Test #1 CH 226 Spring 2021 1 Test #4 This exam has 7 questions for a total point value of 100. Please check before submitting to make sure all questions are answered. Honor pledge: I have not been...

Provide a stepwise mechanism for the following reactions.


Test #1 CH 226 Spring 2021 1 Test #4 This exam has 7 questions for a total point value of 100. Please check before submitting to make sure all questions are answered. Honor pledge: I have not been given nor have I received unauthorized help on this test. Name___________________________________________________________ Signed _____________________________Date_________________________ CH 226 Spring 2021 2 CH 226 Spring 2021 3 1. Give the missing starting reagent(s) or major product of the following reactions (3 points each, total 36 points). a. 1. NaOEt 2. Br 5. H3O +, ∆ O O O O 3. NaOEt 4. Br N H N b. NaOH ∆ O c. LDA, -78oC Br O d. 1. 2. H3O + CuLi 2 O e. NaH, 25oC Br O f. NaOH Low tempertaureH H O + O g. NH+ H+ catalystO CH 226 Spring 2021 4 h. 1. I2, NaOH 2. H3O + O i. + H + catalyst H2N O O j. 1. NaOEt 2. Br 5. H3O +, ∆ O O O 3. NaOEt 4. Br k. l. 2. Provide a stepwise mechanism for the following reactions. (10 points each, 20 points total) NaOH ∆ OO HO OH + H + catalystO BrMg1. 2. H2O O CH 226 Spring 2021 5 N H O H O H H 3. Provide a stepwise mechanism for the following reactions. (14 points each, 14 points total) 1. NaOEtO O O Br 2. 3. H3O +, ∆ CH 226 Spring 2021 6 4. Propose a multi-step synthesis for the following compounds based on the starting material provided. Pick TWO out the four to answer and clearly indicate which problem you are answering. You must show all intermediate compounds of the synthesis. You can use ANY other reagents. (6 points each, 12 points total) a. Target product Starting material O H b. Target product Starting material OH O OH CH 226 Spring 2021 7 c. Target product Starting material OH OH HO O OH O d. Target product Starting material Br O HN CH 226 Spring 2021 8 5. Rank the following compounds in order of their acidity. Justify your ranking. (6 points) A B C D > > >OH O F F F OH O Cl Cl Cl OH O Br Br Br OH O Br Br Br 6. Provide structure for the following compounds. (3 points each, total 6 points) 2,2-diethyl-3-hexynoic acid N-butyl-N-propylpentanamide 7. Name the following molecules using the IUPAC system. (3 points each, total 6 points) H O Cl O CH 226 Spring 2021 9 Bonus 1: The reversible formation of cyclic hemiacetal formation is an important reaction in biochemistry. Provide a stepwise mechanism for the following reaction, which is the ring-opening of hemiacetal. (+6 points) O OH H O HO O HH H Bonus 2: Propose a multi-step synthesis for the following compound based on the starting material provided. You must show all intermediate compounds of the synthesis. You can use ANY other reagents. (+4 points) Target product Starting material OH OH O O Note that you may do both of the bonus problems for credit. It is not an either/or situation.