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13 Dec 2019

Decide the mechanism by which the following alkyl halides will be converted to alcohols by the substitution of the nucleophile, OH-. (SN1, SN2, or mor info needed) R-X + OH- ? R-OH + X-

1-bromo-1-methylcyclohexane
1-bromo-2,3-dimethylbutane
3-chloro-2,2-dimethylbutane
4-iodo-3-ethylhexane

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Jarrod Robel
Jarrod RobelLv2
17 Dec 2019

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Related questions

How many of the following responses are true?

1. SN2 leads to a racemization of sterechemistry due to the planar carbocation intermediate
2. A primary alkyl halide will tend to react through an SN2 mechanism because there is little hindrance to backside attack and a primary carbocation is not very stable
3. 1-bromopentane will undergo substitution through an SN1 mechanism
4. If R-3-bromo-3-methylhexane is allowed to react with OH- the product will be a 50%/50% mixture of R-3-methyl-3-hexanol and S-3-methyl-3-hexanol
5. SN1 leads to a racemization of sterechemistry due to the nucleophile attacking from the backside and the leaving group leaving



I'm confused on this problem

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.

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