Exam (elaborations)
Organic Chemistry Lab I (CHEM 237) Experiment 10: Phase Transfer Catalysis 100% Solved
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Organic Chemistry Lab I (CHEM 237) Experiment 10: Phase Transfer Catalysis 100% Solved
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Organic Chemistry Lab I (CHEM 237) Experiment 10:Phase Transfer Catalysis 100% Solved
In the reaction to produce allyl 2-naphthyl ether, 2-naphthol is first reacted with aqueous sodium
hydroxide to make sodium 2-naphtholate, which then goes on to react with allyl bromide and
benzyltributylammonium chloride phase transfer catalyst, with dichloromethane as a solvent. Note:
the boxes in the diagram represent the layers inside the reaction flask part-way to completion. Place
the labels in the appropriate box. (If a molecule has significant solubility in both layers, it may be used
more than once). - ✔✔
A Williamson ether synthesis between 2-naphthol and allyl bromide is performed in the presence of a phase
transfer catalyst and strong base in dichloromethane solution. The reaction mix contains: unreacted allyl
bromide, unreacted 2-naphthol, benzyltributylammonium chloride, allyl naphthyl ether, and
dichloromethane. The reaction mix is passed through a silica gel mini column. Drag and drop the
components of the mixture that elute from the column into the blue box next to the sample vial. - ✔✔
A Williamson ether synthesis is shown below. 2-naphthol in the presence of sodium hydroxide
undergoes a deprotonation to give the alkoxide shown below. Benzyl bromide is then added and
undergoes a nucleophilic substitution by SN2 mechanism. Add curved arrows to demonstrate the
SN2 substitution described. - ✔✔
Sodium hydroxide can cause severe damage to skin and eyes. - ✔✔True
Lachrymators like allyl bromide are specifically dangerous because of their explosion hazard. - ✔✔False
The primary risk associated with dichloromethane is its flammability. - ✔✔False
Unused allyl bromide can be disposed of in the aqueous waste. - ✔✔False
Gloves and goggles are not required when handling sodium hydroxide. - ✔✔False
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