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- Treating cyclohexene with HBr in the presence of acetic acid gives bromocyclohexane (85%) and cyclohexyl acetate (15%). Br OCCH CH,COH + HBr Bromocyclohexane Cyclohexyl acetate (15%) Cyclohexene (85%) Propose a mechanism for the formation of the latter product.When the alkene A was treated first with Hg(OAc)2 in MeOH and second with NaBH4 the product was the ether B. Using curved arrows please give the mechanism for the first step of (Hg(OAc)2 in MeOH) this reaction, including any regioselectivity or stereoselectivity. H3C 1. Hg(OAc)2, MeOH H3C O-CH3 =CH2 ✓ -CH3 H3C 2. NaBH H3C A BExplain the mechanism of the following reaction using photodissociation: HCOOCH3 + hv -> CO + CH3OH
- Para-substituted product was produced when phenol reacts with cyclohexanecarbonyl bromide in the presence of AIB13. -Br Cyclohexanecarbonyl bromide (i) Outline the mechanism for this reaction. (ii) Draw the alternative substituted product formed.Provide the product and mechanism for the reaction: ОН Cro, H,SO, H,0Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.
- Alkylation 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)benzeneOne compound that contributes to the “seashore smell” at beaches in Hawai‘i is dictyopterene D', a component of a brown edible seaweed called limu lipoa. Hydrogenation of dictyopterene D' with excess H2 in the presence of a Pd catalyst forms butylcycloheptane. Ozonolysis with O3 followed by (CH3)2S forms CH2(CHO)2, HCOCH2CH(CHO)2, and CH3CH2CHO. What are possible structures of dictyopterene D'?Treating 2-methylpropene with methanol in the presence of sulfuric acid gives tert-butyl methyl ether. CH3 CH3 H,SO, CH,C=CH, + CH,OH CH,C-OCH, ČH3 Propose a mechanism for the formation of this ether.
- When cyclohexene is treated with m-chloroperbenzoic acid and H,0, trans-cyclohexane-1,2-diol is produced. Propose a mechanism for this reaction, accounting for the observed stereochemistry. Hint: Recall what a МСРВА + Enantiomer H2O "OH peroxyacid does to an alkene.Treatment of trans-2-chlorocyclohexanol with NaOH yields 1, 2-epoxy-cyclohexane, but reaction of the cis isomer under the same conditions yields cyclohexanone. Propose mechanisms for both reactions, and explain why the different results are obtained.Compound A Br₂, H₂O Compound B (C8H15BrO) + enantiomer CH₂O O Compound C + enantiomer Draw the structure of Compound B (watch out for stereochemistry), and mechanisms for its formation from Compound A, and its conversion to Compound C.