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Naaphthalene will not participate in Diels Alder reaction, why?
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Nahum Germanen Godfrey
Naaphthalene will not participate in Diels Alder reaction, why?
Unlike the other person who answered, I can make it simple: A Diels-Alder reaction makes cyclic compounds (compounds that form a ring) by reacting two molecules together.
To complicate things a little: there is a diene (a carbon-containing compound with an alternating double-single-double bond pattern), and a dienophile (something with a double bond). All of the original double bonds are broken, new single bonds are formed between the diene and the dienophile, and a new double bond is formed between the original double bonds of the diene.
Unlike the other person who answered, I can make it simple: A Diels-Alder reaction makes cyclic compounds (compounds that form a ring) by reacting two molecules together.
To complicate things a little: there is a diene (a carbon-containing compound with an alternating double-single-double bond pattern), and a dienophile (something with a double bond). All of the original double bonds are broken, new single bonds are formed between the diene and the dienophile, and a new double bond is formed between the original double bonds of the diene.
There are two ways to look at this which are effectively equivalent. We could say that, because naphthalene is aromatic, it is a conjugated system and not really an alkene or diene. Therefore, there is no easy overlap of orbitals with the other component. Alternatively, we could say that the activation energy for a Diels-Alder reaction with naphthalene is prohibitively high because it dearomatise the system. However, this is not the end of the story. David Sarlah has shown that you can carry out [4+2] reactions with aromatic compounds and very strong dienophiles, if you shine light on the reaction to form a charge-transfer complex.
There are two ways to look at this which are effectively equivalent. We could say that, because naphthalene is aromatic, it is a conjugated system and not really an alkene or diene. Therefore, there is no easy overlap of orbitals with the other component. Alternatively, we could say that the activation energy for a Diels-Alder reaction with naphthalene is prohibitively high because it dearomatise the system. However, this is not the end of the story. David Sarlah has shown that you can carry out [4+2] reactions with aromatic compounds and very strong dienophiles, if you shine light on the reaction to form a charge-transfer complex.
Unlike the other person who answered, I can make it simple: A Diels-Alder reaction makes cyclic compounds (compounds that form a ring) by reacting two molecules together.
To complicate things a little: there is a diene (a carbon-containing compound with an alternating double-single-double bond pattern), and a dienophile (something with a double bond). All of the original double bonds are broken, new single bonds are formed between the diene and the dienophile, and a new double bond is formed between the original double bonds of the diene.
Unlike the other person who answered, I can make it simple: A Diels-Alder reaction makes cyclic compounds (compounds that form a ring) by reacting two molecules together.
To complicate things a little: there is a diene (a carbon-containing compound with an alternating double-single-double bond pattern), and a dienophile (something with a double bond). All of the original double bonds are broken, new single bonds are formed between the diene and the dienophile, and a new double bond is formed between the original double bonds of the diene.
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There are two ways to look at this which are effectively equivalent. We could say that, because naphthalene is aromatic, it is a conjugated system and not really an alkene or diene. Therefore, there is no easy overlap of orbitals with the other component. Alternatively, we could say that the activation energy for a Diels-Alder reaction with naphthalene is prohibitively high because it dearomatise the system. However, this is not the end of the story. David Sarlah has shown that you can carry out [4+2] reactions with aromatic compounds and very strong dienophiles, if you shine light on the reaction to form a charge-transfer complex.
There are two ways to look at this which are effectively equivalent. We could say that, because naphthalene is aromatic, it is a conjugated system and not really an alkene or diene. Therefore, there is no easy overlap of orbitals with the other component. Alternatively, we could say that the activation energy for a Diels-Alder reaction with naphthalene is prohibitively high because it dearomatise the system. However, this is not the end of the story. David Sarlah has shown that you can carry out [4+2] reactions with aromatic compounds and very strong dienophiles, if you shine light on the reaction to form a charge-transfer complex.
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