CHM 2120 : 2120 Blackboard problem set 1 2013 Answers - SN1 E1 E2 reactions(1).pdf
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Blackboard problem set 1 answers: predict the sn1 products of the following reactions. If no reaction is possible, write nr in place of the products. Write a mechanism for each transformation: a) predict the sn1 product of the reaction of (ch3)3ccl with 1-cyclohexylmethanol. Note: it is easier to do part b first: write a mechanism for the reaction. Cl: give two ways in which the reaction could be accelerated. Change the leaving group to i- or br- Perform the reaction in cyclohexylmethanol as solvent (protic solvent) Blackboard problem set 1 answers: for the following, predict which set of reaction conditions will give the fastest reaction. Water solvates the carbocation thus lowering its energy and lowering the activation energy relative to the reaction in acetone. Water also hydrogen bonds to br- as the c-br bond is breaking. This makes the c-br bond easier to break accerating the reaction b) The leaving group in the first reaction is terrible (oh-).
