Name: Date: I. Multiple Choice (Circle the letter for the best answer)
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1 Organic Chemistry II Sample Exam 3 You should also be able to name compounds, draw structures from names, and complete reactions given the reactants and conditions of the reaction. Name: Date: I. Multiple Choice (Circle the letter for the best answer) 1. Which compound would be most acidic? CH 3 CH 2 CH 3 CH 3 CH CH 2 Cyclohexane Benzene 2. What would be the major product of the following reaction? Page 1
2 3. What would be the major product of the following reaction at 100 C? I II III IV V 4. Which is the only one of these compounds which cannot self-condense in the presence of dilute aqueous alkali? Phenylethanal Propanal 2-Methylpropanal 3-Methylpentanal 2,2-Dimethylpropanal 5. Which of the following compounds would be the strongest acid? CHF 2 CH 2 CH 2 COOH CH 2 FCHFCH 2 COOH CH 3 CF 2 CH 2 COOH CH 3 CH 2 CF 2 COOH CH 3 CH 2 CH 2 COOH Page 2
3 6. What would be the major product of the following reaction? 7. Choose the reagent(s) that would bring about the following reaction: CH 3 CH 2 CH 2 COOH H 2 /Ni Li/liq NH 3 LiAlH[OC(CH 3 ) 3 ] 3 NaBH 4, CH 3 OH LiAlH 4, ether CH 3 CH 2 CH 2 CH 2 OH Page 3
4 8. What would be the product, C, of the following reaction sequence? (CH 3 ) 3 CCH 2 CH 2 CH 2 OH 9. What would be the product, C, of the following reaction sequence? (CH 3 ) 3 CCH 2 CH 2 CH 2 OH Page 4
5 10. What would be the major product of the following reaction? 11. The IR spectrum of a compound exhibits a broad absorption band at cm -1 and a sharp band at 1710 cm -1. Which of these compounds could it be? 1-Butanol Propyl acetate Butanoic acid Acetyl chloride Acetic anhydride Page 5
6 12. What would be the major product of the following reaction? I II III IV V 13. In which of the following sequences are the compounds listed in order of decreasing acidity? CH 3 COOH > H 2 O > CH 3 CH 2 OH > HC CH > NH 3 CH 3 CH 2 OH > CH 3 COOH > H 2 O > HC CH > NH 3 CH 3 COOH > CH 3 CH 2 OH > H 2 O > NH 3 > HC CH H 2 O > CH 3 COOH > CH 3 CH 2 OH > HC CH > NH 3 CH 3 CH 2 OH > H 2 O > CH 3 COOH > HC CH > NH While the IUPAC name for HCO 2 H is methanoic acid, it is commonly known as. Page 6
7 15. Which of these is a product of the reaction of C 6 H 5 MgBr with 17. Ethanoic acid (CH 3 CO 2 H) is usually called, from the Latin for vinegar. Page 7
8 18. What is the product of the reaction below? I II III IV V Page 8
9 20. Which reagents would you use to synthesize this compound by an aldol condensation? 21. What is the structure for J? I II III IV V Page 9
10 22. Which of these is not among the reaction products when a crossed aldol addition occurs between ethanal and butanal? 23. Which reagent would best serve as the basis for a simple chemical test to distinguish between NaOI (I 2 in NaOH) Br 2 /CCl 4 CrO 3 /H 2 SO 4 NaHCO 3 /H 2 O Ag(NH 3 ) 2 + Page 10
11 24. What compound results from the aldol cyclization of I II III IV Both III and IV 25. The aldol cyclization of produces which of these? I II III IV V Page 11
12 26. The aldol reaction of cyclohexanone produces which of these self-condensation products? I II III IV V 27. Which reagent would best serve as the basis for a simple chemical test to distinguish between NaOI (I 2 in NaOH) Br 2 /CCl 4 CrO 3 /H 2 SO 4 NaHCO 3 /H 2 O Ag(NH 3 ) In a solution of acetic acid (pka=4.74) adjusted to a ph of 2.74, the ratio of acetate to acetic acid is 10 to 1. the ratio of acetate to acetic acid is 100 to 1. the ratio of acetate to acetic acid is 1000 to 1. the ratio of acetate to acetic acid is 1 to 10. the ratio of acetate to acetic acid is 1 to 100. Page 12
13 29. Which of the following represent tautomers? All of these None of these 30. Which of these compounds would exist in an enol form to the greatest extent? 31. If acetone is reacted with LDA followed by methyl bromide, the product is isopropyl alcohol. 2-butanol. 2-butanone. 3-methyl-2-butanol. acetone. Page 13
14 32. Which compound could be subjected to a haloform reaction to produce m-chlorobenzoic acid? I II III IV V Page 14
15 35. A compound, X, C 9 H 10 O, gives a strong IR absorption peak at 1690 cm -1 and gives the following 1 H NMR spectrum. Triplet, 1.2 Quartet, 3.0 Multiplet, 7.7 Which is a possible structure for X? Page 15
16 36. Predict the major organic product of the reaction sequence below I II III IV V II. Mechanism (8 points) Using the curved arrow notation and showing all charges on ions and atoms, show the mechanism of the aldol condensation reaction of propanal with itself. how the steps for the formation of the enolate ion, the attack of the enolate ion, and any protonation or deprotonation reactions that may occur. If acid and heat are added after the reaction has occurred, what product would be produced? Page 16
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