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Solutions to Problems 355 36. 0 + H H CI S H⁺ + :0: H O H H + H :0 :0: H H SO₂ + + 37. (a) (b) 3-Pentanone + H₂C=CHCH₃ CH₂CH₃ (c) (d) 3-Pentanone + H₂C=C(CH₃)₂ CH₂CH(CH₃)₂ (b) and (d) show the results of E2 elimination: Alkylation requires an SN2 process and you already know that these are poor with secondary and impossible with tertiary haloalkanes. 38. Both are aldehyde enamine alkylation sequences. The new carbon-carbon bond is marked with an arrow. (a) (b) CH₂ CHCHO (via CH₂ Br + CH=CH-N SN2 reaction) 39. Illustrated with cyclohexanone: Before the reaction between cyclohexanone enolate and iodomethane has gone to completion, a mixture is present containing O 0 CH₃ : CH₃I, , and