. 1-methylcyclopentanol reacts with HBr to give the corresponding alkyl bromide via a carbocation intermediate. Draw the carbocation intermediate. Is this a primary, secondary or tertiary carbocation?
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- The acid HBr gives H+ which protonates the alcohol -OH to +OH2 .
- This then leaves as a water molecule, leaving behind a carbocation.
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- 2. The following carbocation is generated as an intermediate in the addition of H-Br to an alkene. Draw the structure of all possible alkenes that could have formed this intermediate.The pictured reaction shows an alkyl bromide being converted into an alkene. Choose all reagents that would produce the pictured alkene as the major product. A) NaOH/H2O B) H2O C) tBuOK/tBuOH D) EtONa/EtOHWhat about the second step in the electrophilic addition of HCl to an alkene-the reaction of chloride ion with the carbocation intermediate? Is this step exergonic or endergonic? Does the transition state for this second step resemble the reactant (carbocation) or the product (alkyl chloride)? Make a rough diagram of what the transition state may look like?
- draw the two possible carbocations that can form when this alkene reacts with a strong acid (such as HBr or H3O+). of the two structures you drew, circle the more stable carbocationH3C 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 CH3Suppose the alkene in the drawing area below is put in strong acid solution, for example a solution of HBr. Highlight each carbon that might become protonated to form a carbocation intermediate. (The carbocation intermediate might then react with something else to form a final product.) سعد
- 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:Alcohols undergo an oxidation reaction to yield carbonyl compounds on treatment with CrO3. For example, 2-tert-butylcyclohexanol gives 2-tert-butylcyclohexanone. If axial OH groups are generally more reactive than their equatorial isomers, which do you think reacts faster, the cis isomer of 2-tert-butylcyclohexanol or the trans isomer? Explain.N,N-diethyl-m-toluamide (DEET) is the active ingredient in many insect repellent preparations. Following is one of the steps in its synthesis. In the box below draw the structure of the product of this reaction. H3C MgBr 1. CO2 2. H3O+ product • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Draw the Grignard reagent as a covalent magnesium bromide. 90-87 0 + 11 ? n [
- Acid-catalyzed dehydration of 3,3-dimethyl-2-butanol gives three alkenes: 2,3-dimethyl-2-butene, 3,3-dimethyl- 1-butene, and 2,3-dimethyl-1-butene. Draw the structure of the carbocation intermediate leading to the formation of 2,3-dimethyl-2-butene. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • If more than one structure fits the description, draw them all. • Separate structures with + signs from the drop-down menu. / H₂C CH₂ CH3 CH3 ChemDoodleⓇ On []Acid-catalyzed dehydration of 3,3-dimethyl-2-butanol gives three alkenes: 2,3-dimethyl-2-butene, 3,3-dimethyl-1-butene, and 2,3-dimethyl-1- butene. Draw the structure of the carbocation intermediate leading to the formation of 2,3-dimethyl-2-butene. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. If more than one structure fits the description, draw them all. Separate structures with + signs from the drop-down menu. C P opy aste ChemDoodle >1. Reaction of 2,3-dimethyl-1-butene with HBr leads to an alkyl bromide, C6H13Br. On treatment of this alkyl halide with KOH in methanol, elimination of HBr occurs and a hydrocarbon that is isometric with the starting alkene is formed. What is the structure of this hydrocarbon and how do you think it is formed from an alkyl bromide? 2. 1-Octen-3-ol is a potent mosquito attractant commonly used in mosquito traps. A number of reactions, including hydrogenation, will transform 1-Octen-3-ol into a less effective molecule. Write a complete reaction equation for the hydrogenation of this alkenol.