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MC Ho
MC Ho
1. Which one of the following would not be a suitable solvent for Grignard reagents?
7.
CH3(CH2)3CH2Br
1) 4-nonene
1) CH3 CH2 OCH2 CH3 , diethyl ether 2) CH3 CH2 OH, ethanol 3) O 4) they would all be suitable solvents
CH3CH2C
2) nonane
3) 4-bromononane
4) 5-bromononane
, tetrahydrofuran (THF)
8.
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
OH 1) OH 2) OH 3) OH 4)
9.
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
10.
PBr3
OH 3)
PBr3
NaOD, D 2O
1)
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)
OH
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
OD 3) CH3CH2CCH3 H
2) CH3CH2CCH3 D
12. 5. Reaction of excess Grignard reagent with diethyl carbonate, shown below, gives a(n): O
EtO C OEt
1) ketone
2) tertiary alcohol
3) secondary alcohol
4) ester
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)
3) 3-bromopentane
1) CH3CH=O 2) H
+
13.
OH
NaBH4 CH3 OH
HBr
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.
18.
15.
Which compound below is the product expected from the following reaction?
O H3C O CCH 3 O H 1) LiAlH4 , diethyl ether 2) H2O
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
HO OH R
O
+ H2O R'
O 4) CH3 CCCl3
HO 2)
CH3 OH 4)
H3C
CH2OH H O
1) CH3 CCH3
3) CH3CCHCl2
21.
Which compound below fits the following proton NMR data? triplet 1.22 (3H) singlet 1.98 (3H) quartet 4.07 (2H)
O 1) CH3 CH2COCH3 3) H2 C=C CH3 OCH3
16.
18-crown-6
O 4) CH 3CCH2OCH 3
1) complex F- by ion-dipole attraction and make it more nucleophilic. 2) remove Br- by ion-dipole attraction and shift the equilibrium to the products. 3) complex K+ by ion-dipole attraction increasing the solubility of KF and the nucleophilicity of F-. 4) stabilize the carbocation in the substitution reaction. 17. What are the products of the reaction below?
OH HI (xs), heat
22.
Which one of the following works best as the reaction steps to carry out the conversion below?
CH CH2 ? CH 2 CHO
CH2 OCH3
23.
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 of the following have an enol form? A benzaldehyde, C6H5CHO B. 2,2-dimethylpropanal, (CH3)3CCHO C. 2,2-dichloropropanal, CH3CCl2CHO 1) none have enol forms 2) only A 3) only B 4) A and C
29.
24.
OH
2) (E)-3-penten-2-one 4) (E)-3-pentenal
CH2 CH3
3) 6-hydroxy-3-heptanone 4) 6-hydroxyheptanal
H O
O
HOCH 2CH 2OH, 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.
Identify the starting reagents needed to make the following compound by a mixed aldol condensation. O KOH, CH3 OH ? CH=CCCH2CH3
CH3
26.
Which one of the following gives ethanal, CH3CH=O, (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, shown above, with no formation of isomeric by-products?
Which of the following is the strongest acid? 1) FCH2CO2H 2) ClCH2CO2H 3) BrCH2CO2H 4) ICH2CO2H
OH 1)
H2SO4 heat
34.
2)
OH
H2 SO4 heat
1) (CH3)2CHCH2CH2NH2
Cl 3) (CH3)3CO Na
+
2) (CH3)2 C=CHCO2H
O 4) H2 C=P(C6 H5 )3
35.
40.
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. 36. 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
Which of the following is the product of the reaction sequence shown below?
O (1) NaOEt (1) NaOH, H2O, heat (2) H3 O
+
37.
heat
OEt (2) H O+ 3
1) 4-methyl-3-hexanone 2) 4-heptanone 3) propanal and HCl 4) methyl propanoate and HCl 43.
The acetoacetic ester synthesis, shown below, can be used to prepare 5-methyl2-hexanone. Which one of the following alkyl bromides would be used in the synthesis?
O O (1) NaOEt (1) NaOH, H2O
+
pyridine
heat
5-methyl-2-hexanon
O 1) O
HO H 3)
O H3 C H O
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.
Which of the following is the Claisen condensation product of ethyl propanoate, CH3CH2CO2Et?
O 1) O OEt 3) O O OEt
45.
To convert a nitrile to a primary amine you must: 1) hydrolyze it with water. 2) oxidize it with chromic acid. 3) reduce it with hydrogen or lithium aluminum hydride. 4) substitute it with an alkyl halide.
46.
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