First Review Exam 1. 2. October 2000 *A* What is the structure of trans-3-methyl-3-hexene? A. B. C. D. Which one is the correct structure for vinyl chloride? A. 3. CHEM 2210, Organic Chemistry I Cl B. Cl C. Cl D. Cl What is the name of the compound shown? Cl OH Br A. B. C. D. 4. 2-bromo-6-chloro-5-methylcyclohexanol 2-bromo-6-chloro-5-methyl-1-cyclohexanol 6-bromo-2-chloro-3-methyl-1-cyclohexanol 6-bromo-2-chloro-3-methylcyclohexanol What functional group is present, if you have a broad absorption between 3200-3600 cm-1 ? A. Alkene 5. B. Alkane C. Alcohol D. Ketone Which of these IR frequency regions can you use to distinguish between a carboxylic acid and a nitrile? A. 2800-3000 cm-1 B. 1650-1780 cm-1 C. 1600-1620 cm-1 D. 1000-1500 cm-1 6. What functional group (groups) are present in the following compound? O N A. Carbonyl, 3˚ amine 7. C. Amide D. 3˚ amide Which of the following compounds is polar? A. BF3 8. B. Ketone, 3˚ amine B. BH3 C. SO 3 D. NH3 What is the total charge of the following species? H H O H Cl C C N H H H A. -1 9. B. 0 C. +1 D. +2 What is the hybridization of the indicated atom in the following species? H H O C C N CH3 Cl A. sp3 10. CH3 B. sp2 C. sp D. not hybridized Which of the following is a trans molecule? OH OH OH OH A. B. OH OH C. OH D. 11. Which of the following molecules has no 2˚ hydrogen(s)? A. B. C. D. Cl 12. Which of the following molecules has the LOWEST boiling point? A. B. C. D. OH 13. What is the common name for (CH3 )2 CHCH 2 Cl? A. tert-butylchloride B. sec-butylchloride C. neopentylchloride D. isobutylchloride 14. What is the IUPAC name of the following compound? A. bicyclo[4.3.0]decane B. 2-methylbicyclo[4.3.0]nonane C. 9-methylbicyclo[4.3.0]nonane D. 7-methylbicyclo[4.3.0]nonane 15. Which of the following compounds is NOT an isomer of the others? A. 16. O B. O C. OCH 3 OH D. Which of these is a sigma bonding orbital arising from the overlap of an s and an sp3 hybridized atomic orbital? A. B. C. D. 17. Which of the indicated carbon-carbon bonds is the longest? CH2 CH3 I A. I 18. B. II CH CH CH CH2 III II C. III D. All are the same length. An oxygen-containing compound does not have an IR peak at 1630-1780 cm-1 but it does have an absorption at about 3200cm-1 . O O OH NH 2 C CH C OH 3 A. 19. B. C. D. What is the geometry around the highlighted atom? CH3 CH= C-CH2 CH3 | OCH 3 A. Bent 20. C. Trigonal planar D. Trigonal pyramid What is the direction of the dipole moment of the molecule shown? F | C Br F F A. 21. B. Linear B. C. D. What species act as acids in the reaction shown? HCOOH + H3 PO 4 I II H2 PO 4 – + HCOOH2 + III IV A. I and III B. I and IV C. II and III D. II and IV 22. 23. 24. Which of the following is a secondary amine? H | O N || A. C. NH 2 B. CH3 CH2 C-NHCH 3 Which of the following compounds is different from all the others? A. Isobutyl chloride B. 1-Chloro-3-methylbutane C. ClCH2 CH2 CHCH 3 | CH3 D. Cl Which of the following compounds is bicyclo[3.1.1]heptane? A. 25. D. (CH3 CH2 )2 NCH 3 B. C. What is the IUPAC name of the compound shown? CH3 CHCH 3 | HOCHCH2 CH2 CHCH 3 | CH3 A. B. C. D. 2,6-dimethyl-3-heptanol 1,3-diisopropyl-1-propanol 2,6-dimethylheptanol 5-isopropyl-2-methyl-3-pentanol D.