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- CH3 CH3 Br- Br2 .CH3 CH2Cl2 CH3 H3C H3C Br Electrophilic addition of bromine, Brɔ, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl,. In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 CH3 CH3 CH3 H3C H3C :Br: :Br:Questão 10A certain hydrocarbon had the molecular formula C16H26 and contained two triple bonds. Ozonolysis resulted in CH3(CH2)4CO2H and HO2CCH2CH2CO2H as the only products. What is the reasonable structure for this hydrocarbon? Hexadec-6,10-dino undec-1,5-dino Hept-1,5-dino hex-1,5-dino nah4. What are the products obtained from the following elimination reaction? Indicate the major product. CH;CH2CCH3 H2O CI 5. a) Determine the major product that is formed when the alkyl halide reacts with a hydroxide ion in an elimination reaction. CH;CH,CH,CH,CCH3 Br b) For the major elimination product obtained in 5a), which stereoisomer (cis or trans) is obtained in greater yield? Draw the two isomers and provide the names of the compounds.
- Provide the structure(s) of the expected major organic product of the reaction shown. 1) Disiamylborane 2) H₂O₂, NaOH OI O II ||| O IV OV CH3CH₂C(CH3)2C=CH OH OH xx xo IVBicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide a mechanism for each step.5A In the following reactions, mixtures of alkenes and ethyl ethers are formed. Draw their structures. Explain which is or are likely to be the main product(s) in each reaction. In case of formation of two isomers of alkenes, explain which is formed in greater proportion CH3 ofi H3C- -Br CH3 EtOH
- OH 1. Hg(OAc)2, H2O 2. NABH4 CH3 .CH3 H2C H3C ČH3 CH3 Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H adds to the sp carbon with the most hydrogens to yield the most stable carbocation intermediate, which then adds water to give the product alcohol. Because a carbocation intermediate is formed, rearrangements can occur prior to the addition of water. To avoid the possibility of rearrangement and still give a Markovnikov alcohol, alkenes can instead be treated with mercury(II) acetate in aqueous THF and then subsequently reduced with sodium borohydride. This reaction proceeds through a cyclic mercurinium ion intermediate which cannot rearrange. Water adds to the cyclic intermediate at the most substituted carbon to give an organomercury alcohol. The reduction step with sodium borohydride is complex and involves radicals. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing…6) 25pts. Draw the structure of the major alkene product (or products) formed by treatment of each of the following haloalkanes with sodium ethoxide in ethanol. Assume the mechanism is E2 elimination. t-BuO K t-BUOH Br CH3 Eto Na F ETOH CH2CH3 CI H- Eto Na -CH2CH3 ELOH H- ČH3 Br Eto Na ELOH CH3 CI, H Eto Na CH2CH3 H3C H D ELOHH3C CH3 H3C NA C→XT Br Br₂ CH₂Cl₂ H3C Electrophilic addition of bromine, Br₂, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH₂Cl₂. CH3 Br In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br CH3 H3C CH3
- 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 BPredict (by name) the major product for the following reaction. The starting compound is byblo[4.4.0]dec-1-ene. Note the numbering and name the product.When the given reactions below are done once, which of the following reactions is used to prepare dihalogenated alkyl halides as major products? Select one: O Reaction of ethane with Cl₂ in the presence of light Reaction of ethene with HBr Reaction of ethyne with two moles of HCI Reaction of ethene with Br₂ in H₂O