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4. Which ONE of the following ethers cannot be prepared by a Williamson ether synthesis?

A. dimethyl ether
B. isopropyl ethyl ether
C. 2-ethoxybutane
D. methoxybenzene (methyl phenyl ether)
E. tert-butyl phenyl ether (t-butoxybenzene)

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Final answer:

The ether that cannot be prepared by a Williamson ether synthesis is tert-butyl phenyl ether.


Explanation:

The ether that cannot be prepared by a Williamson ether synthesis is (E) tert-butyl phenyl ether (t-butoxybenzene).

For example:

  1. Dimethyl ether: CH3OCH3
  2. Isopropyl ethyl ether: (CH3)2CHOCH2CH3
  3. 2-Ethoxybutane: CH3CH2CH2OCH2CH3
  4. Methyl phenyl ether: CH3OCH2C6H5
  5. Tert-butyl phenyl ether: (CH3)3COCH2C6H5

Learn more about Williamson ether synthesis here:

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