Midterm 1 Questions

1. What is the change in oxidation state of the metal when lithium reacts with 1-chlorobutane to give CH3CH2CH2CH2Li? a. 0 → +2 b. 0 → +1 c. 0 → −1 d. 0 → −2 2. Which of the following cannot be used as solvent for the formation of phenyl lithium by the reaction of phenyl bromide with lithium? a. Tetrahydrofuran b. Pentane c. Ethanol d. Diethyl ether 3. Which of the following bonds has the most ionic character? a. C−Mg b. C−Cu c. C−Li d. C−Zn 4. Which of the following compounds is the strongest base? a. Na2CO3 b. methylamine c. MeOLi d. MeMgBr 5. What is the major organic product obtained from the following sequence of reactions? Mg HCl Br a. Chlorocyclopentane b. Cyclopentanol c. Cyclopentane d. Cyclopentylmagnesium bromide 6. Which of the following compounds is prepared by a reaction of an organolithium reagent with CuI? a. PhCuCl b. PhMgCl c. Ph2Zn d. (Ph)2CuLi 7. What is the major organic product obtained from the following reaction? Me 1234 O MgBr Ph HCl OH Me OH Ph 12345 1 Me 1232 OH OH Me I Ph Me Ph 4 3 a. 1 b. 2 c. 3 d. 4 Ph 8. Which of the following compounds is used as a replacement for diazomethane to generate methylene? a. CCl2 b. CH2 c. CBr2 d. IZnCH2I 9. What is the major organic product obtained from the following sequence of reaction?s I Li MeI CuI Ph Me Ph CuMe Ph 1 2 H Ph MeCu Ph 3 4 a. 1 b. 2 c. 3 d. 4 10. What is the major organic product obtained from the following reaction? Et Et CHBr3 (CH3)3COK Br Br 1 2 Et Br Br Br 3 a. 1 b. 2 4 c. 3 d. 4 11. What is the IUPAC name of the following compound? O Ph 21H 34 Me 2 phenyl a. 2-oxo-butylbenzene b. 2-phenylpentanal c. 2-propyl-2-phenylacetaldehyde d. 2-butylbenzene-2-carbaldehyde 12. What is the IUPAC name of the following compound? Me 6 O 5 43 I Me Me a. 6-methyloctan-3-one b. 3-oxo-6-methyloctanal c. 6-ethyl-3-oxo-3-octanal d. 6-ethyl-3-heptanone 13. What is the major organic product obtained from the following reaction? O Me Et MgBr Me Me OH Me HCl Me OH Et Me 1 Me Et O Me 3 Me Me 2 H Me Me Me II Me OH 4 a. 1 b. 2 c. 3 d. 4 14. What is the major organic product obtained from the reaction of acetaldehyde (CH3-C(O)H) with Grignard reagents? a. Primary alcohol b. Secondary alcohol c. Tertiary alcohol d. Primary, secondary or tertiary alcohol Rmgx a t 15. What is the major organic product obtained from the following reaction? O Me Me H 2O Li Ph H2SO4, HgSO4 OH O Ph Me Me 1O Et Ph x 2 OH Me O O Ph Me Ph O O x4 3 a. 1 b. 2 c. 3 d. 4 16. Which of the following compounds is best described as a cyanohydrin? a. PhCH2CH2CN b. PhCH2CH(CN)2 c. PhCH2CNHNH2 d. PhCH2CH(OH)CN 17. What is the major organic product obtained from the following reaction of a carbonyl compound? O Ph3P-CH-Et then H3O Et a. 1 b. 2 c. 3 d. 4 Me x 1 2 Et 3 4 x 18. Which combinations of alkyl halide and carbonyl compound can be used to prepare the following product by reaction of the Wittig reagent derived from an alkyl halide with a carbonyl compound? Br O 1 Br O 2 Br O Br 3 4 O a. only 1 and 3 b. only 1 and 2 c. only 2 and 4 d. only 1, 2 and 3 19. Which of the following compounds is an acetal? OMe Ph HO OH Me Ph OMe 1 2 HO OMe HO OMe Ph x Me Ph a. 1 b. 2 c. 3 d. 4 OH x 3 4 20. What is the major organic product obtained from the following reaction? O Me Ph EtOH H2SO4 OEt EtO OEt Me Ph Me 1 OEt Me a. 1 b. 2 c. 3 d. 4 O Ph 3 Ph 2 Me Ph 4 OEt x 21. Which of the following compounds is a hydrazone of benzaldehyde (PhC(O)H)? a. PhCH2N=NH b. PhCH=N=NH c. PhCH2-NH-NH2 d. PhCH=N-NH2 Ej 22. What is the major organic product obtained from the following reaction? H 3C O H 3C H CH3 N H H+ H 3C O H 3C N H 3C N(CH3)2 1 CH3 H 2 O H 3C H 3C H N(CH 3 )2 4 N(CH3)2 3 a. 1 b. 2 c. 3 d. 4 23. What is the major organic product obtained from the following reaction? O Zn(Hg), HCl heat Cl 1 2 OH 3 4 a. 1 b. 2 c. 3 d. 4 24. What is the major organic product obtained from the following reaction? O N 1 x Ph O Me Ph 3 MeOH Ph Me Ph a. 1 b. 2 c. 3 d. 4 NaBH3CN Me + PhNH2 Ph Ph Me Ph 2 x Ph HN Me Ph 4 25. What is the major organic product obtained from the following reaction? O HO 3 21 H NaBH4 a. propanedioic acid b. 3-oxopropanoic acid c. 3-hydroxypropanoic acid d. 1,3-propanediol 26. What is the major organic product of the reaction of acetophenone (PhC(O)Me) with I2 and CH3CO2H? a. Ph-C(O)-CH2OH Me t Ir t citscozH b. Ph-C(O)-CH2I c. Ph-C(O)-CH(OH)2 d. Ph-C(O)-CI3 27. What is the major organic product of the reaction of benzaldehyde (PhC(O)H) with Ag2O in ethanol? a. Ketone b. Alcohol c. Acetal d. Carboxylic acid EN IF IF 28. What is the IUPAC name of the following compound O 876543 a 1 OH a. 3-methyl-3-butyl-6-propylhexanoyl acid xb. 3,6-dimethyl-6-ethylheptanoic acid x c. 3-butyl-3,6-dimethyloctanoic acid d. 3-butyl-3,6-dimethylheptanoic acid 29. Which of the following is the most soluble in water? a. Hexane b. 1-Pentanol c. Methanoic acid d. Ethanoic acid x 30. Which of the following is the correct order of increasing acid strength? a. CCl3CO2H > CH3CO2H > FCH2CO2H b. ClCH2CO2H > BrCH2CO2H > FCH2CO2H c. Cl2CHCO2H > ClCH2CO2H > CH3CO2H d. CH3CO2H > ClCH2CO2H > CH3OH x 31. What is the major organic product obtained from the following reaction? 1. KCN 2. H3O+ Ph Br Ph CH2OH OH x 1 Ph Ph CN 2 O Ph OH OH CO2H 4 3 a. 1 b. 2 c. 3 d. 4 32. What is the major organic product obtained from the following reaction? CH2N2 Et2O Me Me HO2C Me Me Me MeO2C 2 Me Me NH2C Me Me HO2C Me HO2C 1 Me HO2C 3 4 a. 1 b. 2 c. 3 d. 4 33. What is the major organic product obtained from the following reaction? CH3OH H2SO4 O H 3C OH chloride xa.b. Ethanoyl Methyl ethanoate c. Ethanoic anhydride d. Ethanoic sulfide x 34. What is the major organic product obtained from the following reaction? 1. NaBH4 2. H3O+ O MeO 32I OH a. 3-Methoxypropionaldehyde b. 3-Methoxy-1-propanol c. Propane-1,3-diol d. 3-Methoxypropanoic acid It 35. Which of the following compounds is a lactam? O O O O NH O O N H N H 2 1 a. 1 b. 2 c. 3 d. 4 O x3 O x4 36. What is the IUPAC name of the following compound? O 432O I a. Phenyl propionate b. Propyl benzoate c. Benzyl propionic acid ester d. Ethyl benzoate 37. Which of the following is a secondary amide? a. CH3-C(O)N(CH3)2 b. CH3-C(O)NHC(CH3)3 c. H-C(O)N(CH3)2 d. CH3-C(O)NH2 38. Which of the following is the correct order of decreasing reactivity in nucleophilic acyl substitution reactions, that is from more reactive to less reactive? a. Amides, acid chlorides, anhydrides b. Esters, amides, acid chlorides c. Acid chlorides, anhydrides, amides d. Amides, esters, acid bromides RIER 39. What is the major organic product obtained from the following reaction? O CH3NH2 Br a. Amide b. Enamine c. Imine d. Hydrazone 40. What is the major organic product of the following sequence of reactions? CO2 then HCl Mg Br a. Anhydride b. Carboxylic acid c. Acid chloride d. Ester SOCl2 ringerYEE 41. What is the major organic product of the following reaction? O OCH3 1. DIBALH 2. H3O+ O H OH 1 2 O OH OH 4 3 a. 1 b. 2 c. 3 d. 4 42. What is the major organic product obtained from the reaction of ethyl formate (H-CO2Et) using excess of phenyl lithium? Heo ft a. Secondary alcohol b. Anhydride c. Tertiary alcohol d. Ketone x 43. What is the major organic product of the following reaction? HO 1. LiAlH4 2. H3O+ CN O HO OH x HO NH2 1 HO x 3 a. 1 b. 2 c. 3 d. 4 2 CN HO NH2 O 4 44. What is the major organic product of the following sequence of reactions? O Ph Me2CuLi SOCl2 H 2O Cl Me Me OH O Ph O Me Ph 1 O Ph 2 O O Ph O Ph Me 4 3 a. 1 b. 2 c. 3 d. 4 45. Which of the following compounds is an enol? O a. 1 b. 2 c. 3 d. 4 H O 1 2 OH O 3 4