Compound D contains nitrogen and produces a gas upon heating with aqueous NaOH. When the resulting solution is acidified and extracted with ether, compound E is isolated. Compound F is formed when compound E is heated with acidic methanol. Reduction of compound F with LiAlH., followed by acid workup yields methanol and 4-methyl-1-pentanol. What are the structures of compounds D, E and F? Show these compounds within the synthetic route described above (no mechanisms are required). Provide a curved-arrow (arrow pushing) mechanism for the transformation below. Show all movement of electrons, intermediates, and formal charges. CH₂O-K+, CH₂OH Br

Compound D contains nitrogen and produces a gas upon heating with aqueous NaOH. When the resulting solution is acidified and extracted with ether, compound E is isolated. Compound F is formed when compound E is heated with acidic methanol. Reduction of compound F with LiAlH., followed by acid workup yields methanol and 4-methyl-1-pentanol. What are the structures of compounds D, E and F? Show these compounds within the synthetic route described above (no mechanisms are required). Provide a curved-arrow (arrow pushing) mechanism for the transformation below. Show all movement of electrons, intermediates, and formal charges. CH₂O-K+, CH₂OH Br

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 10.57P

See similar textbooks

Similar questions

(b) acid, HNO3 to produce compound L. The reaction of compound L with bromine, Br2 in the presence of iron tribromide, FeBr3 produced compound M. Benzene also undergoes Fridel-crafts alkylation reaction with chloroethane, CH;CH2CI using catalyst N to produce compound P. Benzene, CeHe undergoes substitution reaction with concentrated nitric Benzena, CsHe menjalani tindak balas penukargantian dengan asid nitrik, HNO, pekat untuk menghasilkan sebatian L. Tindak balas sebatian L dengan bromin, Brz dengan kehadiran ferum tribromida, FeBrs menghasilkan sebatian M. Benzena juga menjalani tindak balas alkilasi Fridel-crafts dengan kloroetana, CH3CH2CI dengan menggunakan pemangkin N untuk menghasilkan sebatian P. (i) Draw the structural formula of L, M and P. Lukiskan formula struktur bagi sebatian L, M dan P. (ii) State catalyst N. Nyatakan pemangkin N. (iii) Show the formation of electrophile that will be reacted with benzene for the formation of compound P.
V) Outline a synthesis of the following compound from benzene and other appropriate organic or inorganic reagents. ? CH3 ? CO2H Excess ?
Provide the structure of the major organic product of the following reaction and? explain the stereochemistry which results in this product. 2-Pentanol reacting with 1.) PBr3, pyridine 2.) NaCN
The following two isomeric ketones were among the 68 compounds isolated from the steam-distilled volatile oil of fresh and air-dried marijuana buds (J. Nat. Prod. 1996, 59, 49–51). Propose a separate synthesis for each of these two compounds using only disubstituted alkenes containing four carbon atoms as starting materials.
Answer ALL parts. (a) Treatment of enone C with tetrabutylammonium fluoride leads to the formation of heterocycle D. 2 steps BU4NF C9H1602 A + B D OSIME,tBu (i) Enone C can be prepared from alkyne A and aldehyde B in two steps via a gold-catalysed reaction. Identify A and B and provide reagents/conditions for a synthesis of C. (ii) Give the structure of D and classify the ring-closing reaction for its formation from C according to Baldwin's rules (iii) Sketch the key molecular orbitals involved in the ring-closing reaction in part (ii) and hence explain whether the reaction is favourable or unfavourable.
Compound A reacts with 1 molar equivalent(s) of hydrogen upon catalytic hydrogenation. A undergoes reaction with ozone, followed by Zn treatment, to give: Propose a structure for A.
Following are the steps in the industrial synthesis of glycerin. Provide structures for all intermediate compounds (AD) and describe the type of mechanism by which each is formed.
Quinapril (trade name Accupril) is used to treat high blood pressure andcongestive heart failure. One step in the synthesis of quinapril involvesreaction of the racemic alkyl bromide A with a single enantiomer of theamino ester B. Given the structure of quinapril, which one of these two products isneeded to synthesize the drug?
Ozonolysis of compound D will produce compound E and compound F as products. Hydrationof compound D will produce compound G as major product. Compound D is a major productobtained from dehydrohalogenation of 2-chloro-3-methylbutane. a) Identify the structural formula for compound D, E, F and G.b) Suggest suitable reagent(s) and condition(s) needed for dehydrohalogenation of 2-chloro-3-methylbutane
just need last answer Compound A has the formula C10H14. When treated with hydrogen and palladium, Compound A takes up 2 equivalents of H2, forming Compound B. When A is treated with ozone followed by zinc, Compound C forms with the formula C10H1404. Compund C is a symmetric structure with four identical aldehyde groups. Provide structures for Compound A and the reaction products.
Suggest a synthesis for the following compound from the indicated starting materials and any other necessary organic and inorganic materials: from &
Treatment of compound C (molecular formula C9H12O) with PCC affordsD (molecular formula C9H10O). Use the 1H NMR and IR spectra of D todetermine the structures of both C and D.