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Does vinyl chloride have greater electrophilic addition rate than ethene?
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Lisa Ford
Does vinyl chloride have greater electrophilic addition rate than ethene?
Ethene will have a greater rate of electrophilic addition than vinyl chloride. This is because ethene is more nucleophilic than vinyl chloride. The lesser nucleophilic nature is attributed to the electron withdrawing nature of chlorine atom.
Here chlorine can show both the +M and the -I effects. But the +M effect doesn't increase its nucleophilic nature much. This is because there is a large energy gap between the the bonding orbitals of carbon and chlorine which leads to an ineffective back bonding from chlorine to carbon. To confirm this let us refer to the bond lengths of $\ce{C-Cl}$ in vinyl chloride and chloroethane.
The $\ce{C-Cl}$ bond length in chloroethane is $\ce{1.789Å} $, whereas as in vinyl chloride it is just $\ce{1.726Å}$
From this data we can conclude that the back bonding is not much significant. But chlorine can exhibit significant -I effect and this is attributed to its high electronegativity. (According to the Pauling scale, the electronegativities of $\ce{C}$ and $\ce{Cl}$ are $2.55$ and $3.16$ respectively.) As the -I effect is dominating the +M effect, chlorine atom acts as an electron withdrawing group and thereby it decreases the electron density making it less nucleophilic.
The effective back bonding can be observed in the case of $\ce{BF3}$. The $\ce{B-F}$ bond lengths in $\ce{BF3}$ and $\ce{BF4-}$ are nearly $\ce{1.31Å}$ and $\ce{1.40Å}$. Here we can observe a significant change in bond length.
Ethene will have a greater rate of electrophilic addition than vinyl chloride. This is because ethene is more nucleophilic than vinyl chloride. The lesser nucleophilic nature is attributed to the electron withdrawing nature of chlorine atom.
Here chlorine can show both the +M and the -I effects. But the +M effect doesn't increase its nucleophilic nature much. This is because there is a large energy gap between the the bonding orbitals of carbon and chlorine which leads to an ineffective back bonding from chlorine to carbon. To confirm this let us refer to the bond lengths of $\ce{C-Cl}$ in vinyl chloride and chloroethane.
The $\ce{C-Cl}$ bond length in chloroethane is $\ce{1.789Å} $, whereas as in vinyl chloride it is just $\ce{1.726Å}$
From this data we can conclude that the back bonding is not much significant. But chlorine can exhibit significant -I effect and this is attributed to its high electronegativity. (According to the Pauling scale, the electronegativities of $\ce{C}$ and $\ce{Cl}$ are $2.55$ and $3.16$ respectively.) As the -I effect is dominating the +M effect, chlorine atom acts as an electron withdrawing group and thereby it decreases the electron density making it less nucleophilic.
The effective back bonding can be observed in the case of $\ce{BF3}$. The $\ce{B-F}$ bond lengths in $\ce{BF3}$ and $\ce{BF4-}$ are nearly $\ce{1.31Å}$ and $\ce{1.40Å}$. Here we can observe a significant change in bond length.
Ethene will have a greater rate of electrophilic addition than vinyl chloride. This is because ethene is more nucleophilic than vinyl chloride. The lesser nucleophilic nature is attributed to the electron withdrawing nature of chlorine atom.
Here chlorine can show both the +M and the -I effects. But the +M effect doesn't increase its nucleophilic nature much. This is because there is a large energy gap between the the bonding orbitals of carbon and chlorine which leads to an ineffective back bonding from chlorine to carbon. To confirm this let us refer to the bond lengths of $\ce{C-Cl}$ in vinyl chloride and chloroethane.
From this data we can conclude that the back bonding is not much significant. But chlorine can exhibit significant -I effect and this is attributed to its high electronegativity. (According to the Pauling scale, the electronegativities of $\ce{C}$ and $\ce{Cl}$ are $2.55$ and $3.16$ respectively.) As the -I effect is dominating the +M effect, chlorine atom acts as an electron withdrawing group and thereby it decreases the electron density making it less nucleophilic.
The effective back bonding can be observed in the case of $\ce{BF3}$. The $\ce{B-F}$ bond lengths in $\ce{BF3}$ and $\ce{BF4-}$ are nearly $\ce{1.31Å}$ and $\ce{1.40Å}$. Here we can observe a significant change in bond length.
Ethene will have a greater rate of electrophilic addition than vinyl chloride. This is because ethene is more nucleophilic than vinyl chloride. The lesser nucleophilic nature is attributed to the electron withdrawing nature of chlorine atom.
Here chlorine can show both the +M and the -I effects. But the +M effect doesn't increase its nucleophilic nature much. This is because there is a large energy gap between the the bonding orbitals of carbon and chlorine which leads to an ineffective back bonding from chlorine to carbon. To confirm this let us refer to the bond lengths of $\ce{C-Cl}$ in vinyl chloride and chloroethane.
From this data we can conclude that the back bonding is not much significant. But chlorine can exhibit significant -I effect and this is attributed to its high electronegativity. (According to the Pauling scale, the electronegativities of $\ce{C}$ and $\ce{Cl}$ are $2.55$ and $3.16$ respectively.) As the -I effect is dominating the +M effect, chlorine atom acts as an electron withdrawing group and thereby it decreases the electron density making it less nucleophilic.
The effective back bonding can be observed in the case of $\ce{BF3}$. The $\ce{B-F}$ bond lengths in $\ce{BF3}$ and $\ce{BF4-}$ are nearly $\ce{1.31Å}$ and $\ce{1.40Å}$. Here we can observe a significant change in bond length.
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