Write your name and date on the cover page Do not open exam until instructed to do so

Transcription

1 Write your name and date on the cover page Do not open exam until instructed to do so Name: Date: Exam II Practice Exam Chem. 212 Do not open exam until told to do so. Get out your pencil, eraser, and scientific nongraphing calculator. Put everything else under the desk or on the floor. Turn off or silence then stow all electronic devices. You may leave the exam room after turning in your exam. You may not return to the exam room after leaving (until the exam is over). Provide the best answers as requested. You must show work for credit. Label your work should you use the back side of the paper. If you have any questions during the exam, write them on the exam. When told to do so, check that exam has all of its pages. 1 of 10

2 Q)Write the base catalyzed product(s) for chlorination of cyclobutanone N2 Q) Provide an IUPAC name for this compound: 2-nitrobenzoic acid C Q) Select the best answer for the effect of a chloro (-) substituent on benzene for electrophilic aromatic substitution A. activates the ring and directs ortho/para B. deactivates the ring and directs meta activates the ring and directs meta D. deactivates the ring and directs ortho/para E. no net activation and directs to ortho, meta, and para (D) Q)Provide the product of this reaction of 3-chloropropanal: C2C2C 2N3 C2C2C2 ( 2N2 2) Q) Which compound has the smallest pka? A. C B. C2 C D. C E. ( CC2 Q) Select the resonance structure of the intermediate that most destabilizes electrophilic (E ) attack of (trifluoromethyl)benzene at the para position. Lone pairs of electrons are not shown in the diagrams. A. E 2 of 10

3 B. D. E. (E) E E E E Q) Provide the product of this reaction: C2Li C2 1) C2C2 TF 2), 2 N2 Q) Which answer best explains the result from nitration of this compound A. nitration occurs predominantly ortho to -N2 B. nitration occurs predominantly ortho to - nitration occurs predominantly ortho to -C D. nitration occurs predominantly meta to - E. nitration occurs predominantly para to -N2 (B) Q) Provide the product of this reaction: 3 3 3C2C2CBr C2CBr 3C2C2C C2C PBr3 C Q) Provide the product of this reaction: C65CC()2 I LDA C65CC()3 Q) Provide the product of this reaction: C2Br KCN 1) C2C2 Acetone 2), 2 Q)Predict the product(s) of this reaction: N2 3Br2 2 C C 3 of 10

4 Br Br N2 Br Q) Provide the product of this reaction: 3C2C2CCC2C2C C2CCC2 3C2C2C C2C 3C2C2C C2C Δ!Li (C2)2, 2 Q)Which of the following contains a hemiacetal? C2 A. B. C2C C D. C E. ( 4 of 10

5 Q) Provide the product of this reaction after aqueous workup: C NaB4 C2 C C2 Q) Select the major product of this reaction: A. B. D. (B) C 3C2C C! Q) Which of these is the fastest toward electrophilic aromatic substitution? 5 of 10

6 A. 3C B. F3C D. F3C E. ( C N NaCN 3! CC C(C2)3 TMEDA CC C(C2)3 N2 PBr3 N2 Cr3, 2S4, acetone, 0 C 1. Br2, FeBr3 Q) Provide 1. the Br2, enolate FeBr3 ion that 1. arises 2S4, from N3 deprotonation of C C2 3C 2. C2Br, Al3! 2. 2S4, N3 2. Br2, FeBr3! 3C C2CCC2! C2C BrC2CCC2Br N2 C N2 C 2N C 1. C, Al3 1. Br2, FeBr3 2. Br 2, FeBr 3 2. C 3C, Al 3 1. Br 2, Br 3. Zn(g), Q) Provide 3. the Zn(g), product of this reaction: 2. N 3 C2CC N2 CC2 1. S 3, 2S 4 C2C2C2C 1. Br 2, N 3 2. N 3, 2S , Pd C 3. Zn(g), N2 1. N 3 2. FeBr 3 C 2N Q) Select the best synthesis for the reaction below:. NaN 2 1. Na, N S 4. S 3, 2S S2N 4 2. Na, S3N 3. S 3, 2S 4 1. N 3, 2S 4. N 3, 2S 4 2. S 3, 2S 4. Zn(g), 3. Zn(g), A. 2N C2Li, 2 C 6 of 10

7 1. N3, 2S4 2. Zn(g), 3. S3, 2S4 4. C3 B. 1. N 3, 2S 4 2. Zn(g), 3. S 3, 2S 4 1. S 3, 2S 4 2. N 3, 2S 4 3. Zn(g), D. 1. Na, N S 4 E. (B, Sulfonation conditions in step 3 are milder) C2C2C2C 2S4, 2 C2C CC2 2,, gs4 C2CC2C2 Q) Rank these compounds in the order of decreasing reactivity toward electrophilic aromatic substitution. (a) (b) Fastest to slowest A. a > b > c B. b > a > c c > a > b D. a > c > b E. b > c > a (E) (c) Q) Provide the product of this reaction: C2CC C2K, C2C2, (C2)2 7 of 10

8 C2C2C Q) Provide the product of this reaction run at low temperatures (5 C): Na C C (C611)2B CC2 TF 22, Na, 2 C C Br2, P (trace) Br C2CN 3C2C2C C2C N2 CR!C Δ Q) Provide the IUPAC name of this compound: cyclopentanecarboxylic acid C 1) Al3 2), 2 C 8 of 10

9 Q)Provide the product of this reaction:! Na, Q) Provide the product of this reaction: C N2 C2N CC2C 3, C22 Zn, C232 C2C2 PCC,C22 C2C Q) Which benzene ring is deactivated relative to benzene? A. N2 B. 3C D. C E. C 3 (C) CC2 MgBr Mg 9 of 10

10 Q) Provide the product of this reaction: 3CC N2N2, 2,!, triethylene glycol, Δ C2 Q) Provide the product of this reaction: 2 Q) Predict the product of this reaction: 1) Na 2) Δ Q) Provide the product of this reaction: C2C2C2 ()2CuLi C2C2C2Br Q) Provide the product of this reaction: 1) N! 2) I 3), 2 10 of 10