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1. Which one of the following would not be a suitable solvent for Grignard reagents?
What is the product of the reaction shown below?
CH3CH2CH2CH2Br Li, 0 C diethyl ether
CuI, -20 C THF
1) CH3 CH2 OCH2 CH3 , diethyl ether 2) CH3 CH2 OH, ethanol 3) O 4) they would all be suitable solvents
, tetrahydrofuran (THF)
What is the product of the following sequence of reactions?
CH (1) NaNH2, NH3 (2) CH3CH2Br H2 Lindlar Pd CH2I2 Zn(Cu)
2. Which of the following reaction sequences would convert 2-butanol into the deuterated compound below?
CH 3CH 2CHCH3 D
1) 1,1-diethylcyclopropane 2) trans-1,2-diethylcyclopropane
3) cis-1,2-diethylcyclopropane 4) cis and trans-1,1-diiodo-2,3diethylcyclopropane
OH 1) OH 2) OH 3) OH 4)
H2 SO 4 heat H2 SO 4 heat (1) BD3 /THF (2) H2O 2 , NaOH D2 /Pt
Which of the following cannot be made by the reduction of a ketone or aldehyde with NaBH4 in methanol? 1) 1-butanol 3) 2-methyl-1-propanol 2) 2-butanol 4) 2-methyl-2-propanol
What is the product of the following reaction?
O (1) LiAlH4 (2) H2 O
(1) Mg, diethyl ether (2) D 2O
NaOD, D 2O
3. The reaction of phenylmagnesium bromide (C6H5MgBr) with propanal (CH3CH2CH=O), followed by hydrolysis yields: 1) 2-phenyl-1-propanol 2) 1-phenyl-1-propanol 3) 2-phenyl-2-propanol 4) 3-phenyl-1-propanol 11.
OH 2) 4)
Give the product of the following reaction.
O (1) LiAlD4 (2) H2 O OH
4. Which of the following pairs of reagents would you use to prepare 4-methyl-2pentanol?
O 1) (CH3)2CHCH2Li + CH3 CH O 2) (CH3)2CHLi + CH3CCH3 4) CH3CH2 Li + 3) (CH3)2 CHLi + O CH3 CH2 CH O (CH3)2CHCH
OH 1) CH3 CH2 CCH3 H
OD 3) CH3CH2CCH3 H
OD 4) CH3 CH2 CCH3 D
2) CH3CH2CCH3 D
12. 5. Reaction of excess Grignard reagent with diethyl carbonate, shown below, gives a(n): O
EtO C OEt
Which of the following syntheses gives 3-methyl-1-hexanol?
O 1) 2-bromopentane Mg diethyl ether 1) 2) H
2) tertiary alcohol
3) secondary alcohol
2) 2-bromohexane Mg diethyl ether Mg diethyl ether 1) H2 C=O 2) H
6. Which of the reaction schemes below gives 1,4-pentadien-3-ol, H2C=CHCH(OH)CH=CH 2 as the major organic product and with minimal byproduct formation?
1) H2C=CHCHCH=CH2 + Br O 2) 2 H2C=CHMgBr + HCOCH2 CH3 followed by neutralization O 3) H2C=CHMgBr + H2C=CHCOH O 4) H2C=CHMgBr (xs) + CH3 CH3 OCOCH2 CH3 followed by neutralization H2 O (solvolysis)
1) CH3CH=O 2) H
O 4) 1-bromobutane Mg diethyl ether 1) CH3CCH3 2) H
H2O O 1) CH3 CH2COCCH3 O 2) CH3 COCH2 CH2 CH3 O 3) CH3CH2CH2CCH3 O 4) CH 3CH 2COCH 2CH 3 1) (S)-1. 3) racemic mixture of 1. 2) remove Br.by ion-dipole attraction and shift the equilibrium to the products. Which compound below fits the following proton NMR data? triplet δ 1. NaOH (2) CrO3 /H2 SO4 (3) H2 O. Et2O 2) H2C=O 3) H3O + PCC CH2Cl2 1) CH2 I OH + CH3OH 3) CH2 I I + CH3I OH 1) CO 2H 2) CHO 3) CHO 4) CH3 OH 2) + CH3I CH2 OH 4) CH2 I + CH3 I 14. HgSO4/H2SO4 (3) PCC/CH2Cl2 CH2 OCH3 O 4) (1) CH3COOH (2) NaOH. 4) stabilize the carbocation in the substitution reaction. What is the product of the following reaction? O H CH 3 NaOH. The role of 18-crown-6 in the reaction shown below is to: CH3CH2CH2CH2 Br + KF 18-crown-6 C6 H6. What are the products of the reaction below? OH HI (xs).2-propanediol 2) (R)-1. H2O . What is the product of the reaction below? O CH 3COH + CH3 CH2 CH2 OH H2 SO 4 heat 18. What is the product of the synthetic sequence below? I OH O NaBH4 CH3 OH HBr 1) Mg. heat 22. Which one of the following works best as the reaction steps to carry out the conversion below? CH CH2 ? CH 2 CHO 1) (1) Br2 2) (1) B2H6/diglyme 3) (1) H2O. heat CH3 CH2 CH2 CH2 F + KBr O O O O O O 18-crown-6 O 3) CH3 COCH2 CH3 O 4) CH 3CCH2OCH 3 1) complex F.2-propanediol 19. Which compound below is the product expected from the following reaction? O H3C O CCH 3 O H 1) LiAlH4 .3-propanediol What is the IUPAC name of the following compound? O 15. H2 SO4 (2) NaNH2(xs) (2) H2 O2. 17.2-propanediol 4) 1. 3) 5-methyl-3-heptanone 4) 2-ethyl-4-hexanone Which of the following has the largest Keq for the formation of the hydrate (as shown below)? O K eq R' O 2) CH3CCH2Cl O H3C 1) O CCH3 OH 3) H3C OH OH O HO OH R O R + H2O R' O 4) CH3 CCCl3 HO 2) CH3 OH 4) H3C CH2OH H O 1) CH3 CCH3 3) CH3CCHCl2 21.07 (2H) O 1) CH3 CH2COCH3 3) H2 C=C CH3 OCH3 16.by ion-dipole attraction and make it more nucleophilic.98 (3H) quartet δ 4. 3) complex K+ by ion-dipole attraction increasing the solubility of KF and the nucleophilicity of F-. diethyl ether 2) H2O 1) 3-methyl-5-heptanone 2) 5-ethyl-3-hexanone 20.22 (3H) singlet δ 1.13.
23. Identify the keto form of the following enol. 24. CH3 OH ? CH=CCCH2CH3 CH3 26. CH3CCl2CHO 1) none have enol forms 2) only A 3) only B 4) A and C 29. CH3 OH H heat What is the product of the reaction shown? O Br O HOCH 2CH 2OH. 2. shown above. Which of the following have an enol form? A benzaldehyde. 3) 1-hydroxy-2-methylbutanoic acid 4) 3-(hydroxymethyl)butanoic acid Which of the following is the strongest acid? 1) FCH2CO2H 2) ClCH2CO2H 3) BrCH2CO2H 4) ICH2CO2H OH 1) H2SO4 heat 34. O KOH. (as one of two products) when added to an aqueous solution of HCl? CH3 1) O H 3) O H O CH3 1) benzaldehyde (C6H5CH=O) and 3-pentanone 2) benzaldehyde (C6H5CH=O) and 2-pentanone 3) acetophenone (methyl phenyl ketone) and 2-butanone 4) acetophenone (methyl phenyl ketone) and butanal 32. What is the IUPAC name of the following compound? O HO OH O 2) O CH3 OH 4) O CH3 H 27. Which of the following methods can be used to synthesize 2-methyl-1-hexene. What is the product of the reaction of butanal with excess methanol and catalytic sulfuric acid? O 1) CH3 CH2CHCH OCH3 3) CH3 CH2CH2CH2OCH3 4) CH3 CH2 CH2 CH(OCH3 )2 O 2) CH3 CH2 CH2 COCH3 28. Which one of the following gives ethanal. 3) 6-hydroxy-3-heptanone 4) 6-hydroxyheptanal H O KOH. The compound shown below is the cyclic hemiacetal of: H3C OH O OH 1) 1-penten-3-one 3) 2-pentanone 30. 2) (E)-3-penten-2-one 4) (E)-3-pentenal What is the product of the following intramolecular aldol condensation reaction? O CH2 CH3 1) 5-hydroxyheptanal 2) 5-hydroxy-2-heptanone 25.2-dimethylpropanal. H heat + 2) OH H2 SO4 heat 1) (CH3)2CHCH2CH2NH2 Cl 3) (CH3)3CO Na + 3) (CH3)2 CHCHBrCO2H 4) (CH3)2 CHCH2CO2H 2) (CH3)2 C=CHCO2H O 4) H2 C=P(C6 H5 )3 . CH3CH=O. with no formation of isomeric by-products? 1) 4-hydroxy-3-methylbutanoic acid 2) 3-hydroxy-2-methylbutanoic acid 33. What is the product of the following sequence of reactions? (CH3 )2 CHCO2H (1) LiAlH4 (2) H2O PBr3 KCN DMSO H2 O. C6H5CHO B.2-dichloropropanal. Identify the starting reagents needed to make the following compound by a mixed aldol condensation. C6 H6 p-toluenesulfonic acid heat O Br 3) Br O O 4) O O Br O 2) 3) CHO 4) CHO 1) O O 1) O Br 2) O 31. (CH3)3CCHO C. 2.
To convert a nitrile to a primary amine you must: 1) hydrolyze it with water. 3) 2-propylbutanoic acid 4) 2-ethylpentanoic acid 1) propanoyl chloride and CH3 OH 2) propanoic acid and CH3 Cl 38.35. The following tetrahedral intermediate breaks down to: OH CH 3CH2 C Cl OCH 3 heat 2 OEt (2) H O+ 3 1) 4-methyl-3-hexanone 2) 4-heptanone 3) propanal and HCl 4) methyl propanoate and HCl 43. shown below. 4) substitute it with an alkyl halide. heat (2) H3 O + 37.3-dimethylbutanoate 4) ethyl 5-methylhexanoate Which of the following is the product of the reaction sequence shown below? O (1) NaOEt (1) NaOH. H2O + pyridine heat 5-methyl-2-hexanon OEt (2) alkyl bromide ? (2) H3O O 1) O HO H 3) O H3 C H O 1) (CH3)2CHBr CH3CH2CHBrCH3 44. What is the product of the reaction shown below? O EtO O 1) NaOEt. 2) (CH3)2CHCH2Br 3) (CH3)2CHCH2CH2Br 4) What is an acceptable name of the following compound? CH3CH2CH2CH2NHCH3 1) N-methylbutylamine 2) 1-methyl-1-butylamine 3) N-butylmethylamine 4) 2-pentylamine O 2) O H OH 4) O O H CH3 39. H2O. 36. Which of the following is the product of the reaction shown below? O H3 C C Cl + H OH The acetoacetic ester synthesis. heat benzoyl peroxide C(CH3 )3 (1) Mg/ether (2) CO2 H3 O + 40. CH3CH2CO2Et? O 1) O OEt 3) O O OEt 45. 3) ethyl 3. 2) oxidize it with chromic acid. CCl4 . O 2) OEt O 4) OEt O Which pair of reagents would be used to make the following amine by reductive amination? H2 /Pd ? + ? CH3 CH2 CHCH2NHCH3 CH3 1) methylamine and 2-methylbutanoic acid 2) methylamine and 2-methylbutanal 3) ammonia and 3-methyl-2-pentanone 4) dimethylamine and 2-butanone . EtOH OEt 2) H + CH3 HO2 C 1) C(CH3)3 2) CO2 H 3) C(CH3)3 H3C CH3 4) C CH3 CH2CO2H O CH2CO2Et CO2Et CO2Et 2) 3) O CO2 Et 4) OH CO2 Et C(CH3)3 1) CH2 CO2H 41. 3) reduce it with hydrogen or lithium aluminum hydride. Which one of the following alkyl bromides would be used in the synthesis? O O (1) NaOEt (1) NaOH. Which of the following is the Claisen condensation product of ethyl propanoate. can be used to prepare 5-methyl2-hexanone. Which one of the following compounds undergoes decarboxylation upon heating? O 1) O OH 3) O O Which one of the following esters gives the Claisen condensation product shown below? O O OEt OH O 2) O OH 4) O O OH 1) ethyl 2-methylpentanoate 2) ethyl 4-methylpentanoate 42. 46. Which of the following is the product of the reaction sequence below? CH3 NBS.
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