1.Rank the following in order of decreasing basicity (most basic on left): CH CH3 B)Y>X>Z C)Z>Y>X D)X>Z>Y E) Ans:A Page1
Page 1 1. Rank the following in order of decreasing basicity (most basic on left): H3C N CH3 CH3 H3C N CH3 CH3 C O NH2 X Y Z A) Z > X > Y B) Y > X > Z C) Z > Y > X D) X > Z > Y E) X > Y > Z Ans: A
2.Which of the following sets of reagents would accomplish the reaction shown below? HgC-C-Br C-NH CHa CH 1.Na'N3 2.LiAlHa 3.H0 1 Na+CN 3.H20 c) NH3 D 1.Mg.ether 2.C02 3.H30 4.S0C2,？ 5.NH3 6.Br2.NaOH E) 1.N-Na 2.H2S04,H20, Ans:D Page2
Page 2 2. Which of the following sets of reagents would accomplish the reaction shown below? CH3 C CH3 H3C Br CH3 C CH3 H3C NH2 ? A) 1. Na+ N3 - 2. LiAlH4 3. H2O B) 1. Na+ -CN 2. LiAlH4 3. H2O C) NH3 D) 1. Mg, ether 2. CO2 3. H3O+ 4. SOCl2, ? 5. NH3 6. Br2, NaOH E) N O O - Na+ 1. 2. H2SO4, H2O, ? Ans: D
3.Which of the following products would you expect to result from the following eactions? H3C、NH CH;I(xs) Ag2O K2C03 heat 超 Page 3
Page 3 3. Which of the following products would you expect to result from the following reactions? H3C NH2 ? Ag2O H2O heat CH3I (xs) K2CO3 heat A) H3C NH(CH3) B) H3C N(CH3)2 C) H3C N(CH3)3 D) CH2 E) H3C Ans: D
4.What product would result from the following reaction? NH3,H2O 2 NaBH3CN DH2-3 A) 0 Ans:D 5.Which of the following represents N-ethyl-2-phenylethylamine? A) CH2CH2Ph CHCH2、NPh CHCH、 H Ph-CHCHa 一NH2 CH2CH Ans: Page4
Page 4 4. What product would result from the following reaction? O ? NH3, H2O NaBH3CN pH 2-3 A) NH D) NH2 B) OH E) NH2 C) HO CN Ans: D 5. Which of the following represents N-ethyl-2-phenylethylamine? A) CH3CH2 N H CH2CH2Ph B) CH3CH2 N Ph CH2CH3 C) CH3CH2 N H CH3CH2 D) CH3CH2 N H Ph CHCH3 E) NH2 CH2CH3 Ans: A
6.What would be formed in the following reaction? NH3 CH;I-? 1 mole 1 mole A)CH;NH2 B)(CH3)2NH C)(CH3)3N D)none of these E)all ofthese Ans:E Easily r Tend to be carcinogenic 01 E)Have acidic N-H hydrogens c) Ammonia-like odor Ans:B 8.What is the result of the reaction shown? NaNOz CH3 HCI A CH C) X品 X E) N Xno Ans:E Page5
Page 5 6. What would be formed in the following reaction? NH3 + CH3I ? 1 mole 1 mole A) CH3NH2 B) (CH3)2NH C) (CH3)3N D) none of these E) all of these Ans: E 7. N-nitrosoamines (called nitrosamines) have what outstanding characteristic? A) An intense fishy odor D) Easily rearrange B) Tend to be carcinogenic E) Have acidic N-H hydrogens C) Ammonia-like odor Ans: B 8. What is the result of the reaction shown? CH3 N H CH3 NaNO2 HCl ? A) CH3 NO2 B) CH3 C) CH3 NO D) CH3 OH E) CH3 N NO CH3 Ans: E
9.Predict the major organic produet of the following reaction Br2/KOH/H2O N NH ns 10.What by-product(s)would you expect to contaminate methyl amine prepared by the following reaction? 2NH3+CH;I CH3NH2 NH r A)(CH3)NH D)all of the above B)(CH3)N E)none of the above C)(CHs)4N'F Ans:D Page6
Page 6 9. Predict the major organic product of the following reaction. NH2 O Br2 / KOH / H2O ? A) N O O B) N O O Br C) N O O Br D) NH2 E) NH2 Ans: D 10. What by-product(s) would you expect to contaminate methyl amine prepared by the following reaction? 2 NH3 + CH3I CH3NH2 + NH4 + IA) (CH3)2NH D) all of the above B) (CH3)3N E) none of the above C) (CH3)4N+ I- Ans: D
11.Which of the following is not limited to the synthesis of primary amines(R-NHor Ar-NH2)(i.e.,which,if any,can be used to make 2 or 3 amines)? Reduction of nitro groups with Fe/HCI Ans:B 12.What product would result from the Hofmann elimination of the following quaternary ammonium hydroxide HC、+ heat CH CHa CH3 CH- Page7
Page 7 11. Which of the following is not limited to the synthesis of primary amines (R-NH2 or Ar-NH2) (i.e., which, if any, can be used to make 2° or 3° amines)? A) Gabriel synthesis B) Reduction of amides with LAH C) Hofmann rearrangement D) Reduction of nitriles with LAH E) Reduction of nitro groups with Fe/HCl Ans: B 12. What product would result from the Hofmann elimination of the following quaternary ammonium hydroxide? CH3 N H3C CH3 CH3 + ? - OH heat A) CH3 B) CH3 C) H2N CH3 D) CH2 E) Ans: D
13. estructure of lithium diisopropylamide(LDA)
Page 8 13. What is the structure of lithium diisopropylamide (LDA)? A) N O Li B) Li N O C) N N O Li Li D) N O Li E) N Li Ans: E
14.Which of the following isot formed as either an intermediate along the reaction pathway or as a final product for the Mannich reaction shown below 8*只 HCI/EtOH/Heat 8路 Ans C 15.What process accomplishes the following transformation? R-NH2 Gabriel synthesis Mannich reaction Hofmann rearrangement Hofmann elimination C)Reductive amination Ans:B
Page 9 14. Which of the following is not formed as either an intermediate along the reaction pathway or as a final product for the Mannich reaction shown below? O H H O N H + + HCl / EtOH / Heat ? A) H H N Cl B) OH C) H H N H Cl D) O N H + Cl E) O N H Cl Ans: C 15. What process accomplishes the following transformation? R C O NH2 ? R NH2 A) Gabriel synthesis D) Mannich reaction B) Hofmann rearrangement E) Hofmann elimination C) Reductive amination Ans: B
16.What reagent(s)would accomplish the following? H,0 1.CHaI.heat 2.Ag2O,heat Ans:B 17.What major product would you expect from the reaction shown? CH,=0 ◇N(CH 〔J D) (CH) E) Ans:C 18.Which of the molecules below is the strongest base? B)CHo C)(CHN Dg⊙ Page 10
Page 10 16. What reagent(s) would accomplish the following? R C O NH2 R CH2 NH2 ? A) Br2, NaOH, H2O D) P2O5 B) 1. LiAlH4 2. H2O E) excess NH3 C) 1. CH3I, heat 2. Ag2O, heat Ans: B 17. What major product would you expect from the reaction shown? O CH2=O (CH3)2NH HCl ? A) N CH3 CH3 B) O N(CH3)2 C) O CH2 N H CH3 CH3 Cl D) HO N(CH3)2 E) HOH2C N(CH3)2 Ans: C 18. Which of the molecules below is the strongest base? A) (CH3)2NH B) CH3O C) (CH2)2N D) Cl E) HO Ans: C