PRACTICE FIRST HOUR EXAM A 1. Which of the following compounds is the most soluble in water? A. B. C. D. 2. ORGANIC CHEMISTRY 2210 CH3 CH2 CH2 OH CH3 CH2 CH2 Br (CH3 )2 CHCH 2 OH (CH 3 )2 CHCH 2 Br What species act as bases in the reaction shown? H2 SO 4 + CH3 COOH I A. I and III 3. II III B. I and IV C. II and III B. 12 C. 14 D. II and IV D. 16 What is the direction of the dipole moment in the molecule shown? Cl H C=C Cl A. 5. IV How many hydrogen atoms are present in a molecule of tetralin? The structure of tetralin is given below. A. 10 4. HSO 4 – + CH3 COOH 2 + B. Cl C. D. What is the IUPAC name of the molecule shown? A. B. C. D. H3 C CH3 | | Cl-C—C-H | | H3 C CH3 1-chloro-1,1,2,2-tetramethylethane 2-chloro-2-isopropylpropane 2-chloro-2,3-dimethybutane 2-chlorohexane 29 6. Which of the following gives a peak at 1710 cm-1 in its IR spectrum? A. CH3 CH2 C=O B. CH 3 CH2 CHCH 3 C. CH3 CH2 CHOH D. CH3 CH2 CHNH 2 | | | | CH3 CH3 CH3 CH3 7. What is the predicted shape and bond angle for the species shown? Cl | :C—Cl | Cl A. B. C. D. 8. Trigonal planar, 120˚ Trigonal planar, 109.5˚ Trigonal pyramid, 120˚ Trigonal pyramid, 109.5˚ What are the respective hybridizations of the carbon atoms numbered 1 and 2 in the structure shown? 1 2 A. sp3 , sp2 9. C B. sp2 , sp C. sp, sp3 D. sp, sp Which of the following is a pair of resonance structures? A. :O: || °° H—C—O: °° °° C. H—C—C=C—H | | | H H H 10. C—H :O: || °° :O—C—H °° B. H—C=C—C—H | | | H H H ° H—C=C—C—H | | | H H H D. H :O: H | || / H-C—C—C-H | | H H What is the structure of neopentyl alcohol? A. (CH3 )3 CCH2 CH2 OH C. (CH3 )2 CHCH 2 CH2 CH2 OH B. (CH3 )3 CCH2 OH D. (CH 3 )2 CHCH 2 CH2 OH 30 H—C—C=C—H | | | H H H °° H :O-H | | H-C—C=C-H | | H H 11. What is the name of the compound shown? A. B. C. D. 12. Which of these statements is true of the molecule shown? A. B. C. D. 13. It contains five pi bonds. It contains seven sigma bonds. The H-C-H bond angle is 109.5˚. The hydrogen atoms are sp3 hybridized. H H | | H-C=C-C≡C-H What words complete the following sentence? (CH3 )2 COHCH 3 is a _______ alcohol, and (CH3 )2 CNH 2 CH3 is a _______ amine. A. B. C. D. 14. bicyclo[3.2.2]nonane bicyclo[4.2.1]nonane bicyclo[4.3.0]nonane bicyclo[5.2.0]nonane primary . . . tertiary tertiary . . . primary primary . . . secondary secondary . . . tertiary What class does the orbital shown belong to? Each dot represents a nucleus, and the signs of the wave function are shown. + A. σ 15. B. π C. p D. sp3 Which of the following compounds is NOT an isomer of the others? A. H2 C=CHCH 2 CH3 B. (CH3 )2 CHCH 3 C. 16. What functional groups is/are present in the molecule shown? A. B. C. D. Ester only Carboxylic acid and ether Ketone and ether Aldehyde only O || CH3 CCH2 OCH 3 31 D. CH3 17. Which of the following is NEITHER a cis isomer NOR a trans isomer? F F \ / A. C=C / \ H H 18. H Cl \ / B. C=C / \ Cl H H Br \ / C. C=C / \ H Br H H \ / D. C=C / \ I I What is the SHORTEST carbon-carbon bond in the molecule shown? H-C≡C-CH=CH-CH2 -CH3 A B C D 19. What is the formal charge on the oxygen atom in the structure shown? CH3 | .. .. CH3 —C—N—O: | .. .. CH3 A. +2 B. +1 C. 0 D. -1 20. What is the definition of a Lewis base? A. B. C. D. 21. Proton acceptor Proton donor Electron pair acceptor Electron pair donor Which of the compounds shown has the LOWEST boiling point? A. CH2 —CH2 | | OH OH B. CH3 CH2 | OH C. CH2 —CH2 | | CH3 CH3 32 D. CH 3 CH2 | CH3 22. What is the IUPAC name of the compound shown? CH3 A. B. C. D. 23. 9-methylbicyclo[4.3.0]nonane 7-methylbicyclo[4.3.0]nonane 2-methylbicyclo[4.3.0]nonane 1-methylbicyclo[4.3.0]nonane How many secondary amines are there with the formula C4 H11 N? A. 2 24. B. 3 C. 4 Which of the formulas shown represents a compound that is different from all the others? CH3 | A. CH3 CH2 CHCH 2 Cl C. 25. D. 5 Cl CH2 Cl | B. CH3 CHCH 2 CH3 D. Cl Which of the compounds shown can form hydrogen bonds with other molecules of the same kind? O || I. (CH3 )2 NH II. N-CH 3 III. CH3 C-OH IV. CH3 OCH 2 CH2 OCH 3 A. II and III only B. I and III only C. I and IV only 33 D. I, II, and III