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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?
- tertiary butyl alcohol
- isopropyl alcohol
- (CH3)2CCH2CH3 (correct)
- 2-methyl-2-butanol
Williamson's synthesis is used exclusively for preparing alcohols.
Williamson's synthesis is used exclusively for preparing alcohols.
False (B)
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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