Which reaction below proceeds faster, (a) or (b) What is the product Explain.(a)Excess
Chapter 11, Problem 1-6(choose chapter or problem)
Which reaction below proceeds faster, (a) or (b)? What is the product? Explain.(a)Excess NaOH,CH3CH2OHCl%(b)Excess NaOH,CH3CH2OHClWhat does the question ask? Explain! Theres your cue: This is a mechanism problem.How to start? As in the preceding example, characterize the substrates: Here they aresecondary chloroalkanes, with additional steric hindrance on the adjacent carbon. Again,the reagent is a strong nucleophile and base.Information: Displacement by SN2 is unlikely; as in I-6, E2 should be favored(Table 7-4). What next?Proceed, logically: Use the question as a clue to how to proceed. Why should these tworeactions proceed at different rates? How do the substrates differ? Answer: stereochemically.So, redraw both starting materials in the more instructive cyclohexane chair forms:(a)ClAxial Cl is trans and antito hydrogen atomson the adjacent carbonsHHCH3H3C(b)Cl Equatorial Cl is cis andgauche to hydrogen atomson the adjacent carbons
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