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Unformatted text preview: 6-66 continued substitution on 20 carbocation substitution on rearranged 30 carbocation 6
_ H �H CH3 :6-CH
•• 3 .. CH3 ---- :O-CH3 •• -I� ... elimination from rearranged 30 carbocation a / �- CH3 :O-CH3 •• H
I .... H (a)
6-67 E2- one step CH3-CH-CH3 (� r (b) In the E2 reaction, a C-H bond is broken. When D is substituted for H, a C-D bond is broken, slowing the reaction. In the S N2 reaction, no C-H (C-D) bond is broken, so the rate is unchanged. (c) These are first-order reactions. The slow, rate-determining step is the first step in each mechanism. Br Explanation on next page H l slow... .. I, + fast :Br: H2C-CH-CH3 -- H2C=CH-CH3 E l H2C-CH-CH3 '-= :OH -- OH I CH3-CH-CH3 + Br- ( � SN I H3C-CH-CH3 (BI r H
I o: + slow ... H3 C-CH-CH3 -fast + Br127 � ...
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- Spring '10