PRACTICE FIRST HOUR EXAM B 1. Which of the following bond angles is the LARGEST? A. B. C. D. 2. H—O—H in H2 O H—C—O in CH 3 OH C—C—O in CH2 =CH-OH C—O—C in CH 3 OCH 3 A compound with the formula C4 H8 O can belong to any of the following families of organic compounds EXCEPT which one? A. ketone 3. ORGANIC CHEMISTRY 2210 B. carboxylic acid C. ether Which of the following compounds contains the MOST secondary hydrogen atoms? A. D. What is the relationship between the structures shown? and A. B. C. D. 5. CH3 | CHCH 2 CH3 B. CH(CH 3 )2 C. 4. D. alcohol (CH3 )3 C(CH2 )3 CH(CH 3 )2 Different compounds that are isomers Different compounds that are not isomers The same compound Resonance structures Which of the following compounds has the highest boiling point? A. CH3 CH2 CH2 OCH 3 B. CH3 CH2 CH2 CH3 C. CH3 —N—CH 3 D. | CH3 34 CH3 CH2 CH2 —N—H | CH3 6. What is the name of the compound shown? CH2 CH(CH 3 )2 A. B. C. D. 7. 7-tert-butylbicyclo[3.2.1]octane 6-isobutylbicyclo[3.2.1]octane 3-isobutylbicyclo[3.2.1]octane 2-tert-butylbicyclo[3.2.1]octane What type of orbital is occupied by the nonbonding electron pairs in the molecule shown? :O: || H—C—H A. sp2 8. B. sp3 C. s D. p What functional groups are present in the molecule shown? O O N O A. B. C. D. 9. C-OH || O Ester, amide, carboxylic acid Amine, ketone, ester, carboxylic acid Amide, ether, carboxylic acid, ketone Ether, amide, carboxylic acid In the structure shown, what are the formal charges on the nitrogen atom and the starred oxygen atom, respectively? .. :O: CH3 —N A. +1, 0 ..O: B. +1, -1 * C. 0, 0 D. 0, -1 35 10. Which of the compounds shown is the most soluble in water? A. 11. C. O D. In the dinitramide ion (shown below without charges), what are the shape and approximate bond angles of the portion of the molecule around the indicated atom? :O: :O: .. | | .. | | .. :O—N—N—N—O: .. .. .. A. B. C. D. 12. Cl B. Trigonal planar, 120˚ Trigonal pyramid, 120˚ Trigonal planar, 109.5˚ Trigonal pyramid, 109.5˚ The IR spectrum of the compound shown contains a peak in which of the following regions? OH A. B. C. D. 13. 1620-1680 cm-1 2100-2260 cm-1 3200-3550 cm-1 2220-2260 cm-1 Which of these is a pair of isomers? H H A. H CH3 CH3 and H CH3 CH3 C. B. H H CH3 CH3 CH3 CH3 H3 C H D. H H H CH3 CH3 H H3 C CH3 H and H H CH3 36 H and H H and H H H H H 14. What is the structure of 2,2-dimethylcycloheptanol? B. A. OH 15. D. C. OH OH OH In the reaction shown, _____ is the conjugate _____ of CH3 OH. KH + CH3 OH ------> H2 + CH3 OK A. B. C. D. 16. H2 . . . acid H2 . . . base CH3 OK . . . acid CH 3 OK . . . base Which of the following compounds is a 3˚ alkyl halide? H H A. B. CH3 17. H Br D. (CH3 )3 CCH2 Br C. Cl Cl Which of the following compounds is both an ether and a ketone? A. O || B. O || C. O || O D. O 18. What is the IUPAC name of the compound shown? (CH3 )3 CCH2 CH2 CH2 CHOHCH(CH3 )2 A. B. C. D. 6-tert-butyl-2-methyl-3-hexanol 4-tert-butyl-1-isopropyl-1-butanol 2,2,7-trimethyl-6-octanol 2,7,7-trimethyl-3-octanol 37 O 19. Which of the following compounds is cis? H H A. Br B. CH3 20. H Br H Br C. CH3 H H Br CH3 Br D. CH3 H What is the IUPAC name of the compound shown? OH A. B. C. D. 21. Which of the following compounds is bicyclo[3.2.0]heptane? A. 22. 2-Methyl-4-butanol 2-methylbutanol 3-methyl-1-butanol 3-methylbutanol B. C. D. Which of the following compounds is neopentylcyclopentane? A. CH2 C(CH3 )3 C. CH2 CH3 | C(CH3 )2 B. CH2 CH2 CH(CH 3 )2 D. CH3 | CHCH 2 CH2 CH3 38 23. What is the IUPAC name of the compound shown? CH2 CH3 | CH3 CHCHCH 2 CH2 CH3 | OH A. B. C. D. 24. 3-methyl-4-heptanol 2-ethyl-3-hexanol 5-ethyl-4-hexanol 5-methyl-4-heptanol What are the hybridizations of atoms 1 and 2, respectively? 1 2 N—CH 2 —CH=C=O A. sp, sp2 25. B. sp, sp3 C. sp2 , sp2 D. sp 2 , sp3 What kind of orbital is the one illustrated? Nuclei are indicated by solid dots, and the signs of the wave functions are shown. + A. sigma (σ) atomic B. sigma (σ) molecular C. hybrid atomic D. hybrid molecular 39