Reactions of Ethers and Epoxides

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CH₃CH₂CH₂Br +

Both S_N2 and S_N1 (and E1) reactions occur, depending on the substrate. If a phenyl ether is used, S_N2/S_N1 reaction occurs only on the alkyl carbon, leaving phenol as a product.
McMurry 18.5, Fessenden 8.3, Schmid 13.9

Epoxides

These strained ethers are very easy to make but very reactive toward nucleophiles; think of them as spring-loaded ethers. One enantiomer is shown for each starting material and product.

Stereospecific! Base-catalyzed ring opening is by S_N2 at the less substituted carbon.
McMurry 18.8, Fessenden 8.4, Schmid 13.12

Stereospecific! Base-catalyzed ring opening is by S_N2, at the less substituted carbon. Note that other nucleophiles , such as thiols, thiolates, cyanide, also will open the ring.
McMurry 18.8, Fessenden 8.4, Schmid 13.12

Stereospecific, giving the enantiomer of that shown. Acid catalyzed ring opening occurs via S_N1 on the protonated epoxide, on the more substituted carbon but with strong preference for the backside.
McMurry 18.8, Fessenden 8.4, Schmid 13.12

Stereospecific, as shown. Acid catalyzed ring opening occurs via S_N1 on the protonated epoxide, on the more substituted carbon but with strong preference for the backside.
McMurry 18.8, Fessenden 8.4, Schmid 13.12

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Last update Feb. 1, 1999