b) Pyrrole and indole both react with the reagents shown below to give compounds Eand F respectively.Reagents:РОС3, NazCОз, Н2О`N'HEF(i)(ii)(iii)Show how the electrophile is generated.Account for the regioselectivity observed.Complete the mechanism for the formation of compound F.Z-I

Answered: Image /qna-images/answer/386441e8-f0b0-40a8-a2c0-16ae1ec54dfb.jpg

b) Pyrrole and indole both react with the reagents shown below to give compounds E and F respectively. Reagents: POC3, Na2C03, H2O `N' 'N E F (i) (ii) Show how the electrophile is generated. Account for the regioselectivity observed. Complete the mechanism for the formation of compound F. (iii) Z-I

b) Pyrrole and indole both react with the reagents shown below to give compounds E and F respectively. Reagents: POC3, Na2C03, H2O `N' 'N E F (i) (ii) Show how the electrophile is generated. Account for the regioselectivity observed. Complete the mechanism for the formation of compound F. (iii) Z-I

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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(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).
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.
(a) 1-methylcyclopentene B can be prepared by an intramolecular Wittig reaction from A. Propose a plausible arrow-pushing mechansim for this the transformation from A to B. (b) Propose a synthesis to convert 1-methylcyclopentene B to the cyclic ester C. Show all intermediates, and reagents necessary for each step.
7. Answer ALL parts of this question. (a) Answer BOTH parts of this question Reaction of the carboxylic acid below (Scheme Q7(a)) with bromine in the presence of dibenzoylperoxide gives rise to an unstable compound A (CSH&BR2O2) that gives a stable compound B on treatment with a base. The stable compound has IR peaks at 1735 and 1645 cm and NMR peaks at &H (ppm) 6.18 (1H, s), 5.00 (2H, s) and 4.18 (2H, s). Br. Base (PhCO, Scheme Q7(a) (1) What is the structure of the unstable compound A? (i) Show the mechanisms for the two steps in the reaction (b) Answer BOTH parts of this question Tetraphenylporhyrin (TPP) is a singlet sensitiser that reacts with oxygen and can engage in pericyclic reactions (Scheme Q7(b). OH O. TPP hv Scheme Q7(b) (i) Explain the difference between a singlet and a triplet state. (ii) Show the mechanism for the reaction shown in Scheme 07(b) (ii) Consider the below reaction (figure Q7(c)), Show the structure of the product (C) anc the mechanism Scheme Q7 (b)
Treatment of 1,3,6-cyclononatriene (Compound 1), or its dimethyl derivative (Compound 2), with potassium amide (KNH₂) in liquid ammonia results in the formation of anion 1a or 2a, respectively (J. Am. Chem. Soc. 1973, 95, 3437-3438): 9 15.85a 2 6 3 4 5 Compound 1 (R=H) Compound 2 (R=CH3) * You answer is incorrect. KNH₂ KNH₂ 1a (anion) 2a (anion) Of the following, which is NOT one of the four resonance structures of 1a?
Reaction of toluene with bromine gas and AlBr3 will produce two major products of aryl halides which is compound K and L (C;H¬B1). Toluene is then reacted with acidified KMnO4 to produce a compound M (C;H6O2). Friedel-Craft acylation of compound M with CH3CH2COCI will produce compound N (C10H10O3). a) Outline the structure of compound K, L, M and N. b) Nitration reaction of compound M and toluene will be at different rate. Predict which compound will undergo nitration reaction at faster rate.
(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
Identify products A and B from the given 1H NMR data. Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1H) ppm. What is the structure of B?
2) Cinnamaldehyde is one of the primary constituents of cinnamon oil and contributes significantly to the odor of cinnamon. Starting with benzaldehyde and using any other necessary reagents, show how you might prepare cinnamaldehyde. Give your answer as a scheme. Ay H cinnamaldehyde
Spirocyclic compounds, such as compound 3, are made and used by insects for the purposes of communication. The first step of a synthesis of compound 3 involves treatment of (S)-1,2-epoxypropane (compound 1) with lithium acetylide, followed by acid workup, to give compound 2, as shown below (J. Org. Chem. 2005, 70, 3054-3065). Identify the structure of compound 2 and provide a mechanism for its formation. (Hint: The carbon-lithium bond reacts in a way that is similar to the carbon-magnesium bond of a Grignard reagent.) 1 13.17 a 1) Li—= 2) H₂O+ нас!!!!!! C5H8O Edit Drawing 2 Ž Modify the given structure of the starting material to draw the major product. an 3
(−)-Hyoscyamine, an optically active drug used to treat gastrointestinal disorders, is isolated from Atropa belladonna, the deadly nightshade plant, by a basic aqueous extraction procedure. If too much base is used during isolation, optically inactive material is isolated. (a) Explain this result by drawing a stepwise mechanism. (b) Explain why littorine, an isomerisolated from the tailower plant in Australia, can be obtained optically pure regardless of the amount of base used during isolation.
2. (a) Ozonolysis of compound A, C,H12 gave two products B and C. Further analysis of these two compounds of B and C, showed positive results with 2,4-dinitrophenylhydrazine. Compound B reacts with Tollens' reagent while compound C does not indicate any positive result to the same reagent. However, both B and C gave same positive results with iodoform test. (i) By writing all the chemical equations involved, identify A, B and C.