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159 Synthesize 2-methyl-2-pentanol Synthesize 2-methyl-2-pentanol from 1-butanol this can be accomplished by reacting two equivalents of a Grignard.
Synthesis of Alcohols Grignard or Organolithium –Reagents • B) 1-butanol • C) 3-hexanol • D) 3-pentanol Example (76%) H2C CHLi++ CH O 1.
However, a greater variety of mechanisms have a reasonable chance of participating.The loss of a proton from the tertiary carbocation gives two products, 2-methyl-1-butene and 2-methyl-2-butene.Addition of the HCl to these gives the desired 2-chloro-2-methyl butane.For preparation of 1-bromobutane:Mix 11.1 g NaBr + 10 mL H2O + 10 mL 1-butanol + 10 mL HCl in 100 mL RB flask; mix well while cooling in ice (must be in ice when 10 mL HCl is added), set up apparatus for reflux.Warm gently 30 min.Simple distillation--collect water and 1-bromobutane in ice-cooled receiver.
Title: Synthesis of 1-Bromobutane
If the solvent, such as a protic solvent, solvates the nucleophile too greatly, it cages it in to interfere with its ability to attack the substrate.The best solvent for SN1 reactions should be polar protic, to maximally stabilize the carbocation transition state and thereby lower the energy of activation.(Table 01)(Table 02)Note: 1-butanol and sodium bromide are used together as reactants for the first experiment, and 2-methyl-2-butanol and hydrochloric acid are used together as reactants for the second experiment.(These reactions and mechanisms are illustrated on separate paper.)Formation of 1-bromobutane from 1-butanol:This is a very simple reaction.