5. (6 pts) Show how the following compound can be synthesized from the indicated starting material:
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1 Exam 2 Name CHEM (36 pts) Complete the following chemical reactions showing all major organic products; illustrate proper stereochemistry where appropriate. If no reaction occurs, indicate NR : a. b. c. d. e. f. g. h. i. j. k.
2 2. (8 pts) Consider the following substituted benzenes. For each example: a. Indicate whether the substituent is activating or deactivating (circle one) b. Indicate whether it would be ortho, meta or para directing (circle all that apply) 3. (6 pts) Nomenclature: Name the acids or provide a structure given the name. a. b. c. d. Succinic acid Potassium 2,3,5-trifluorohexanoate 4. (4 pts) In preparing for this exam you may have consumed caffeine, which inhibits the retention of short term memories (like organic exam chemistry knowledge). Is caffeine aromatic? State your reasoning. 5. (6 pts) Show how the following compound can be synthesized from the indicated starting material: 6. (8 pts) Show the contributing resonance structures following a para addition of an electrophile (E + ) to phenol. Circle the most stable resonance structure or structures.
3 7. (6 pts) We studied the EAS reaction of benzene. There are many other families of aromatic compounds that also undergo EAS reactions. Suggest the probable course of the EAS reactions of thiophene (right). a. Is the ring more or less electron rich than benzene? b. Would EAS reactions be faster or slower? c. What orientation of EAS would be most favored relative to the ring sulfur? Explain why. d. Draw the orbital diagram for thiophene; be sure to label all orbitals containing delocalized electrons and lone pairs. 8. (12 pts) Indicate if the anions would deprotonate the acid in each pair (Circle yes/no): g. h. i. a. b. c. d. e. f. 9. (6 pts) Synthesize m-methoxybenzyl cyanide from m-methylanisole: 10. (8 pts) Circle the compounds that are aromatic; for those that are not aromatic, briefly state which of the four criteria are not met. Approximate Course Grade: A A- B+ B B- C+ C D F Score /100
4 Exam 2 Name CHEM (36 pts) Complete the following chemical reactions showing all major organic products; illustrate proper stereochemistry where appropriate. If no reaction occurs, indicate NR : a. b. NR Friedel-Crafts conditions react with NH 2 c. d. e. f. g. h. i. j. k.
5 2. (8 pts) Consider the following substituted benzenes. For each example: a. Indicate whether the substituent is activating or deactivating (circle one) b. Indicate whether it would be ortho, meta or para directing (circle all that apply) 3. (6 pts) Nomenclature: Name the acids or provide a structure given the name. a. b. c. d. Succinic acid Potassium 2,3,5-trifluorohexanoate 4. (4 pts) In preparing for this exam you may have consumed caffeine, which inhibits the retention of short term memories (like organic exam chemistry knowledge). Is caffeine aromatic? State your reasoning. All atoms in both the 6 and 5 membered ring are (or can) be sp2 hybridized. Planar, cyclic 10 pi electrons 2 nitrogens in 6-membered ring with lone pairs, double bond bridging rings, C=N double bond in 5-membered ring and lone pair on N in 5-membered ring. Aromatic! 5. (6 pts) Show how the following compound can be synthesized from the indicated starting material: 6. (8 pts) Show the contributing resonance structures following a para addition of an electrophile (E + ) to phenol. Circle the most stable resonance structure or structures.
6 7. (6 pts) We studied the EAS reaction of benzene. There are many other families of aromatic compounds that also undergo EAS reactions. Suggest the probable course of the EAS reactions of thiophene (right). a. Is the ring more or less electron rich than benzene? b. Would EAS reactions be faster or slower? c. What orientation of EAS would be most favored relative to the ring sulfur? Explain why. d. Draw the orbital diagram for thiophene; be sure to label all orbitals containing delocalized electrons and lone pairs. a. Ring is more e- rich 6 p electrons for 5 atoms vs. 6 for 6 in benzene. b. EAS is faster for more e- rich systems c. Ortho (2-) addition additional resonance structure with sulfur Each p-orbital on C has one e-, on sulfur it has two; second lone pair on sulfur in sp 2 orbital 8. (12 pts) Indicate if the anions would deprotonate the acid in each pair (Circle yes/no): g. h. i. a. b. c. d. e. f. 9. (6 pts) Synthesize m-methoxybenzyl cyanide from m-methylanisole: 10. (8 pts) Circle the compounds that are aromatic; for those that are not aromatic, briefly state which of the four criteria are not met. Approximate Course Grade: A A- B+ B B- C+ C D F Score /100
Exam (6 pts) Show which starting materials are used to produce the following Diels-Alder products:
Exam 1 Name CHEM 212 1. (18 pts) Complete the following chemical reactions showing all major organic products; illustrate proper stereochemistry where appropriate. If no reaction occurs, indicate NR :
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