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How many of the following ethers CANNOT ...

How many of the following ethers CANNOT be prepared by Williamson's synthesis?
`CH_(3)OCH_(2)CH_(3),C_(6)H_(5)OCH_(3), (C_(6)H_(5))_2O, (CH_(3))_(3)COCH_(3),(C_(2)H_(5))_2O, (CH_(3))_(3)C-O- C(CH_3)_(3)`

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To determine how many of the given ethers cannot be prepared by Williamson's synthesis, we need to analyze each ether based on the principles of the synthesis. ### Step-by-Step Solution: 1. **Understanding Williamson's Synthesis**: - Williamson's synthesis involves the reaction of an alkoxide ion (RO⁻) with an alkyl halide (R'X) to form an ether (ROR'). - The reaction proceeds via an SN2 mechanism, which is effective for primary alkyl halides and some secondary ones, but not for tertiary alkyl halides due to steric hindrance. 2. **List of Ethers**: - **Ether 1**: CH₃OCH₂CH₃ (Ethyl methyl ether) - **Ether 2**: C₆H₅OCH₃ (Methyl phenyl ether) - **Ether 3**: (C₆H₅)₂O (Diphenyl ether) - **Ether 4**: (CH₃)₃COCH₃ (Tert-butyl methyl ether) - **Ether 5**: (C₂H₅)₂O (Diethyl ether) - **Ether 6**: (CH₃)₃C-O-C(CH₃)₃ (Tert-butyl ether) 3. **Analyzing Each Ether**: - **Ether 1 (CH₃OCH₂CH₃)**: - Alkoxide: CH₃O⁻ (from CH₃OH) - Alkyl halide: CH₃CH₂Cl (primary) - **Possible via Williamson's synthesis**. - **Ether 2 (C₆H₅OCH₃)**: - Alkoxide: C₆H₅O⁻ (from C₆H₅OH) - Alkyl halide: CH₃Cl (primary) - **Possible via Williamson's synthesis**. - **Ether 3 ((C₆H₅)₂O)**: - Alkoxide: C₆H₅O⁻ (from C₆H₅OH) - Alkyl halide: C₆H₅Cl (primary) - **Possible via Williamson's synthesis**. - **Ether 4 ((CH₃)₃COCH₃)**: - Alkoxide: (CH₃)₃CO⁻ (from (CH₃)₃COH) - Alkyl halide: CH₃Cl (primary) - **Not possible due to steric hindrance (tertiary alkoxide)**. - **Ether 5 ((C₂H₅)₂O)**: - Alkoxide: C₂H₅O⁻ (from C₂H₅OH) - Alkyl halide: C₂H₅Br (primary) - **Possible via Williamson's synthesis**. - **Ether 6 ((CH₃)₃C-O-C(CH₃)₃)**: - Alkoxide: (CH₃)₃CO⁻ (from (CH₃)₃COH) - Alkyl halide: (CH₃)₃CCl (tertiary) - **Not possible due to steric hindrance (tertiary alkyl halide)**. 4. **Conclusion**: - The ethers that cannot be prepared by Williamson's synthesis are: - (CH₃)₃COCH₃ (Ether 4) - (CH₃)₃C-O-C(CH₃)₃ (Ether 6) - Therefore, **2 ethers cannot be prepared by Williamson's synthesis**. ### Final Answer: **2 ethers cannot be prepared by Williamson's synthesis.**
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