13. What compound has a significant m/z 70 in its mass spectrum?
(A) 2-butanol
(B) diethyl ether
(C) ( E )-2-pentene
(D) 1-pentanol
(E) octane

1.Which of the following choices represent(s) a pair of resonance forms? (A) both (a) and (b) (B) both (b) and (c) (C) both (a) and (c) (D) All of the above

2.Which sequence correctly ranks the following protons in order of increasing acidity? (A)1＜2＜3(B)2＜3＜1 (C)3＜1＜2(D)3＜2＜1 (E)2＜1＜3

3.Which of the following statements about π molecular orbitals is/are correct?(A) π molecular orbitals are cylindrically symmetric. (B)Most of the electron density in a π molecular orbital is centered above and below the internuclear axis. (C) When two atoms are connected by a double bond, both of these bonds are π bonds. (D) Both statements B and C are correct. (E) Statements A, B, and C are all correct.

4.Which of the following compounds is not a constitutional isomer of a compound with an empirical formula C3H7O and a formula mass of 118.164?(A)(B)(C)(D)(E)

5. Identify the correct IUPAC name for the following structure. (A) 3-s-Butyl-1-iodo-2-methylhexane (B) 1-lodo-2,4-dimethyl-3-propylhexane (C) 4-(2-1odo-1-methylethyl)-3-methyIheptane (D) 2,4-Dimethyl-1-iodo-3-propylhexane.

6.The structures below are _______. (A) not isomers (B) conformation isomers (C) structural isomers (D) cis-trans isomers (E) both B and D.

7. When pyridine is treated with a mixture of nitric and sulfuric acids, the major product is _____. (A) 2-nitropyridine (B) 3-nitropyridine (C) 4-nitropyridine (D) both A and C

8. Which sequence of steps below describes the best synthesis of 5-oxohexanoic acid starting with 1-methylcyclopentan-1-ol?(A) 1. Conc. KMnO4；2. Dry gaseous HBr； 3. Mg/ether； 4. CO2 (B) 1. Conc. KMnO4；2. CH3MgBr/ether； 3. H3O+ (C) 1. H2SO4 and heat； 2. O3； 3. (CH3)2S (D) 1. H2SO4 and heat； 2. Conc. KMnO4； 3. LiAlH4； 4. H3O+ (E) 1. H2SO4 and heat； 2. Conc. KMnO4；

9. What compound is produced when cyclohexene is treated with concentrated KMnO4?(A) adipic acid (B) benzoic acid (C) succinic acid (D) cyclohexacarboxylic acid (E) caproic acid

10. Which of the following represents the highest occupied molecular orbital for the conjugated pi system in the structure below? (A)(B)(C)(D)

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