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Chapter 8 HW Problem Set Assigned Chapter 8 Textbook Problems (very important for problem practice): 7 th^ edition: 25b-e, 26, 30-31, 34-35, 36b-d, 37, 40-46, 48, 50-55, 65 8 th^ edition: same as the 7th^ edition 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. 25b counts as one problem). Insert a blank page if more space is needed.
Complete the following problems: Q1 : a) Arrange the compounds in order of decreasing p Ka, highest first. b) Circle the substrate that would not efficiently generate a Grignard reagent upon reaction with Mg in ether. c) Circle the Grignard reagents that contain incompatible functional groups. d) Circle the substrates that will give an achiral product after a Grignard reaction
with CH 3 MgBr.
Q2: Predict all organic product(s), including stereoisomers when applicable. a) OH (^) OH OH Cl OH Br OH Cl I Cl Br F MgBr O HO MgBr O MgBr HO MgBr MgBr MgBr H O (^) O O O O O OH PCC CH 2 Cl 2
Q3: Write in the starting alkyl bromide used to form the following products. Include any reactants, reagents, and solvents over the reaction arrow. If more than one step is required, denote separate steps by using 1), 2), 3), etc. Q 4 : Predict the organic products for the following reactions. Then draw curved arrow electron- pushing mechanism for the reactions. a) O NaBH 4 EtOH
b)
Q 5 : Propose a reasonable synthesis for the following decalin derivative. using only
decalin and alkanes of 3 or fewer carbons.
H O
MgBr
- Et 2 O
- H+, H 2 O
Decalin
