The following examination contains 32 questions valued at 3.5 points/question, and some rather tasty opportunities for extra credit
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1 Chem 131 Exam II Practice Spring 2018 The following examination contains 32 questions valued at 3.5 points/question, and some rather tasty opptunities f extra credit Name KEY 1. The cticosteroid prednisone suppresses the immune response and is useful in treating exposure to poison ivy and poison oak. Please list the functional groups present (HW 14.30) Prednisone Functional group 1: Alcohol (x2) Functional group 2: Ketone (x3) Functional group 3: Alkene (x2) While beyond the scope of this course, having both the alkene and alcohols at the carbon adjacent to the carbonyl (the carbon) influences their reactivities significantly. Make certain you do not confuse the terminal hydroxy ketone with a carboxylic acid, which connects oxygen directly to the carbonyl carbon Please name the following compounds. 1 EC point f crect alternative naming (I will use your best answer as the main answer, and if the 2 nd is a bit wobbly, I will use it as the extra credit) 2.
2 (in a pinch) 6. 7.
3 8. 9. If you have trouble seeing if different representations are the same molecule not, please feel free to bring ( beg f) model kits 10. Notice that even though the methyl group is indicated as directed towards the viewer, there are 2 of the same (ethylamino) groups; as such, (R) (S) isomers are not possible. Pure trickery! 11. F (preferred)
4 12. Please draw the structure of the following compounds directly below the name 13. butanedioic acid (succinic acid) 14. Dipotassium butanedioate (Dipotassium succinate) K + K Diethyl butanedioate (Diethyl succinate) 16. para-aminophenol
5 17. tho-chlo benzyl alcohol (2-chlophenylmethanol) 18. Triphenyl amine 19. Ethyl trans-2-hexenoate 20. Which of the following compounds would have the lowest boiling point? e.
6 Octane is non-polar. Only weak London fces hold a collection of octane molecules together. However the size (MM = 114 g/mol) does give a BP = o C. f comparison, heptanamide (MM = 129 g/mol) has a BP = 254 o C 21. Which of the following compounds would have the most limited water solubility? e. Like dissolves like and water is polar 22. Which of the following compounds would have the greatest solubility when mixed with a ph = 2 aqueous buffer? Acid will not react in low ph/acidic environment Amides are not basic e. N/A; All have about the same water solubility Weak base amine in acid bingo! Salt fms!
7 23. Which of the following compounds would have the greatest water solubility when mixed with a ph = 12 aqueous buffer? Acid in a basic environment bingo! Salt fms! Amides are not acidic either e. N/A; All have about the same water solubility Base will not react in a basic environment 24. Which of the following gives an acid when heated with aqueous HCl? e. N/A; all will give an acid when heated with aqueous HCl
8 Make certain you can name the acid fmed after hydrolysis in each case 25. Which of the following compounds will not dissolve completely in water? e. N/A; all of the above compounds dissolve completely in water Tough question, but recall esters are me limited in water solubility than one would expect based on carbon to oxygen ratio (pay close attention to page 5 of lecture 13 notes) In questions 25-30, please give the maj product f the following reactions. If there is no reaction, write N.R. 26. Room Temp Don t be fooled by the change in ientation, this is just a simple salt fmation between an acid and base 27.
9 28. Acid anhydride (similar to the acetic anhydride we used to make aspirin) allowing amide fmation between an amine and acid derivative, thus avoiding an acid-base reaction 1) KMnO4/OH - / NR No hydrogens available on the ketone f further oxidation 29. 1) NaBH4 2) H + Ketones resist further oxidation, but they can be readily reduced back to alcohols 30. H2O H + Recall Markovnikov s rule the most substituted alcohol is preferred 31.
10 H2O H + A bit tricky since the amine that initially went into making the cyclic amide (lactam) was part of the same molecule 32. Please synthesize pentanedioic acid from the -valerolactone (I) I Step 1: Aqueous acid and heat to generate 5-hydroxypentanoic acid Step 2: KMnO 4 in base with heat, Na 2 Cr 2 O 7 in H 2 SO 4 to oxidize alcohol to acid Bonus (3.5 EC): Please indicate a route by which styrene may be converted into acetophenone styrene acetophenone Step 1: Aqueous acid to generate 1-phenylethanol Step 2: KMnO 4 in base with heat, Na 2 Cr 2 O 7 in H 2 SO 4 to oxidize alcohol to ketone
The following examination contains 31 questions valued at 3.5 points/question. Please use a ½ sheet green Scantron for questions 1-23.
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