18. A routine addition of HBr through the double bond
of a vinylcyclopentane gave
A small amount of an unexpected product. Propose a mechanism
for
formation of this product and explain why reorganization
occurs.
Homework Answers
![CH3 HBr - Br (Hz Mechanism : 1. HBO H+ +55 H + 2. (2° Carbocation less stable ) [1, 2] bond shift Br (3° Cartocation more sta](http://img.homeworklib.com/questions/099e3960-7111-11ea-85d0-d1fb3f8b1fd1.png?x-oss-process=image/resize,w_560)
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18. A routine addition of HBr through the double bond
of a vinylcyclopentane gave
A small...
The addition of HBr to 1,3-butadiene in the presence of a catalytic amount of peroxides
The addition of HBr to 1,3-butadiene in the presence of a catalytic amount of peroxides gives the expected product from anti-Markovnikov addition of HBr to one of the double bonds (BrCH2CH2CH CHa) and another product as shown below. Propose mechanism that explains how this product could be formed via a free radical mechanism. (Note: An ionic mechanism for the addition of HBr is also a possible explanation for the formation of the product. This is not what I am looking for...
A. Double bonds that are connected by a single bond are said to be conjugated. For...
A. Double bonds that are connected by a single bond are said to be conjugated. For each molecule below, indicate how many conjugated double bonds are present in each molecule. HO OH bro HO B. One feature that distinguishes conjugated dienes from isolated dienes is that the C-C bond joining the two double bonds is unusually short. For each of the molecules in Part A, indicate which C-C single bond(s) might be shorter than expected. C. Some reactions of conjugated...
Electrophilic addition of HBr to alkenes yields a bromoalkane.
Electrophilic addition of HBr to alkenes yields a bromoalkane. The reaction begins with an attack on the hydrogen of the elect HBr by the π electrons of the double bond to give a carbocation. This step follows Markovnikov's rule with the electrophilic H 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...
Electrophilic addition of HBr to alkenes yields a bromoalkane.
Electrophilic addition of HBr to alkenes yields a bromoalkane. The reaction begins with an attack on the hydrogen of the electrophilic HBr by the n 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 prior to the...
Electrophilic addition of HBr to alkenes yields a bromoalkane
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...
Electrophilic addition of HBr to alkenes yields a bromoalkane.
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 prior...
Electrophilic addition of HBr to alkenes yields a bromoalkane
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 prior...
In many addition reactions we have to think about the regiochemical preference of how the two...
In many addition reactions we have to think about the regiochemical preference of how the two new groups will add across a double bond. Draw the major product of each transformation. HBr HBr ΒΡΟ For each transformation, which set of reagents would produce each product shown below in the highest yield? - In the box below, draw a curved-arrow reaction mechanism for the following reaction. Show all bond cleavage and formation steps. Your answer should be written in the box...
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...
a) There are several reagents that can be used to effect addition to a double bond,...
a) There are several reagents that can be used to effect
addition to a double bond, including: acid and water,
oxymercuration--demercuration reagents, and
hydroboration--oxidation reagents. Inspect the final product and
select all the reasons why oxymercuration--demercuration was chosen
to effect the following transformation instead of the other
reagents.
b) Complete the mechanism for the reaction by adding curved
arrows. The reagents chosen for the transformation are: 1)
Hg(OAc)2, THF, H2O and 2) NaBH4, OH
A. Double bonds that are connected by a single bond are said to be conjugated. For each molecule below, indicate how many conjugated double bonds are present in each molecule. HO OH bro HO B. One feature that distinguishes conjugated dienes from isolated dienes is that the C-C bond joining the two double bonds is unusually short. For each of the molecules in Part A, indicate which C-C single bond(s) might be shorter than expected. C. Some reactions of conjugated...
In many addition reactions we have to think about the regiochemical preference of how the two new groups will add across a double bond. Draw the major product of each transformation. HBr HBr ΒΡΟ For each transformation, which set of reagents would produce each product shown below in the highest yield? - In the box below, draw a curved-arrow reaction mechanism for the following reaction. Show all bond cleavage and formation steps. Your answer should be written in the box...
a) There are several reagents that can be used to effect
addition to a double bond, including: acid and water,
oxymercuration--demercuration reagents, and
hydroboration--oxidation reagents. Inspect the final product and
select all the reasons why oxymercuration--demercuration was chosen
to effect the following transformation instead of the other
reagents.
b) Complete the mechanism for the reaction by adding curved
arrows. The reagents chosen for the transformation are: 1)
Hg(OAc)2, THF, H2O and 2) NaBH4, OH
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