Experiment 8: SN2 Reaction – Flashcards
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To see what and how factors (such as steric hindrance, nucleophilicity, and leaving groups) affect an SN2 reaction's rate
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Aim?
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When another atom replaces the halide ion that leaves
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Substitution
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When the halide ion leaves with another atom or ion (H+ usually)
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Elimination
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A nucleophile replaces a leaving group from a carbon atom, using its lone pair of electrons to form a new bond to the carbon atom
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Nucleophilic substitution
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Takes place in more than one step
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SN1
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Takes place in a single step, involves attacking the nucleophile and getting rid of the leaving group at the same time
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SN2
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A quaternary ammonium salt
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What does the reaction of a tertiary amine with an organic halide produce?
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A group 7 gas
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What is a halide?
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Strength of the nucleophile, the solvent, steric effects, and leaving groups
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Factors that affect SN2 reactions
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Any component that has a negative charge is stronger than one that doesn't
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How does the strength of the nucleophile effect SN2?
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Polar protic solvents slow down the substitution with their - nucleophiles. Polar Aprotic solvents speed up the substitution with their polar bonds. Non polar solvents won't dissolve nucleophiles
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How does the solvent effect SN2?
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When the nucleophile closely approaches the substrate, there can be adverse effects depending on the compound's structure
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How do steric effects affect SN2?
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Depends on electronegativity, stability, and polarizability of leaving group
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How do leaving groups effect SN2?
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Vacuum filtration
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What procedures were used here?
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Steric hindrance on the rate of the SN2, the nucleophilicity of the amine, and the nature of the leaving group
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What did this experiment evaluate the effects of?
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Triethylamine, tripropylamine, ethyldiisopropylamine
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What amines were tested?
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Iodoethane, 1-bromopropane, 2-bromopropane
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What alkyl halides were tested?
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It should turn cloudy and form a quaternary salt
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What should happen when acetone/diethyl ether/pentane, iodomethane, and amines are combined?
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When the amine's structure has considerably less branches
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When does steric hindrance have less of an effect on the reaction rate?
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By periodic table trends, whichever is bigger in atomic size has ^ nucleophilicity
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When nucleophiles all have the same charge, how is nucleophilicity determined?
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Faster rate
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Bigger atomic size =
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Fastest rate
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Lowest steric hindrance =
