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Questions and Answers
Which of the following is a product of the reaction involving (CH3)3CCH2OH and HCl?
Which of the following is a product of the reaction involving (CH3)3CCH2OH and HCl?
Williamson's synthesis is used exclusively for preparing alcohols.
Williamson's synthesis is used exclusively for preparing alcohols.
False
What is the purpose of oxymercuration-demercuration in organic synthesis?
What is the purpose of oxymercuration-demercuration in organic synthesis?
To convert alkenes into alcohols.
In Williamson's synthesis, an alkoxide ion reacts with a ______ to form an ether.
In Williamson's synthesis, an alkoxide ion reacts with a ______ to form an ether.
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Match the following alcohols with their corresponding synthesis method:
Match the following alcohols with their corresponding synthesis method:
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Study Notes
Williamson Synthesis Overview
- Named after Alexander Williamson; useful for creating ethers.
- Involves an alkoxide and a primary alkyl halide.
- Key feature: nucleophilic substitution reaction (SN2 mechanism).
- Commonly used to prepare symmetrical and unsymmetrical ethers.
Preparing Methyl Isopropyl Ether
- Method 1: React methyl iodide with sodium isopropoxide.
- Method 2: React isopropyl bromide with sodium methylate.
- Method choice: Methyl iodide generally offers better yields due to less steric hindrance in SN2 reactions.
Mechanism of Reaction (CH3)3CCH2OH with HCl
- Protonation occurs on the alcohol group, forming a better leaving group.
- Carbocation formation follows, leading to rearrangement.
- Alkyl halide (CH3)2CCH2CH3 is formed along with water as a byproduct.
Oxymercuration-Demercuration for Alcohol Synthesis
- Process: Involves marking the nucleophile addition to alkenes.
- For tert-Butyl alcohol: Starting alkene is 1-butene; undergoes mercuration followed by demercuration.
- For Isopropyl alcohol: Starting alkene is propylene; follow similar mercuration-demurcuration steps.
- For 2-Methyl-2-butanol: Starting alkene is methyl-2-butene; complete the mercuration-demurcuration process.
Williamson's Synthesis of 2-Methoxypropane
- Begin with sodium methoxide as the alkoxide.
- React with 2-bromopropane (primary halide).
- This results in the formation of 2-methoxypropane.
Examples of Compounds Prepared by Williamson's Synthesis
- Mainly prepares ethers.
- Example: Ethoxyethane (diethyl ether) can be synthesized using ethoxide with ethyl halide.
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Description
This quiz covers various chemistry problems based on TU 2055 and 2056. It includes questions on Williamson synthesis methods for preparing methyl isopropyl ether, reaction mechanisms, and synthesis of alcohols using oxymercuration. Test your understanding of organic chemistry concepts and reactions.
