4. Which of the following reactive intermediates can best be described as both a nucleophile and an electrophile?
(A) Carbocations
(B) Carbanions
(C) Carbenes
(D) Free radicals
(E) Alkanes

5. Are the compounds shown below best described as? (A) Cis-trans isomers (B) Constitutional isomers (C) Not isomers (D) Geometrical isomers (E) None of the above

6. Which functional group below indicates the presence of two atoms connected by a triple bond? (A) Alkyne (B) Alkene (C) Nitrile (D) Ester (E) Both A and C

7. The structures below are: (A) Geometrical isomers (B) Conformational isomers (C) Constitutional isomers (D) Structural isomers (E) Both ( A )and ( D )

8. Which of the following reagents will react with propane to give 2-propanol? (A) H₂O/H₂SO₄ (B) MgOH (C) NaBH₄ (D) Br₂/H₂O (E) H₂O₂/Pt

9. Which of the following reagents can be used to prepare epoxide from alkenes? (A) MCPBA in methylene chloride (B) Peroxyformic acid in water (C) Formic acid in water (D) Peroxybenzoic acid in sodium hydroxide (E) Peracid in water

10. Which of the following best describes DDT? (A) A chlorocarbon used to decaffeinate coffee beans. (B) A polybrominated organic compound used as a herbicide. (C) A polychlorinated organic compound used as an insecticide. (D) Mixed alkyl halides used as an anesthetic. (E) Freon used as a foaming agent.

11. Sᴺ2 reactions usually proceed with: (A) Equal amounts of inversion and retention at the center undergoing substitution. (B) Slightly more inversion than retention at the center undergoing substitution. (C) Slightly more retention than inversion at the center undergoing substitution. (D) Complete inversion at the center undergoing substitution. (E) Complete retention at the center undergoing substitution.

12. Which of the following alkyl halides can produce only a single alkene product when treated with sodium methoxide? (A) 2-chloro-2-methylpentane. (B) 3-chloro-3-ethylpentane. (C) 3-chloro-2-methylpentane. (D) 2-chloro-4-methylpentane. (E) 2-chloro-3-ethylpentane.

13. What would be the reaction product(s) from the following E2 reaction? (A) (B) (C) (D) (E) No reaction

14. Which of the following compounds are chiral? (A) I only. (B) II and III. (C) III and IV. (D) I and IV. (E) V only.

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