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1. Which one of the indicated atoms is sp2 hybridized? 2. What functional groups are present in capsaicin shown below? a. Amine, ester, arene b. Amide, ester, alkene c. Amine, ether, alcohol d. Amide, ether, alkene 3. Draw the Newman projection for the following molecule, sighting down the C2-C3 bond. 4. Draw all constitutional isomers for the following molecular formula: C3H6O (hint: calculating the index of hydrogen deficiency might be useful). CHE 230 – Organic Chemistry I Spring 2020, Dr. Mills 5. Starting with the ketone form shown below, show the mechanism for the acid-catalyzed keto-enol tautomerization to the enol form. 6. Select all of the following E, Z designations that are correct. (hint: there are actually answers this time). 7. Which of the following is an enantiomer of the following molecule? 8. Rank the following molecules from most basic (1) to least basic (4). 9. Which of the following molecules can undergo an SN1 reaction? 10. Which of the following is true about the reaction shown below? a. Multiple diastereomers are made b. Elimination products are obtained c. A single enantiomer is made d. A carbocation is made in the mechanism e. None of these 11. Draw the major product of the following reaction. 12. Draw the major product of the following reaction. 13. Which of the following functional groups did I discuss how to name on a chalkboard in one of my online lecture videos? a. Ketones b. Alcohols c. Aldehydes d. Carboxylic acids e. Amines 14. What product would be obtained from the following oxymercuration-reduction reaction? 15. Draw both of the missing structures for the following reaction sequence. 16. Draw the starting material that would be used to synthesize the following epoxide. 17. In the following mechanism, one arrow is incorrect. Which one? 18. Draw the complete mechanism for the following hydroboration-oxidation reaction and draw the major product. If there is a tautomerization step, you do NOT need to draw that part of the mechanism, simply write tautomerization over the arrow. You can use R groups to represent the structure of 9-BBN. 19. Draw the three missing structures for the following reaction sequence. 20. What is the IUPAC name for the following molecule? 21. What is the IUPAC name for the following molecule? 22. What is the IUPAC name for the following molecule? 23. Write the starting material and the reagents required to synthesize the following molecule. 24. Draw the complete mechanism for the following reaction and the major product. Make sure to draw any resonance structures. 25. Which elementary step does NOT occur in the mechanism for the following reaction? a. nucleophilic addition d. coordination b. nucleophile elimination e. proton transfer c. heterolysis 26. Which of the following compounds is aromatic? 27. How many π electrons contribute to the aromatic pi system in guanine, one of the four main bases found in DNA and RNA, shown below? a. 6 d. 14 b. 10 e. 20 c. 12 28. Which of the following molecules is antiaromatic? 29. Starting from acetylene (the alkyne shown below) and a 2 carbon alkyl halide, show how to make the indicated product. Show the reagents required for each reaction. (Hint: this synthesis requires more than one step).

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