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: xam II Practice xam 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 11

2 1)Write the base catalyzed product(s) for chlorination of cyclobutanone N2 2) Provide an IUPAC name for this compound: C 3) 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 C. activates the ring and directs meta D. deactivates the ring and directs ortho/para. no net activation and directs to ortho, meta, and para 4) Provide the product of this reaction of 3-chloropropanal: C2C2C 2N3 5) Which compound has the smallest pka? A. C B. C3C2 C. D.. 6) Select the resonance structure of the intermediate that most destabilizes electrophilic ( ) attack of (trifluoromethyl)benzene at the para position. Lone pairs of electrons are not shown in the diagrams. A. C3C C3CC3 CC2C3 B. D. C. 2 of 11

3 . 7) Provide the product of this reaction: C3C2Li C2 1) 2) TF, 2 N2 8) Which answer best explains the result from nitration of this compound A. nitration occurs predominantly ortho to -N2 B. nitration occurs predominantly ortho to -C3 C. nitration occurs predominantly ortho to -C D. nitration occurs predominantly meta to -C3. nitration occurs predominantly para to -N2 3C2C2C 9) Provide the product of this reaction: 3 C3C2C PBr3 10) Provide the product of this reaction: C65CC(C3)2 C3I 11) Provide the product of this reaction: C3C2Br KCN 1) 2) LDA Acetone C3 C PCC, 2 C3 Py, Cr3 -, C22 N Pyridinium chlorochromate Cr3, C22 12) Predict the product(s) of this reaction: 3Br2 13) Provide the product of this reaction: C3C2C C3C2C C C2 Br 14) Provide the product(s) of this reaction: C2C3 2CCC2C2C2C2C2C3 Br C2C3 2C3 C2 15) Which of the following contains a hemiacetal? BrC2CC2C2C2C2C2C3 C CC2C2C2C2C2C3 C2 C CC2C2C C C3I NaN2 C3 N3 C3C2I CC2C3 C3C2C2I C3C2C2C2I (C3)2C r Br C3C2C2C2Li, TF A. CC2C3 C C C B. C2C C3CC2 3C C C3C C C CC3 C CC2C3 C CC2C2C3 LiC CC2C3 Br C3CCC3 (C3)2C N2 2 C C 3C2C2C 3C2C2C Δ (C3)3C Li Li Diethyl ether (C3C2)2 Acetonitrile C3 DMF Dimethyl sulfoxide MPA ((C3)2N)3P Nitromethane N,N-dimethylformamide C2C2 Acetone Dimethyl formamide DMS examethylphosphoric triamide 3 of 11 C3CC3 C3CN CN(C3)2 (C3)2S C3N2 CN(C3)2 NaB4 LiAl4 (C3)3C Na2Cr27, 2S4, 2 3, 2 NaB4, C3C2 LiAl4, (C3C2)2 2 2CC Water thanol Methanol Isopropanol Propanol Formic acid Acetic acid Formamide N-methylformamide C (C C C

4 C. D. C C. 16) Provide the product of this reaction after aqueous workup: NaB4 C3C C3C2 17) Select the major product of this reaction: A. B. C. 4 of 11

5 D. 3C2C 18) Provide the product(s) of this reaction: C3C 19) Which of these is the fastest toward electrophilic aromatic substitution? A. 3C C3 B. C. F3C C3 D. C3. F3C 3 C2 TMDA PBr3 20) Provide the product(s) of this reaction: NaCN 3C C3 C2CCC2 21) Provide 3C C3the product(s) of this reaction: C3 CC C(C2)3C3 BrC2CCC2Br N2 N2 C N2 N2 C3 C3 22) Provide the enolate ion that arises from deprotonation of C 2N 2N C Cr3, 2S4, acetone, 0 C C3 C3C CC2C3 N2 N2 23) Provide the product of this reaction: C2CC C C 24) Select the best synthesis for the reaction below: 2N C3C2Li, 2 C 2N S3 5 of 11

6 A. B. C. D.. 1. N3, 2S4 2. S3, 2S4 3. Zn(g), 1. N3, 2S4 2. Zn(g), 3. S3, 2S4 4. C3 1. N3, 2S4 2. Zn(g), 3. S3, 2S4 1. S3, 2S4 2. N3, 2S4 3. Zn(g), 1. Na, N S 4 25) Provide the product(s) of this reaction: C2C2C2C 2S4, 2 26) Provide the product(s) of this reaction: C3C2C CC2C3 2,, gs4 27) Rank these compounds in the order of decreasing reactivity toward electrophilic aromatic substitution. (a) (b) (c) Fastest to slowest A. a > b > c B. b > a > c C. c > a > b D. a > c > b. b > c > a C3 28) Provide the product of this reaction: C2CCC3 C3C2K, C2C2, (C3C2)2 29) Provide the product of this reaction run at low temperatures (5 C): Na 6 of 11

7 30) Provide the product(s) of this reaction: C3C C (C611)2B TF 22, Na, 2 31) Provide the product(s) of this reaction: C Br2, P (trace) 32) Provide the product(s) of this reaction: C3C2C C3N2 3C2C2C CR C Δ 33) Provide the IUPAC name of this compound: C3 34) Provide the product(s) of this reaction: C3C Al3 1) 2), 2 35) Provide the product of this reaction:, 36) Provide the product of this reaction: C N2C3 37) Provide the product(s) of this reaction: 38) Provide the product(s) of this s reaction: C3C2C2 39) Which benzene ring is deactivated relative to benzene? A. B. C. 3C 3C C C3 (C3)2S C 3, C22 C2 Cr3, 2S4, 2 Zn, C232 N2 C C3C2MgBr, (C3C2)2 N2 C C3 3C N2 C C3 N2 C C N2 N2 Na (C3)2S Li C3(C3C2)2 C N2 Zn, C232, 2 PCC,C22 7 of 11

8 C3 D.. C3 C3 CC3 C3 40) Provide the product of this reaction: 3CC N2N2, 2,, triethylene glycol, Δ 41) Provide the product of this reaction: 2 Na 42) Predict the product of this reaction: 1) 2) Δ (C3)2CuLi 43) Provide the product of this reaction: C3C2C2C2Br N C3I, 2 44) Provide the product of this reaction: 1) 2) 3) 8 of 11

9 1) 2) 2-nitrobenzoic acid 3) D 4) C2C2C2 ( 2N2 2) 5) A 6) 7) C3C2C2 8) B 9) 3 3C2C2CBr C3C2CBr 10) C65CC(C3)3 11) C3C2C2 Br Br N2 12) 13) 14) 15) A 16) C3C2 17) B 18) 19) A 20) 21) 22) C2C resonance structure 23) 24) B 3C2C2CCC2C2C Br C3C2CCC2C3 C3C C N C3 CC C(C2)3C3 C3C2C2C2C 9 of 11

10 25) 26) 27) C3C2CC2C2C3 C2C2CC3 C3 28) C3 29) 30) 31) 32) C3C2CNC3 33) cyclopentanecarboxylic acid 34) CC2C3 C3C < C Br C3 35) 36) C2NC3 37) CC2C 38) C3C2C 39) C 40) C3C2 41) 42) 10 of 11

11 C2C2C2C3 43) C3 44) 11 of 11