3-Chlorobutane, 4-chlorobutane, allyl chloride, 2-chloro-2-methylpropane, 1-chloro-2-methylpropane, 2-bromobutane
a) Which alkyl halides were the most reactive under SN2 conditions? Which were the least reactive? Explain the order of reactivity under SN2 conditions by considering alkyl halide structure, nature of the leaving group, temperature, solvent, etc. Does the experimentally determined order fit what you predicted? Account for any anomalous observations.
b) Which alkyl halides were the most reactive under SN1 conditions? Which were the least reactive? Explain the order of reactivity under SN1 conditions by considering alkyl halide structure, nature of the leaving group, temperature, solvent, etc. Does the experimentally determined order fit what you predicted? Account for any anomalous observations.
Post Lab Questions
(1) Two of your six alkyl halides cannot react via an SN1 mechanism. Which are they? Why are they unreactive under SN1 conditions?
(2) One of your six alkyl halides reacts rapidly via both SN1 and SN2 mechanisms. Which is it, and why is it reactive under both mechanisms?
(3) One of your six alkyl halides is essentially unreactive via either SN1 or SN2 mechanisms. Which is it, and why is it unreactive?
(4) Explain why we used acetone as solvent for the SN2 reactions, and ethanol as solvent for the SN1 reactions.
(5) Allyl chloride is carcinogenic, as you determined in the prelab. Carcinogenic alkylating agents react with DNA bases such as cytosine (below), causing a change in the base structure, DNA mismatches and mutations which can lead to cancer. Draw a plausible reaction of allyl chloride with cytosine, and based on your results from this experiment, explain why allyl chloride is carcinogenic but 2- chlorobutane is not.
3-Chlorobutane, 4-chlorobutane, allyl chloride, 2-chloro-2-methylpropane, 1-chloro-2-methylpropane, 2-bromobutane
a) Which alkyl halides were the most reactive under SN2 conditions? Which were the least reactive? Explain the order of reactivity under SN2 conditions by considering alkyl halide structure, nature of the leaving group, temperature, solvent, etc. Does the experimentally determined order fit what you predicted? Account for any anomalous observations.
b) Which alkyl halides were the most reactive under SN1 conditions? Which were the least reactive? Explain the order of reactivity under SN1 conditions by considering alkyl halide structure, nature of the leaving group, temperature, solvent, etc. Does the experimentally determined order fit what you predicted? Account for any anomalous observations.
Post Lab Questions
(1) Two of your six alkyl halides cannot react via an SN1 mechanism. Which are they? Why are they unreactive under SN1 conditions?
(2) One of your six alkyl halides reacts rapidly via both SN1 and SN2 mechanisms. Which is it, and why is it reactive under both mechanisms?
(3) One of your six alkyl halides is essentially unreactive via either SN1 or SN2 mechanisms. Which is it, and why is it unreactive?
(4) Explain why we used acetone as solvent for the SN2 reactions, and ethanol as solvent for the SN1 reactions.
(5) Allyl chloride is carcinogenic, as you determined in the prelab. Carcinogenic alkylating agents react with DNA bases such as cytosine (below), causing a change in the base structure, DNA mismatches and mutations which can lead to cancer. Draw a plausible reaction of allyl chloride with cytosine, and based on your results from this experiment, explain why allyl chloride is carcinogenic but 2- chlorobutane is not.
Related textbook solutions
Basic Chemistry
Principles of Chemistry Molecular Approach
Principles of Chemistry Molecular Approach
Chemistry: Structure and Properties
Chemistry: A Molecular Approach
Chemistry: A Molecular Approach
Principles of Chemistry: A Molecular Approach
