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- Oct 24, 2005
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Here ya go! I figured I would take the time to post this. (thanks to Mstoothlady2012 & ScienceAide)
SN1 -- Prefer in order: 3'>2'> 1' and will not react with methyls.
Prefers good leaving groups in order:
I- > Br- > Cl- > F- > OH- > OR- > NH2 -
The strength of the nucleophile does not matter, because it is a two-step reaction and the first step is the rate limiting step. The first step is the spontaneous dissociation of the leaving group. (this is why it prefers a highly substituted C)
Prefers Polar Protic Solvents: ex. Water, Alcohol, Carboxylic Acids, Ammonia
2 step mechanism, rate kinetics dependent on only the reactant.
SN2 -- Prefers in order: methyl > 1' > 2' and will not react with tertiary.
Prefers good leaving groups in order:
I- > Br- > Cl- > F- > OH- > OR- > NH2 -
Prefers a strong nucleophile, because it is required to 'force' the leaving group off of the carbon chain.
Nucleophilic Strength: OR- > OH- > RCOO- > ROH > H20
Prefers Polar Aprotic solvents: ex. Aldehyde, Ketone, DMSO, acetone, DMF, acetonitrile, and HMPA
single step mechanism, and rate kinetics dependent on both reactant and nucleophile concentration. (The higher the concentration of each, the greater chance of a collision between the two)
E1- Prefers in order: 3' > 2' (will probably not react with primary or methyl groups)
( For a secondar reaction, it will require a strong base)
Likes good leaving groups, but less important for E1 than SN1
The nucleophilic strength is not significant for the same reason as SN1.
Prefers polar protic solvents: Water, alcohol, carboxylic acids, ammonia
Mechanism and kinetics follow same trend as SN1
E2- Prefers in order: Methyl > 1' > 2' > 3' (Tertiary is very unlikely, but requires strong base)
Likes good leaving groups.
I- > Br- > Cl- > F- > OH- > OR- > NH2 -
Prefers Polar Aprotic Solvents: DMSO, aldehyde, ketone, acetone, DMF, acetonitrile, and HMPA
Single step reaction, that relies on Anitperiplanar configuration so that there is no hindrance in the large electron shuffle that takes place in that single step.
If anyone would like to add to the list of Solvents, bases, nucleophiles, etc, please reply to this thread. Good luck
SN1 -- Prefer in order: 3'>2'> 1' and will not react with methyls.
Prefers good leaving groups in order:
I- > Br- > Cl- > F- > OH- > OR- > NH2 -
The strength of the nucleophile does not matter, because it is a two-step reaction and the first step is the rate limiting step. The first step is the spontaneous dissociation of the leaving group. (this is why it prefers a highly substituted C)
Prefers Polar Protic Solvents: ex. Water, Alcohol, Carboxylic Acids, Ammonia
2 step mechanism, rate kinetics dependent on only the reactant.
SN2 -- Prefers in order: methyl > 1' > 2' and will not react with tertiary.
Prefers good leaving groups in order:
I- > Br- > Cl- > F- > OH- > OR- > NH2 -
Prefers a strong nucleophile, because it is required to 'force' the leaving group off of the carbon chain.
Nucleophilic Strength: OR- > OH- > RCOO- > ROH > H20
Prefers Polar Aprotic solvents: ex. Aldehyde, Ketone, DMSO, acetone, DMF, acetonitrile, and HMPA
single step mechanism, and rate kinetics dependent on both reactant and nucleophile concentration. (The higher the concentration of each, the greater chance of a collision between the two)
E1- Prefers in order: 3' > 2' (will probably not react with primary or methyl groups)
( For a secondar reaction, it will require a strong base)
Likes good leaving groups, but less important for E1 than SN1
The nucleophilic strength is not significant for the same reason as SN1.
Prefers polar protic solvents: Water, alcohol, carboxylic acids, ammonia
Mechanism and kinetics follow same trend as SN1
E2- Prefers in order: Methyl > 1' > 2' > 3' (Tertiary is very unlikely, but requires strong base)
Likes good leaving groups.
I- > Br- > Cl- > F- > OH- > OR- > NH2 -
Prefers Polar Aprotic Solvents: DMSO, aldehyde, ketone, acetone, DMF, acetonitrile, and HMPA
Single step reaction, that relies on Anitperiplanar configuration so that there is no hindrance in the large electron shuffle that takes place in that single step.
If anyone would like to add to the list of Solvents, bases, nucleophiles, etc, please reply to this thread. Good luck
