Practice Homework Iverson CH320M/328M Do not turn in. NAME (Print): Chemistry 320M/328M Dr. Brent Iverson Practice Homework December 3, 2018

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1 Practice omework Iverson C320M/328M Do not turn in NAME (Print): SIGNATURE: Chemistry 320M/328M Dr. ent Iverson Practice omework December 3, 2018 Please print the first three letters of your last name in the three boxes 1

2 Practice omework Iverson C320M/328M Do not turn in Score: 2

3 Practice omework Iverson C320M/328M Do not turn in Fill in the boxes with the structures that complete the reactions. Use wedges and dashes to indicate stereochemistry when appropriate. 1) 3 2) (C 3 ) 2 S 2 S 4 2 Cl Cl 2 1) B 3 2) 2 2 / NBS hν RR hν 2 2 1) s4 2) NaS 3 / 2 3

4 Practice omework Iverson C320M/328M Do not turn in Fill in the boxes with the structures that complete the reactions. Use wedges and dashes to indicate stereochemistry when appropriate. C 3 S C 3 Na NaCN NaSC 3 NaCN KtBu Na C 3 S C 3 4

5 Practice omework Iverson C320M/328M Do not turn in Fill in the boxes with the structures that complete the reactions. Use wedges and dashes to indicate stereochemistry when appropriate. NaN 3 Compare stereochemistry P 3 MeS 2 Cl NaN 3 2 Cr 4 2 S 4 1) s 4 2) NaS Cr 4 SCl 2 PCC 5

6 Practice omework Iverson C320M/328M Do not turn in Fill in the boxes with the structures that complete the reactions. Use wedges and dashes to indicate stereochemistry when appropriate. gs 4 2 S 4 2 1) NaN 2 2) 2 Cl 2 1) (sia) 2 B 2) 2 2 / 2 2 Cl Lindlar Catalyst 2 Lindlar Catalyst Na N Pd 6

7 Practice omework Iverson C320M/328M Do not turn in Fill in the boxes with the structures that complete the reactions. Use wedges and dashes to indicate stereochemistry when appropriate. This format is intended to get you more comfortable with working backwards in synthesis problems. 1) 3 2) (C 3 ) 2 S racemic NBS + hν racemic 2 Lindlar Catalyst 2 hν RR hν + racemic 7

8 Practice omework Iverson C320M/328M Do not turn in Fill in the boxes with the structures that complete the reactions. Use wedges and dashes to indicate stereochemistry when appropriate. This format is intended to get you more comfortable with working backwards in synthesis problems. 1) (sia) 2 B 2) 2 2 / PCC 1) s4 C 3 C 3 2) NaS 3 / 2 2 racemic 2 racemic 1) NBS / hν 2) 2 / Pt 8

9 Practice omework Iverson C320M/328M Do not turn in (3 or 5 pts each) Draw structures to complete the reactions. Use wedges and dashes to indicate stereochemistry and be sure to write racemic when appropriate s 4 2. NaS 3 1. C 3 C NaN 3 tbuk Na Cl Na 9

10 Practice omework Iverson C320M/328M Do not turn in (3 or 5 pts each) Draw structures to complete the reactions. Use wedges and dashes to indicate stereochemistry and be sure to write racemic when appropriate. C 3 Na C 3 C 3 2 S 4 (cat.) C 3 C 3 2 S 4 (cat.) 2 Cr 4 PCC C 3 S 2 Cl P 3 10

11 Practice omework Iverson C320M/328M Do not turn in (3 or 5 pts each) Draw structures in the boxes to complete the reactions. Use wedges and dashes to indicate stereochemistry and be sure to write racemic when appropriate. 2 hν Na, RR hν NaCN C 3 C Cr 4 11

12 Practice omework Iverson C320M/328M Do not turn in (3 pts each) Fill in the boxes with the structures that complete the reactions. Use wedges and dashes to indicate stereochemistry when appropriate. This format is intended to get you more comfortable with working backwards in synthesis problems. 1) 3 2) (C 3 ) 2 S 1) s4 2) NaS 3 / Racemic NBS + hν racemic Na N 3 1) (sia) 2 B 2) 2 2 / PCC 2 racemic 12

13 Practice omework Iverson C320M/328M Do not turn in (7-9 pts each) Draw structures for the product(s) of the following series of reactions. Use wedges and dashes to indicate stereochemistry when appropriate. This format is intended to get you more comfortable with working backwards in synthesis problems. 1) B 3 2) 2 2 / 3) PCC 1) 2 2) 3 NaN 2 3) Mild acid 4) (sia) 2 B 5) 2 2 / 1) 2 / hν 2) C 3 C 2 3) 2 S 4 / 2 13

14 Practice omework Iverson C320M/328M Do not turn in These are synthesis questions. You need to show how the starting material can be converted into the product(s) shown. You may use any reactions we have learned. Show all the reagents you need. Show each molecule synthesized along the way and be sure to pay attention to the regiochemistry and stereochemistry preferences for each reaction. Remember, when doing synthesis problems you should 1) count carbon atoms in the product and starting material(s), 2) work backwards and 3) RECGNIZE key features of a molecule that help you predict the reaction used to construct it. (10 pts)? 14

15 Practice omework Iverson C320M/328M Do not turn in You need to show how the starting material can be converted into the product(s) shown. You may use any reactions we have learned. Show all the reagents you need. Show each molecule synthesized along the way and be sure to pay attention to the regiochemistry and stereochemistry preferences for each reaction. (7 pts)? 3 C 3 C C 3 C 3 racemic 15

16 Practice omework Iverson C320M/328M Do not turn in You need to show how the starting material can be converted into the product(s) shown. You may use any reactions we have learned. Show all the reagents you need. Show each molecule synthesized along the way and be sure to pay attention to the regiochemistry and stereochemistry preferences for each reaction. (4 pts.)? (9 pts.)? 16

17 Practice omework Iverson C320M/328M Do not turn in You need to show how the starting material can be converted into the product(s) shown. You may use any reactions we have learned. Show all the reagents you need. Show each molecule synthesized along the way and be sure to pay attention to the regiochemistry and stereochemistry preferences for each reaction. All of the carbon atoms of the product must come from the starting material. (21 pts)? 17