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Dolbier HW Solutions 209 - 203 NUCLEOPHILIC SUBSTITUTION...

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8.39 The substrate is a tertiary alkyl bromide and can undergo S N 1 substitution and E1 elimination under these reaction conditions. Elimination in either of two directions to give regioisomeric alkenes can also occur. 8.40 Solvolysis of 1,2-dimethylpropyl p -toluenesulfonate in acetic acid is expected to give one substitu- tion product and two alkenes. Since fi ve products are formed, we are led to consider the possibility of carbocation rearrangements in S N 1 and E1 solvolysis. Since 2-methyl-2-butene is a product common to both carbocation intermediates, a total of fi ve dif- ferent products are accounted for. There are two substitution products: and three elimination products: 8.41 Solution A contains both acetate ion and methanol as nucleophiles. Acetate is more nucleophilic than methanol, and so the major observed reaction is: Methyl iodide CH 3 I Acetate CH 3 CO O Methyl acetate CH 3 OCCH 3 O methanol 2-Methyl-2-butene CHCH 3 (CH 3 ) 2 C 3-Methyl-1-butene
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