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Chapter 6 HW Problem Set Assigned Chapter 6 Textbook Problems (very important for problem practice): 7 th^ edition: 38 - 39, 41-49, 55-59 (46b not required) 8 th^ edition: 38 - 39, 41, 43-50, 57-61 (47b not required) Use all the assigned textbook problems above for practice. On this HW, show your work for five individual problems that you consider representative from the assigned textbook problems. (e.g. 46 a counts as one problem). Insert a blank page if more space is needed.
Complete the following problems: Q1 : Rank the relative nucleophilicity of the following species in ethanol. CH 3 O-, CH 3 OH, CH 3 COO-, CH 3 COOH, CH 3 S- Q2 : Group these solvents into either protic solvents or aprotic solvents. Acetonitrile (CH 3 CN), H 2 O, Acetic acid (CH 3 COOH), Acetone (CH 3 COCH 3 ), CH 3 CH 2 OH, DMSO (CH 3 SOCH 3 ), DMF (HCON(CH 3 ) 2 ), CH 3 OH Q3 : Arrange each group of compounds from fastest SN 2 reaction rate to slowest SN 2 reaction rate. a) b) Q4 : Rank the relative nucleophilicity of halide ions in water solution and DMF solution, respectively. F-^ Cl-^ Br-^ I- Q5 : Determine which of the substrates will and will not react with NaSCH 3 in an SN 2 reaction to have a reasonable yield of product. Cl Cl H 3 C Cl Cl Br Br Br H 3 C Br NH 2 Br^ Br Br (^) OH Br
A B C D
A B C D
b) c) d) e) f) g) h) Br H
solvent O D D
i) Q 10 : (a) Propose a synthesis of C from A. (b) Propose a synthesis of C from B. A B C
