Q4. Stabilized enolates and their surrogates. (a) Complete the following FOUR reaction schemes by drawing structures for the relevant stabilized enol, enolate or surrogate intermediates (A to D), and for the eventual organic products (E to H). (i) (ii) (iii) EtO Me SiCI, Et N NaOEt EtOH HCO₂Et, NaOEt EtOH A B C MeBr, TiCl 1. NaH 2. Mel 1. NaH 2. RBr E F

Q4. Stabilized enolates and their surrogates. (a) Complete the following FOUR reaction schemes by drawing structures for the relevant stabilized enol, enolate or surrogate intermediates (A to D), and for the eventual organic products (E to H). (i) (ii) (iii) EtO Me SiCI, Et N NaOEt EtOH HCO₂Et, NaOEt EtOH A B C MeBr, TiCl 1. NaH 2. Mel 1. NaH 2. RBr E F

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

Chapter11: Ethers, Epoxides, And Sulfides

Section: Chapter Questions

Problem 11.37P: Following are the steps in the industrial synthesis of glycerin. Provide structures for all...

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Q6. Enolates and their surrogates. (a) Rank the acidity of the following compounds from LEAST (left) to MOST (right) by entering the corresponding numbers in the boxes provided. 1 4 2 NaNH, CO₂Me 5 3 CHO (b) Complete the following reaction products by adding the correct bonds, atoms and charges, as necessary.
(d) Propose a reaction mechanism to account for the following reaction. AIC3
(4) Provide the reagents necessary to carry out the following synthesis. + enantiomer (A) (1) (i) BH3, (ii) H₂O2, NaOH; (2) NaOEt JATOT (B) (1) (i) BH3, (ii) H₂O2, NaOH; (2) TsCl, pyridine; (3) KOC(CH3)3 (C) (1) H3O+, (2) TsCl, pyridine, (3) KOC(CH3)3 (D) (1) HBr (no peroxides); (2) NaOEt
2. (a) The solvolysis reaction of compound 2A in acetic acid generated two major products 2B and 2C. Answer the following questions: (i) Draw the reaction mechanism for the for mation of 2B and 2C. (ii) Interestingly, researchers also observed the formation of 2D as a minor product. Propose a plausible mechanism to explain the formation of 2D. LOTS CH3COOH LOAC LOAC + AcO 2A 2B 20 2D (minor)
ال | A) B) ID) 5. (5) Provide the curved-arrow mechanism to account for the following imine formation through nucleophile addition. } H₂N acetic acid HO acetic acid
(c) Answer ALL parts (i) to (v). (i) Draw the structure of the enolate ion 5 formed by deprotonation of the ester 4 by the base NaOEt. (ii) Suggest a mechanism for the formation of the enolate 5 and for its reaction with ethanol to produce the diastereoisomeric ester 6. (iii) For each diastereoisomer (4 and 6) draw the two chair conformations (4 chair diagrams in total). (iv) By referring to your chair diagrams, predict which diastereoisomer (4 or 6) will predominate when equilibrium has been reached. (v) What do you think the result would be if the reaction was instead performed using NaOMe in MeOH? NaOEt O H он OEt OEt Ме. Me Ме Ме. Me- Me 4. 9
(iii) Rank the carbonyl compounds given below in terms of their relative reactivity with sodium borohydride. RT R CH3 CI (iv) Suggest two factors which combine to make the aldehyde react with sodium borohydride at a different rate from the ketone. (v) Based on electronegativity one might assume that the ester and acid chloride possess similar reactivity towards nucleophiles. Suggest why this turns out not to be the case (your answer should mention resonance and inductive effects).
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.
A key step in the hydrolysis of acetamide in aqueous acid proceeds by nucleophilic addition of * OH (a) H3O* to CH3Ĉ NH2 (b) H2O to CH3ČNH2 + OH +OH (c) H3O* to CH,ČNH2 (d) HO¯ to CH3CNH2
(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.
give the mechanism of the following reactions and explain why any selectivities occur.
From the given structures which is(a) an acid halide? (b) a secondary amide (c) an aldehyde incapable of self-aldol consensation?