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Reactions of Ethers

Reactions of Ethers

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Published by: Almira Bhel Morquianos on Mar 04, 2014
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Reactions of Ethers

Although ethers are relatively inert toward reaction, they usually show good solvent properties for many nonpolar organic compounds. This strong dissolving power coupled with low reactivity makes ethers good solvents in which to run reactions.

An acid‐catalyzed cleavage that occurs when hydriodic acid (HI) mixes with ethers is the most significant reaction that ethers experience. This reaction proceeds via a nucleophilic substitution mechanism. Primary and secondary alkyl ethers react by an S N2 mechanism, while tertiary, benzylic, and alcylic ethers cleave by an S N1 mechanism. A typical S N2 reaction would be the reaction of ethylisopropyl ether with HI. The mechanism for this reaction is:

Notice that for S N2 substitution, the alkyl halide came from the less sterically hindered group. For S N1 type reactions, the alkyl halide forms from the fragment of the original molecule that forms the more stable cation. Thus, the reaction of t‐butyl ethyl ether with HI gives t‐butyl iodide and ethyl alcohol. The following mechanism occurs:

this would be a less stable arrangement. determined by the shape of the ether. Some of E1’s alkene product. HI and HBr are often used.Notice that if the original ionization of the t‐butyl ethyl ether formed a t‐butoxide ion and an ethyl carbocation. . as always.) Acid Cleavage of Ethers Ethers are generally unreactive to most species. will be mixed in if SN1 occurs. The products separate in either an SN1 or SN2 style process. however. the order of stability of carbocations is 3° > 2° > 1°. With strong acid. ethers undergo a cleavage through a process begun by protonation of the ether oxygen. the halide anion serving as nucleophile. (Remember.

Ethers Worksheet Print this worksheet and give it a try! Answers For the following molecules. give the correct name. Good luck! 1) .

2) CH3CH2CH2CH2–O–CH2CH2CH2CH2CH3 3) 4) 5) 6) 7) 8) 9) 10) 11) 1) diethyl ether or ethoxyethane 2) butyl pentyl ether or butoxypentane .

3) pentyl propyl ether or pentyloxypropane 4) t-butyl isopropyl ether 5) butyl phenyl ether or phenyloxybutane 6) benzyl methyl ether or benzyloxymethane 7) 2-ethoxypentane 8) 3-ethoxy-3-propanol or 3-ethoxypropan-3-ol 9) 2-chloro-5-methoxy-3-pentanol or 2-chloro-5-methoxypentan-3-ol 10) furan 11) This one is for fun! "propyl people ether" .

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