EXAM 2 STUDY GUIDE

Hi guys! Please attempt these questions on your own before attending the exam review on Wednesday. My study tips for you would be to prioritize your book, homework problems, and the resources Dr. Daoudi provides. Please do not use this as your primary study method! I wish you all the best of luck studying.

NOTE: I will include more examples of chair conformation flips and going from line-angle to newman projections during the review.

1. Which of the following is not another representation for 2-methylbutane?

1. Which compounds (B-F) are identical to A? Which compounds (B-F) represent a constitutional isomer of A?

2. Give the IUPAC name for each compound

3. Give the structure corresponding to each IUPAC name

4. Give the structure corresponding to each IUPAC namea. 7-chloro-3-ethyldecaneb. 3-bromo-2,7-dimethyloctanec. 1-bromo-3-chlorocyclohexane

5. Give the IUPAC name for each compound

6. Arrange the following compounds in order of increasing boiling point

7. Which of the following is/are possible newman projections for 2-methylpentane

8. Rank the following in order of increasing energy

9. Identify the torsional and steric strain in each conformation

10. Using the cyclohexane with the C’s numbered as shown, draw a chair form that fits each description

11. Draw a second chair conformation for each cyclohexane. Then decide which conformation is present in higher concentration at equilibrium *more examples in review*

12. Name the following compounds:

13. For each compound below:

a. Label each OH, BR, and CH3 group as axial or equatorialb. Classify each conformation as cis or transc. Translate each structure into a representation with a hexagon for the 6-membered

ring, and wedges/dashes for groups above and below the ringd. Draw the second possible chair conformation for each compound (ring flip)

14. Locate the stereogenic centers in each molecule

15. Locate the stereogenic center in each compound and draw both enantiomers

16. Which group is assigned the higher priority?

17. Rank the following groups in order of decreasing priority

18. Label each compound as R or S.

19. Label the stereogenic centers and draw all possible stereoisomers. Label the enantiomers and diastereomers.

20. Label each as constitutional isomers, enantiomers, diastereomers, or neither.

21. Draw all the stereoisomers for each. Label them as enantiomers or diastereomers.

22. Give the IUPAC name for the compound, including the R,S designation for each stereogenic center