A hydrocarbon, A, with formula C11H16 undergoes hydrogenation with Pd to give product B, C11H22, and with Lindlar's catalyst to give product C, C11H18. Ozonolysis leads to a mixture of products including cyclohexanone and 4-oxobutanoic acid. Treatment with sodium amide (NaNH2) followed by bromoethane gives compound D, C13H20. Draw possible structures for A, B, C, and D. Structure of product C H₂, Lindlar's Structure of A 1. NaNHz 2. CH3CH2Br [1] Structure of product D

A hydrocarbon, A, with formula C11H16 undergoes hydrogenation with Pd to give product B, C11H22, and with Lindlar's catalyst to give product C, C11H18. Ozonolysis leads to a mixture of products including cyclohexanone and 4-oxobutanoic acid. Treatment with sodium amide (NaNH2) followed by bromoethane gives compound D, C13H20. Draw possible structures for A, B, C, and D. Structure of product C H₂, Lindlar's Structure of A 1. NaNHz 2. CH3CH2Br [1] Structure of product D

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

Chapter19: Enolate Anions And Enamines

Section: Chapter Questions

Problem 19.40P: Enamines normally react with methyl iodide to give two products: one arising from alkylation at...

See similar textbooks

Similar questions

Two isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H2O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. What is the isometric pair of A and B that corresponds?
Two isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H2O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. Which of the following isomeric pairs best match this data?
In an aqueous solution containing sodium bicarbonate, aniline reacts quickly withbromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions,however, and the yields (mostly m-nitroaniline) are poor.(a) What conditions are used for nitration, and what form of aniline is present under theseconditions?
(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.
The treatment of isoprene [CH2=C(CH3)CH=CH2] with one equivalent ofmCPBA forms A as the major product. A gives a molecular ion at 84 in itsmass spectrum, and peaks at 2850–3150 cm−1 in its IR spectrum. The 1HNMR spectrum of A is given below. What is the structure of A?
(c) Treating lactone B with two equivalents of phenylmagnesium bromide, followed by hydrolysis in aqueous acid, gives a compound with the molecular formula C18H22O2, as shown below. Propose a structural formula for this compound. 1. PhMgBr (2 eq.) 2. H'/H>O C18H2202 bj 1o 14 10I f6 40 & 3 4 00 (8)
Carototoxin is a natural pesticide produced by carrots, with formula C₁H2O. It undergoes hydrogenation with Pd to: give product A, C,H,O, and with Lindlar's catalyst to give product B, C,H2O. Ozonolysis followed by zinc leads to a mixture of methanal, octanal, 1,2-ethanedioic acid, 3-oxopropanoic acid, and 2-hydroxy-3-oxopropanoic acid. Draw possible structures for carototoxin, A, and B. Product B structure H2, Lindlar's Structure of carototoxin H2, Pd/C Product A structure
2-bromo-2-methylbutane undergoes hydrolysis reaction with water, H2O toform compound W. Compound X and compound Y are produced when 2-bromo-2-methylbutane undergoes elimination reaction with alcoholic ofsodium hydroxide, NaOH. (ii) What is the type of reaction involved in the formation of compound W? (iii) Identify the major product of the elimination reaction between compound Xand compound Y based on Zaitsev’s rule.
Predict the products, propose mechanisms for the reactions of carboxylic acidderivatives with reducing agents, alcohols, amines, and organometallic reagentssuch as Grignard, organolithium, and organocuprate reagents
а) Consider the reaction scheme below. PhLi HONH,, HCI A ELOH B (i) Deduce the structures of compounds A, D and intermediate C. (ii) Outline the mechanism for the conversion of A to B. b) Pyrrole and indole both react with the reagents shown below to give compounds E and F respectively. Reagents: POC13, NazCO3, H2O N. E F (i) (ii) (iii) Show how the electrophile is generated. Account for the regioselectivity observed. Complete the mechanism for the formation of compound F.
Stearolic acid, C18H32O2, yields stearic acid on catalytic hydrogenation and undergoes oxidative cleavage with ozone to yield nonanoic acid and nonanedioic acid. What is the structure of stearolic acid?
Q3] Diethyl malonate was treated with 2 moles of NaH followed by reaction with 1,4-dibromo-2-butene providing compound (A). Hydrolysis of compound A under heat 200 °C affording compound B; which was treated with PBr3 then with methanol/H+ affording C. The compound C then was exposed to ozonolysis conditions providing D. Finally two moles of ammonia react with D providing E. What are structures A..to .E?? A B C D E