chamigrene
(A) moose the correct product. 1. NaGE, Ero 2. H₂0, A 食。 CO₂ Et -CO₂E7 (B) Coret 31. Choose the best reagents. & 4 (A) 1. LAH; H₂0 2. CHz | 3. H₂0/H+ (B) 1. NaOH, -78% 2. CH31 3. H₂0/H (C) 1. LDA, -78%℃ 2. CH31 3. H₂₂0/H+ 1. Nah, 0°C 2. CH31 3. H₂2₂0/H+* (<) Colt (D)
Provide the reagents necessary to carry out the following conversion: 4-methyl-cyclohexanol -------> 4-methyl- cyclohexanone O KMNO4/NAOH/H20 peroxyacetic acid O Br2, CCl, O NazCr207/H2SO2/H2O O OsO4
Several sulfonylureas, a class of compounds containing RSO2NHCONHR, are useful drugs as orally active replacements for injected insulin in patients with adult-onset diabetes. These drugs decrease blood glucose concentrations by stimulating b cells of the pancreas to release insulin and by increasing the sensitivity of insulin receptors in peripheral tissues to insulin stimulation. Tolbutamide is synthesized by the reaction of the sodium salt of p-toluenesulfonamide and ethyl N-butylcarbamate . Propose a mechanism for this step.
20. Identify the product for each step in the following reaction sequence. Write complete equations showing the structure of all reactants and products for each step. (a) Isopropyl benzene + NBS/heat ---------->A (b) A+ t-BuOK ---------> B (c) B + 1)BH3 followed by 2)H2O2/NaOH -----> C (d) C + PCC ------> D
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?
Choose the best reagents from the list provided below for carrying out the following conversion. Match the reagent with the step number. HCl (aq), Zn(Hg) KMnO4, H3O+ CH3Cl, AlCl3 HNO3, H2SO4 Cl2, FeCl3 fuming sulfuric acid
Two possible methods to synthesize carboxylic acids are shown below. For the synthesis of cyclopentanecarboxylic acid from bromocyclopentane, which of the following statements is true? cyclopentanecarboxylic acid: R KCN H2O, HCI, heat Method I RBr RCO,H Method II Mg/diethyl ether RBr (1) CO2 RCO,H (2) H,0* A) Neither method I nor II would work. B) Only method I would work. C) Only method II would work. D) Both method I and II would work. O A MacBook Pro G Search or type URL 23 $4 6. 7. 8. R
Which set of reagents would be appropriate to synthesize bromobenzene from benzene? 1. HNO3 in H2SO4; 2. H2Cr04 and heat 1. H2CrO4 and heat; 2. H2 Pd/C Br2 and FeBr3 1. CH3CH2CHCI and AICI3; 2. H204 and heat 4B12 and Fe Heat and Br2 Br2, HCI
a. Enamines formed from the cyclic secondary amine pyrrolidine are important intermediates in the synthesis of 1,5-diketones. On the structures provided below, formation of an enamine from cyclopentanone and piperidine. draw the curved arrows for the reaction mechanism for the acetic acid-catalyzed H H H H eo N H H H3C- isod 1916w Proton Transfer (PT) 000 'H HO :01H SHO 6: HO H H 8²8-- H H 12.H food to shujounte sitt allarWm H OH M HO N