Draw curved arrows to show the movement of electrons in this step of the mechanism.
Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H+ adds to the sp2 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.
Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H+ adds to the sp2 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.
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Draw curved arrows to show the movement of electrons in this step of the mechanism.
Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry
Acid-catalyzed addition of water to an alkene yields an alcohol
with Markovnikov regiochemistry. The electrophilic H+ adds to the
sp^2 carbon with the most hydrogens to yield the most stable
carbocation intermediate, which then adds water to give the product
alcohol. To avoid the possibility of rearrangement and still give a Markovnikov alcohol, alkenes can instead be treated with mercury(II) acetate in aqucous THF and then subsequently reduced with sodium borohydride. This reaction proceeds through a cyclic mercurinium ion intermediate which...
1. Hg(OAc)2, H20 2. NaBHA CH3 M HC CHE нас Acid-catalyzed addition of water to an...
1. Hg(OAc)2, H20 2. NaBHA CH3 M HC CHE нас 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...
CH3 CH3 1. Hg(OAC), H20 2. NaBH НО, І CH3 CH, Hoc H₃C/ Acid-catalyzed addition of...
CH3 CH3 1. Hg(OAC), H20 2. NaBH НО, І CH3 CH, Hoc H₃C/ 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...
2 problems 1. Hg(OAC)2, H20 2. NaBHg CH3 H3C H₃C Acid-catalyzed addition of water to an...
2
problems
1. Hg(OAC)2, H20 2. NaBHg CH3 H3C H₃C Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic add carbon with the most hydrogens to yield the most stable carbocation intermediate, which then adds water to give the produc 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...
(Review Topics 1. Hg(OAC)2, H20 2. NaBH, . H2O OH CHI CH3 H3C H3C Hoc Acid-catalyzed...
(Review Topics 1. Hg(OAC)2, H20 2. NaBH, . H2O OH CHI CH3 H3C H3C Hoc Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov repiochemistry. The electrophilic 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...
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Electrophilic addition of hypohalous acids to alkenes yields a 1,2-haloalcohol called a halohydrin. Halohydrin formation, however, does not result from the addition of HO-Br, for example. Instead the addition is done indirectly by reaction of the alkene with Br2 in the presence of water. The reaction also works with Cl2 to give chlorohydrins instead of bromohydrins. The reaction proceeds through a cyclic intermediate known as a bromonium ion. In the second step of the reaction, water is the nucleophile and reacts with the...
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Electrophilic addition of bromine, Br-, 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 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...
Draw curved arrows to show the movement of electrons in this step of the mechanism.
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 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...
Acid Catalyzed Hydration-treatment of alkenes with water in the presence of acid catalyst leads to the...
Acid Catalyzed Hydration-treatment of alkenes with water in the presence of acid catalyst leads to the formation of alcohols. H2SO4/H2O > 150°C Mechanism Major Product Acid catalyzed dehydration goes through a carbocation intermediate. This means that the Markovnikov product is obtained when carbocation rearrangements do not occur. The need for excessively high temperatures makes this reaction of limited use in laboratory synthesis. Oxymercuration - Oxymercuration involves the addition of Hg to the alkene using mercury (II) acetate Hg(OAc) followed by...
O- CHE Br CH2 H3C Hac Electrophilic addition of HBr toalkenes yields a bromoalkane. The reaction...
Electrophilic addition of HBr to alkenes yields a bromoalkane. The reaction begins with an attack on the hydrogen of the electrophilic HBr by the electrons of the double bond to give a carbocation. This step follows Markovnikov's rule with the electrophilic H atom adding to the sp2 carbon containing the most hydrogens, leading to the formation of the most stable carbocation (1° < 2° < 3°). If possible, a 1,2-shift of either a neighboring hydride or methyl group can occur...
1. Hg(OAc)2, H20 2. NaBHA CH3 M HC CHE нас 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...
CH3 CH3 1. Hg(OAC), H20 2. NaBH НО, І CH3 CH, Hoc H₃C/ 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...
2
problems
1. Hg(OAC)2, H20 2. NaBHg CH3 H3C H₃C Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic add carbon with the most hydrogens to yield the most stable carbocation intermediate, which then adds water to give the produc 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...
(Review Topics 1. Hg(OAC)2, H20 2. NaBH, . H2O OH CHI CH3 H3C H3C Hoc Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov repiochemistry. The electrophilic 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...
Acid Catalyzed Hydration-treatment of alkenes with water in the presence of acid catalyst leads to the formation of alcohols. H2SO4/H2O > 150°C Mechanism Major Product Acid catalyzed dehydration goes through a carbocation intermediate. This means that the Markovnikov product is obtained when carbocation rearrangements do not occur. The need for excessively high temperatures makes this reaction of limited use in laboratory synthesis. Oxymercuration - Oxymercuration involves the addition of Hg to the alkene using mercury (II) acetate Hg(OAc) followed by...
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