1.What type of reaction is the following? NaOH B)substitution C)addition D)rearrangement E) Ans: 2.What would be the major organic product of the following reaction? CH3 H HCI H;C-C-C CH:CH A HC H H:C-C -C-CH2CI HC H HC CI H:C-C-C-CH; HaC H c) CI H H;C-C-C-CH3 HC CHs D) H;C-C-C-CH3 HC H E) HC CI CI H:C-C-C-CH Ans:C
Page 1 1. What type of reaction is the following? Cl NaOH A) elimination B) substitution C) addition D) rearrangement E) reduction Ans: A 2. What would be the major organic product of the following reaction? CH3 C CH3 H3C C CH2 H ? HCl A) H3C C H3C H3C C CH2Cl H H B) H3C C H3C H3C C CH3 Cl H C) Cl C H3C H3C C CH3 H CH3 D) H2C C H3C H3C C CH3 H H Cl E) H3C C H3C H3C C CH2 Cl Cl H Ans: C
3.What would be the majororganic product of the following reaction? H:C-CH2-CH2 cCH,0,HS04→ 2 CH3 A) HC-CH-CH2_CH2-OH CH3 H:C-CH2-CH2_OHCH CHa C) H,C-CH-CH,月cH-0oH HC-CH2-CH2、 00H CH3 H,C-C-CH、8 H Ans:B Page2
Page 2 3. What would be the major organic product of the following reaction? H3C CH2 CH2 C CH2 CH3 H2O, H2SO4 ? A) H3C CH2 CH2 C CH2 CH3 H OH B) H3C CH2 CH2 C CH3 CH3 OH C) H3C CH2 CH2 C CH2 CH3 OOH H D) H3C CH2 CH2 C CH3 CH3 OOH E) H3C CH2 CH2 C C CH3 O H H Ans: B
4.Reaction with oone,followed by treatment with(CHS.of which ofthe following would not yield any CH3CHO? H CC=C H CH3 H、H Cc=c H;C CH; C) HC、 CH3 H =c CH; H HC H hs o :and D I-methyleyclohevenen CH3 OH A)1.CH;CO3H CH;ONa,CH;OH KM 1.Os0 2.H2S.H20 E) 1.05 Ans: Page3
Page 3 4. Reaction with ozone, followed by treatment with (CH3)2S, of which of the following would not yield any CH3CHO? A) C C H CH3 CH3 H B) C C H CH3 H H3C C) C C H3C CH3 CH3 H D) C C H H CH3 H3C E) Both B and D Ans: A 5. Which of the following sets of reagents would convert 1-methylcyclohexene into trans-1-methyl-1,2-cyclohexanediol? CH3 OH ? CH3 OH A) 1. CH3CO3H 2. CH3ONa, CH3OH B) KMnO4, H2O, -OH C) 1. CH3CO3H 2. H3O+ D) 1. OsO4 2. H2S, H2O E) 1. O3 2. (CH3)2S Ans: C
6.What reagent(s)would accomplish the following transformation .-CH2Br H:C CH2 HC-CH B)HB r C)PBr3 D)HBr+peroxides E)HgBr2+ Ans:D 7.Which of the reagents below would best accomplish the following transformation? OH Ans:+O Page 4
Page 4 6. What reagent(s) would accomplish the following transformation? CH2 H3C CH2 C CH2 H3C CH2 H3C CH CH2Br H3C CH2 ? A) Br2, hν B) HBr C) PBr3 D) HBr + peroxides E) HgBr2 + NaBH4 Ans: D 7. Which of the reagents below would best accomplish the following transformation? OH ? OH A) H2O + cat. H2SO4 D) O3 then Zn + HCl B) CH3CO3H, then NaOH + H2O E) KMnO4 + - OH/ H2O C) Br2 + H2O Ans: E
8.What would be the product of the following reaction? H:CH Br H:C CH Br Br 9 Br、H B跃BH E) Ans:D 9.Which of the following reagents would best accomplish the following transformation? CH: ◇CH A)NaBH4 B)LiAIH4 C)BH3,NaBH4 D)H2SO4 E)H2,Pd Ans:E Page5
Page 5 8. What would be the product of the following reaction? H3C H H CH3 Br2 ? A) H3C Br CH3 H B) H3C CH3 H H Br Br (racemic) C) H3C H CH3 Br D) H3C H CH3 H Br Br E) H3C H CH2Br H Ans: D 9. Which of the following reagents would best accomplish the following transformation? CH3 CH3 ? A) NaBH4 B) LiAlH4 C) BH3, NaBH4 D) H2SO4 E) H2, Pd Ans: E
10. large mo stable tha the E alkenes are too unstable to store Ans:C 11.Radical polymerization of styrene produces what polymer?(n=large number) heat o犬代x w入 ofx Page6
Page 6 10. Polymerization reactions are thermodynamically favorable (exothermic) because A) large molecules are more stable than small ones. B) polymers precipitate, which shifts the equilibrium. C) a sigma bond is more stable than a π bond. D) crosslinking stabilizes the product. E) alkenes are too unstable to store. Ans: C 11. Radical polymerization of styrene produces what polymer? (n = large number) Ph ? heat cat. R-O-O-R A) RO Ph Ph Ph n B) RO Ph Ph Ph n C) RO Ph Ph Ph Ph Ph Ph n D) RO Ph Ph n E) none of the above Ans: B
12.What would be the expected product of the following reaction? L ArCO-H 2.H20,Na0H C Page7
Page 7 12. What would be the expected product of the following reaction? ? 1. ArCO3H 2. H2O, NaOH A) OH HO B) OH HO C) H HO D) OH H E) OH H Ans: B
13.Basedon your mechanisms invovd which of the r elow CH2Br B)Br2 C)PBr3 D)NaBr E)HBr+peroxides 14.What type of reaction is the following? h NC-CN D)rearrangement E) Ans:C Page 8
Page 8 13. Based on your knowledge of the mechanisms involved, which of the reagents below would you expect to accomplish the following reaction? (Think through the mechanism!) OH O CH2Br ? A) HBr B) Br2 C) PBr3 D) NaBr E) HBr + peroxides Ans: B 14. What type of reaction is the following? Br CN NaCN A) elimination B) addition C) substitution D) rearrangement E) reduction Ans: C
15.Which of the following rearrangements would you not expect the cation below to undergo to any significant extent? H,C、CH-CH H,C、CH B CH3 CH2-CH2 C) CH3 D)None of the above would occur to a significant extent E)All of the above would be significant. Ans:B Page9
Page 9 15. Which of the following rearrangements would you not expect the cation below to undergo to any significant extent? H3C CH CH3 ? + A) H3C C CH3 H + B) CH3 CH2 CH2 + C) CH3 CH3 + D) None of the above would occur to a significant extent. E) All of the above would be significant. Ans: B
6.What is the major product of the following reaction? heat Page 10
Page 10 16. What is the major product of the following reaction? HBr /cat. R2O2 heat ? A) B) Br C) Br D) Br Br E) CH2Br Ans: C