1. Draw line-angle pictures of each of the following (include dashes/wedges where necessary to show stereochemistry).

Transcription

1 1. Draw line-angle pictures of each of the following (include dashes/wedges where necessary to show stereochemistry). (C 3 ) 2 CCC 2 C C C N C C 3-bromo-2-methyl-2-hexene (2R,3S)-2,3-dichloropentane cis-1,3-dimethylcyclohexane 2. Fill in the labels s, p, d, f, sp, sp2, sp3, σ, or π as appropriate. 3 C C

2 3. For each pair, circle the lower energy species. If they are the same, write 'same'. C 3 C 3 C 3 3 C C 3 C 3 transition state for a slower reaction transition state for a faster reaction starting material in an endothermic process product in an endothermic process

3 4. Label the relationship between each pair as identical, constitutional isomers, enantiomers, diastereomers, or unrelated. F E-2-fluoro-2-pentene 5. Name this. Include steroechemistry.

4 6. Predict the major organic product or products for each of the following. Be sure to include stereochemistry where important. C N (concentrated) 2 S 4 (concentrated) a) Mg b) 2

5 7. Predict the major organic product or products for each of the following. Be sure to include stereochemistry where important. 3 C heat heat 2 light a) B(Sia) 2 b) 2 2, Na a) B 3 b) 2 2, Na 2 Pd/CaC 3 /Pb 2 Pd

6 8. Suggest reagents for each of the following 9. Suggest starting materials for each of the following. a) C 3 Mg b) + 2 Pd a) 2, light b)

7 10. Provide reagents for each step of this multi-step synthesis. 11. Provide reagents for each step of this multi-step synthesis. 12. Give the product at each step of this multi-step synthesis. 2 light N Li a) 3 b) DMS 13. Give the product at each step of this multi-step synthesis. Li N 3(l) 2 2

8 14. Propose multi-step syntheses for these. multiple steps multiple steps S multiple steps C 3

9 15. Suggest mechanisms for these transformations. 2 heat 2 light Na

10 1. Draw line-angle pictures of each of the following (include dashes/wedges where necessary to show stereochemistry). (C 3 ) 2 CCC 2 C C C N C C N 3-bromo-2-methyl-2-hexene (2R,3S)-2,3-dichloropentane cis-1,3-dimethylcyclohexane 2. Fill in the labels s, p, d, f, sp, sp2, sp3, σ, or π as appropriate. 3 C C s σ sp3 sp3 σ s σ sp2 σ sp3 sp2 sp3 σ p p π σ sp2 sp2 sp2 sp2 s s

11 3. For each pair, circle the lower energy species. If they are the same, write 'same'. C 3 C 3 C 3 3 C C 3 C 3 same transition state for a slower reaction transition state for a faster reaction starting material in an endothermic process product in an endothermic process

12 4. Label the relationship between each pair as identical, constitutional isomers, enantiomers, diastereomers, or unrelated. unrelated diastereomer enantiomer F E-2-fluoro-2-pentene diastereomer 5. Name this. Include steroechemistry. (2R,4R)-2-chloro-4-methylnonane

13 6. Predict the major organic product or products for each of the following. Be sure to include stereochemistry where important. C N N (concentrated) 2 S 4 (concentrated) a) Mg b) 2

14 7. Predict the major organic product or products for each of the following. Be sure to include stereochemistry where important. 3 C heat (±) 3 C heat 2 light (±) a) B(Sia) 2 b) 2 2, Na a) B 3 b) 2 2, Na (±) 2 Pd/CaC 3 /Pb 2 Pd

15 8. Suggest reagents for each of the following a) 3 b) DMS a) LiAl 4 b) + 9. Suggest starting materials for each of the following. a) C 3 Mg b) + 2 Pd a) 2, light b)

16 10. Provide reagents for each step of this multi-step synthesis. a) NaN 2 b) 2 Lindlar mcpba a) C 3 Mg b) Provide reagents for each step of this multi-step synthesis. 2 NaN 2 a) B 3 light b) 2 2, Na 12. Give the product at each step of this multi-step synthesis. N 2 light Li a) 3 b) DMS 13. Give the product at each step of this multi-step synthesis. Li 2 (±) N 3(l) 2

17 14. Propose multi-step syntheses for these. multiple steps a) NaN 2 b) C 3 2 Lindlar's a) NaN 2 b) C 3 C 2 Note, the order of the first two steps could be switched. multiple steps S 2, light + SC 2 C 3 In step 2, any strong bulky base. Alternatively, you could do an SN2 from the bromocyclohexane. N Li multiple steps C 3 2, light + C 3 N Li mcpba Again, any strong base would be fine in step 2.

18 15. Suggest mechanisms for these transformations. 2 heat 2 light 2 light C 3 C 3 C 3 C 3 Na