4.35 Formulate the reaction of cyclohexene with (i) Br2 and (ii) meta-chloro- peroxybenzoic acid followed by H30+. Show the reaction intermediates and the final products with correct cis or trans stereochemistry.
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- 19. (a) Show the structure of all reactants and products for the bromination of 1,2 dimethylcyclopentene. Show the proper stereochemistry of the products. 1,2-dimethylcyclopentene + Br2/CCl4-----> Products (b) Show the mechanism of the reaction in (a) above.Treatment of propadiene (an allene) with hydrogen bromide produces 2-bromopropene as the major product. This suggests that the more stable carbocation intermediate is produced by the addition of a proton to Br HBr. H2C=C=CH, H3C CH2 a terminal carbon rather than to the central carbon. Propadiene 2-Bromopropene (a) Draw both carbocation intermediates that can be produced by the addition of a proton to the allene. (b) Explain the relative stabilities of those intermediates. Hint: Draw the orbital picture of the intermediates and consider whether the CH, groups in propadiene are in the same plane.The Wittig reaction can be used for the synthesis of conjugated dienes, as, for example, 1-phenyl-1,3-pentadiene. -CH=CHCH CHCH, 1-Phenyl-1,3-pentadiene Propose two sets of reagents that might be combined in a Wittig reaction to give this conjugated diene.
- Pure (S)-2-bromo-2-fluorobutane reacts with methoxide ion in methanol to give a mixture of (S)-2-fluoro-2-methoxybutane and three fluoroalkenes.(a) Use mechanisms to show which three fluoroalkenes are formed9. (a) With the help of orbital correlation diagram predict the conditions of 4+2r system. (b) Using PMO approach, discuss the reaction conditions for 4x electrocyclic reaction. (c) What are 1,3-dipolar cycloaddition reactions? Give examples. 10. Predict the product under the given reaction conditions and propose mechanism. C (b) A OMe O OMe OMe A in Decanea) What product is formed from the [1,7] sigmatropic rearrangement of a deuterium in the following triene? (b) Does this reaction proceed in a suprafacial or antarafacial manner under thermal conditions? (c) Does this reaction proceed in a suprafacial or antarafacial manner under photochemical conditions?
- Elimination of HBr from 2-bromobutane affords a mixture of 1-butene and 2-butene. With sodium ethoxide as base, 2-butene constitutes 81% of the alkene products, but with potassium tert-butoxide, 2-butene constitutes only 67% of the alkene products. Offer an explanation for this difference.Give reasons: (i) C—Cl bond length in chlorobenzene is shorter than C—Cl bond length in CH3—Cl.(ii) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.(iii) SN1 reactions are accompanied by racemization in optically active alkyl halides2- Give the product for the addition of chlorine when HCl reacts with 3-Hexyne in acetic acid (CH3COOH). Show the correct stereochemistry, (is the product Z or E isomer). Identify the product in the following reaction: CH3CH₂CH₂C=CH + 2Cl₂ 3- What products are obtained by the hydration of the following Alkyne: CH3CH₂CH₂C=CCH₂CH₂CH3 1 ?
- Show each step of the reaction mechanism with arrow pushing of the reaction of 2,3 - Dihydrofuran reacts with acrolein to give C7H1002; reaction of this with aq. H2NOH/HCI gives a pyridine ch8 21 Hetero Diels-Alder cycloaddition H₂NOH, HCI No final oxidation required using H₂NOH N (CH2)2OH (CH2)2OH Synthon for a 1,5-dialdehydeAlkylation of benzene with 1-chlorobutane in the presence of AlCl3 gave not only the expected butylbenzene product but also, as a major product, (1-methylpropyl)benzene. Write an equation for the reaction Propose a mechanism to account for the formation of butylbenzene Propose a mechanism to account for the formation of (1-methylpropyl)benzenePoly and B-Ryan are asked by their supervisor to synthesize (1R,3R)-1-chloro-1,3- dimethylcyclopentane. To accomplish their syntheses, Poly chooses to start from a trisubstituted alkene while B-Ryan chooses to start from a disubstituted alkene isomer. Poly's synthesis provides a mixture of isomers while B-Ryan's provides two stereoisomers. Both synthetic approaches are shown below. Me Me, Me, .CI Me HCI A B-Ryan's Synthesis Me 'CI + 75% 25% Ме Me Me Me... Me B Me C HCI A Poly's Synthesis -Me Ме 'CI 'CI + + Me.. .CI + a trace mixture ; of constitutional D Ме chloroalkane isomers Using your mechanistic knowledge of alkene reactions: (a) Explain the selectivity (regio and stereo) observed in B-Ryan's synthesis. (b) Propose a mechanism that accounts the formation of isomer C in Poly's synthesis. (c) Draw the major stereoisomer(s) formed in the "trace mixture of constitutional isomers" isolated in Poly's synthesis. 9.