The Sn1 Mechanism: Synthesis of tert-Butyl Chloride Flashcards
What are the safety hazards of this experiment?
fumes and skin burns
Why is it important that the HCL is concentrated?
The increased concentration of HCl will increase the rate in which it deprotonates the tert butyl alcohol
Why is it important that the flask containing the HCl is cooled?
substitution is favored over elimination at colder temperatures
Why is it important that we gently swirl the solution?
to prevent liquid-liquid emulsions
Why do we need to release gas pressure?
venting allows for pressure within the sep funnel to decrease
Why do we have to let the sep funnel sit for 20 minutes?
to give enough time for the aqueous and organic layer to separate
Why do we need to uncap the separatory funnel after draining the aqueous layer?
this will allow the funnel to flow freely past the stopcock without creating air bubbles
What is the purpose of the sodium bicarbonate solution in the experiment?
Sodium bicarb is a week base and will deprotonate the remaining HCl, allowing it to move into the aqueous layer to be discarded
What is the purpose of washing the product with 10mL of water after the washing of sodium bicarb
to ensure that all of the sodium bicarb has been flushed from the organic layer
Why do we wash the product with 20mL of sodium chloride?
to pull any remaining water away from the organic layer
What is the purpose of the anhydrous sodium sulfate?
the anhydrous sodium sulfate reacts with any leftover water in the organic layer and forms sodium sulfate hydrate, a solid that may be filtered out
What is the limiting reagent of this reaction?
tert-butyl alcohol
what kind of compounds in a reaction are most likely to proceed via the Sn1 mechanism?
tertiary and some secondary alcohols in the presence of strong acids
what type of solvents are best for Sn1 reactions?
polar protic - hydrogen (H) directly connected to an electrophilic molecule like O, F, and N
What is the nucleophile in this reactrion?
chloride ion
