When the following alkene A was treated with sulfuric acid in water, the cyclohexanol product B was formed. Using curved arrows give the mechanism for this reaction, including any regioselectivity or stereoselectivity. CH3 CH3 OH H2SO4 CH3 A H₂O CH3 ៣ B
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- (a) What product(s) are formed when the E isomer of C6H5CH = CHC6H5 is treated with Br2, followed by one equivalent of KOH? Label the resulting alkene(s) as E or Z. (b) What product(s) are formed when the Z isomer of C6H5CH = CHC6H5 is subjected to the same reaction sequence? (c) How are the compounds in parts (a) and (b) related to each other?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.When treated with NaOH, the bromide below gives an alkene by the E2 mechanism, by elimination of the H atom indicated by the arrow: (a) Draw the Newman projection from which elimination takes place. (b) Draw the mechanism. (c) Draw the product with the proper stereochemistry. (d) Assign the proper stereochemical descriptor to the product. (e) Give the rate equation
- When cyclohexene is reacted with hydrobromic acid in acetic acid, the major product is bromocyclohexane. There is a small amount of cyclohexyl acetate formed. What is the mechanism that forms both compounds? What is the purification procedure that isolates both compounds?Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.When treated with NaOH, the bromide below gives an alkene by the E2 mechanism, by eliminationof the circled atoms: (a) Draw the Newman projection from which elimination takes place. (b) Draw the mechanism. (c) Draw the product with the proper stereochemistry. (d) Assign the proper stereochemical descriptor to the product. (Z, E? Trans,CiS?) (e)What would happen to the stereochemistry of the product if the enantiomer of the starting material were used inthe reaction?
- When (S)-5-methyl-4-hexen-2-ol is treated with PBr3. (R)-2-bromo-5-methyl-4- hexene is formed. When this compound is treated with sodium ethoxide in ethanol, alkene A is formed. Draw the structure of alkene A. Draw a mechanism for its formation. Use a Newman projection to explain the stereochemistry of alkene A.What alkene with the molecular formula C6H12, when treated with ozone and then dimethyl sulfide, gives the following product(s)?(b) Treating cyclohexene with HBr in the presence of acetic acid gives bromocyclohexane (85%) and cyclohexyl acetate (15%). Propose a mechanism for the formation of the latter product using curly arrows. Br оссH, CH,COH + HBr 85% 15%
- Draw the products formed when both cis- and trans-but-2-ene are treated with a peroxyacid followed by -OH (in H2O).Explain how these reactions illustrate that anti dihydroxylation is stereospecic.Compound A is an alkene that was treated with ozone (followed by DMS) to yield only (CH3CH2CH2)2C=O. Draw the major product that is expected when compound A is treated with a peroxy acid (RCO3H) followed by aqueous acid (H30*).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.