CCHH20, H2SO4H9SO4CH3Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikovregiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also calledan enol. The enol immediately rearranges to a more stable ketone via tautomerization.Draw curved arrows to show the movement of electrons in this step of the mechanism.Arrow-pushing InstructionsHjö:-CH3-CH3H3O*

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Answered: c=CH H20, H2SO4 H9SO4 `CH3 Alkynes do…

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.44P

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Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions -X티 Hö: H-O -CH3 -CH3 H30*
Two substitution products result from the reaction between 3-chloro-3-methyl-1- butene with sodium acetate (CH3COO – Na +) in acetic acid under SN1. Identify the products.
C=CH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H-OH HO: Hjö: C=CH c=CH Hö Hg Hg
Like other electrophiles, carbocations add to alkenes to form new carbocations, which can then undergo substitution or elimination reactions depending on the reaction conditions. With this in mind, consider the following reactions of nerol, a natural product isolated from lemon grass and other plant sources. Treatment of nerol with TsOH forms α-terpineol as the major product, whereas treatment of nerol with chlorosulfonic acid, HSO3Cl, forms a constitutional isomer, α-cyclogeraniol. Write stepwise mechanisms for both processes. Each mechanism involves the addition of an electrophile—a carbocation—to a double bond.
Like other electrophiles, carbocations add to alkenes to form new carbocations, which can then undergo substitution or elimination reactions depending on the reaction conditions. With this in mind, consider the following reactions of nerol, a natural product isolated from lemon grass and other plant sources. Treatment of nerol with TsOH forms α-terpineol as the major product, whereas treatment of nerol with chlorosulfonic acid, HSO3Cl, forms a constitutional isomer, αcyclogeraniol. Write stepwise mechanisms for both processes. Each mechanism involves the addition of an electrophile— a carbocation—to a double bond.
You are required to synthesize 2-bromopentane from the reaction between an alkene with HBr. Which alkene, 1-pentene or 2-pentene, should you react with HBr in order to get 2-bromopentane? Give an explanation.
(1) Predict the outcome of the addition of HBr to (a) trans-2-pentene, (b) 2-methyl-2-butene, and (c) 4-methylcyclohexene. How many isomers can be formed in each case? (2) Addition of HBr to 3,3-dimethyl-1-butene gives a mixture of two isomeric alkyl bromide products. Draw structures for the two products, and give a mechanistic explanation for their formation.
Draw the structures of two alkenes that would react to form the haloalkane below upon addition of HBr. Your alkenes should be different regioisomers that yield the haloalkane as the major product without requiring rearrangement to occur.
Ethane reacts with chlorine (Cl2) in the presence of ultra-violet (UV) light, to produce 1-chloropropane (CH3CH2Cl) and hydrogen bromide (HCl). As shown in the equation below.CH3CH3+ Cl2→ CH3CH2Cl+ HClDescribe the reaction mechanism of the reaction between ethane and chlorine to produce 1-chloroethane. The description should be detailed and must include the type of bond fission that takes place. You may sketch and insert suitable diagrams to aid your description if you wish.
An alkene having the molecular formula C5H10 is treated sequentially with ozone (O3) and zinc/acetic acid to give the product/s shown. H3C O CH3CHCH + H. Draw a structural formula for the alkene. You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. In cases where there is more than one answer, just draw one. P opy aste [* Previous Next
2-chloropropane is a major product of the reaction of chlorine with propane under ultraviolet light. Write the mechanism for this reaction including the initiation step and the two propagation steps.
Na, NH3 H3C-C=C-CH3 CH3 H3C° Alkynes are reduced to trans alkenes by a process called dissolving metal reduction. The reaction uses sodium or lithium metal as the reducing agent and liquid ammonia as the solvent. The method is specific in the formation of trans alkenes from alkynes. The method involves two successive transfers of single electrons from the alkali metal to the triple bond, with abstraction of protons from the ammonia solvent. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions .CH3 H-NH2 CH3 :NH2 H3C H3C

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