SN2 reaction
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| + | == S<sub>N</sub>2-Substitution of chloride and methanol == | ||
| + | <StructureSection load='' size='340' side='right' caption='' scene='54/542286/Side_view/2'> | ||
SN2 reaction is a basic reaction type in organic chemistry. The letter S<sub>N</sub> stand for nulceophilic Substitution, the number 2 stands for bimolecular. This means that both reactions partners are involved in the reaction rate determining step. It also exists an S<sub>N</sub>1 reaction; here, only one reaction partner is involved in this step. | SN2 reaction is a basic reaction type in organic chemistry. The letter S<sub>N</sub> stand for nulceophilic Substitution, the number 2 stands for bimolecular. This means that both reactions partners are involved in the reaction rate determining step. It also exists an S<sub>N</sub>1 reaction; here, only one reaction partner is involved in this step. | ||
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| - | + | Typically, alkanes with a substituent in primary position undergo S<sub>N</sub>2 reactions. In contrast to a S<sub>N</sub>1 reaction, no stable carbo cation can be formed. Therefore, another way will be taken. | |
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| - | Typically, alkanes with a substituent in primary position undergo S<sub>N</sub>2 reactions. In contrast to a S<sub>N</sub>1 reaction, no stable carbo cation can be formed. Therefore, another way will be taken. | + | |
The S<sub>N</sub>2 <jmol><jmolLink><script>anim mode once; frame range 1 10; delay 0.5; frame play</script><text>reaction starts</text></jmolLink></jmol> by establishing a so called intermediate state. This means that both educts come close to each other. By this, the bond of the leaving group is partly broken, and the bond to the new group is partly formed. The formation of this intermediate state is the rate determining step of the reaction. | The S<sub>N</sub>2 <jmol><jmolLink><script>anim mode once; frame range 1 10; delay 0.5; frame play</script><text>reaction starts</text></jmolLink></jmol> by establishing a so called intermediate state. This means that both educts come close to each other. By this, the bond of the leaving group is partly broken, and the bond to the new group is partly formed. The formation of this intermediate state is the rate determining step of the reaction. | ||
In the <jmol><jmolLink><script>anim mode once; frame range 11 20; delay 0.5; frame play</script><text>second step</text></jmolLink></jmol>, the bond of the leaving group is completely broken, and at the same time the bond to the new substituent is completely formed. | In the <jmol><jmolLink><script>anim mode once; frame range 11 20; delay 0.5; frame play</script><text>second step</text></jmolLink></jmol>, the bond of the leaving group is completely broken, and at the same time the bond to the new substituent is completely formed. | ||
| - | [[Image:reaction_scheme_sn2.jpg]] | + | [[Image:reaction_scheme_sn2.jpg|500px]] |
The S<sub>N</sub>2 reaction has a very interesting stereochemistry. | The S<sub>N</sub>2 reaction has a very interesting stereochemistry. | ||
inversion of the stereocenter... | inversion of the stereocenter... | ||
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<jmol> | <jmol> | ||
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<jmolButton><script>animation mode palindrome 0.5 0.2; anim on</script><text>Loop backwards and forward</text></jmolButton> | <jmolButton><script>animation mode palindrome 0.5 0.2; anim on</script><text>Loop backwards and forward</text></jmolButton> | ||
<jmolButton><script>if(_animating);anim off;else;frame play;endif</script><text>Toggle animation</text></jmolButton> | <jmolButton><script>if(_animating);anim off;else;frame play;endif</script><text>Toggle animation</text></jmolButton> | ||
| - | </jmol> | + | </jmol> |
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| - | {{Clear}} | ||
This demo was adapted from http://www.chemieunterricht-interaktiv.de/en/animations/sn2_substitution/sn2_substitution_3d.html by Dr. V. Pietzner, part of the ChiLe project | This demo was adapted from http://www.chemieunterricht-interaktiv.de/en/animations/sn2_substitution/sn2_substitution_3d.html by Dr. V. Pietzner, part of the ChiLe project | ||
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===See also=== | ===See also=== | ||
[[SN1_reaction|S<sub>N</sub>1 reaction: Substitution of Cl<sup>−</sup> and ''tert''-Butanol ]] | [[SN1_reaction|S<sub>N</sub>1 reaction: Substitution of Cl<sup>−</sup> and ''tert''-Butanol ]] | ||
| + | </StructureSection> | ||
| + | == References == | ||
| + | <references/> | ||
Revision as of 14:10, 8 October 2020
SN2-Substitution of chloride and methanol
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References
Proteopedia Page Contributors and Editors (what is this?)
Joel L. Sussman, Jaime Prilusky, Angel Herraez, Verena Pietzner
