Organic Chemistry 234 Sample Multiple-Choice Questions

1. Which one of the following would not be a suitable solvent for Grignard reagents?

7.

What is the product of the reaction shown below?

CH3CH2CH2CH2Br Li, 0 C diethyl ether
o

CuI, -20 C THF

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.

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)

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.

What is the product of the following reaction?

O (1) LiAlH4 (2) H2 O

PBr3

(1) Mg, diethyl ether (2) D 2O

O

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

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
+

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
+

O 4) 1-bromobutane Mg diethyl ether 1) CH3CCH3 2) H

+

13.

What is the product of the synthetic sequence below?

OH

NaBH4 CH3 OH

HBr

1) Mg, 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.

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 following reaction?

O H CH 3 NaOH, H2O

O 1) CH3 CH2COCCH3 O 2) CH3 COCH2 CH2 CH3

O 3) CH3CH2CH2CCH3 O 4) CH 3CH 2COCH 2CH 3

1) (S)-1,2-propanediol 2) (R)-1,2-propanediol 19.

3) racemic mixture of 1,2-propanediol 4) 1,3-propanediol

What is the IUPAC name of the following compound?

O

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

1) 3-methyl-5-heptanone 2) 5-ethyl-3-hexanone 20.

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

+ 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.

The role of 18-crown-6 in the reaction shown below is to:

CH3CH2CH2CH2 Br + KF 18-crown-6 C6 H6, 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- 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

1) (1) Br2 2) (1) B2H6/diglyme 3) (1) H2O, H2 SO4

(2) NaNH2(xs) (2) H2 O2, NaOH (2) CrO3 /H2 SO4

(3) H2 O, HgSO4/H2SO4 (3) PCC/CH2Cl2

CH2 OCH3

O 4) (1) CH3COOH (2) NaOH, H2O

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.

Identify the keto form of the following enol.

24.

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.

3) 6-hydroxy-3-heptanone 4) 6-hydroxyheptanal

H O

KOH, CH3 OH H heat

What is the product of the reaction shown?

O Br

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?

1) 4-hydroxy-3-methylbutanoic acid 2) 3-hydroxy-2-methylbutanoic acid 33.

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.

What is the product of the following sequence of reactions?

(CH3 )2 CHCO2H (1) LiAlH4 (2) H2O PBr3 KCN DMSO H2 O, 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

35.

Which of the following is the product of the reaction sequence below?

CH3 NBS, CCl4 , heat benzoyl peroxide C(CH3 )3 (1) Mg/ether (2) CO2 H3 O
+

40.

What is the product of the reaction shown below?

O EtO O 1) NaOEt, 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. 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

1) ethyl 2-methylpentanoate 2) ethyl 4-methylpentanoate 42.

3) ethyl 3,3-dimethylbutanoate 4) ethyl 5-methylhexanoate

Which of the following is the product of the reaction sequence shown below?
O (1) NaOEt (1) NaOH, H2O, heat (2) H3 O
+

37.

The following tetrahedral intermediate breaks down to:

OH CH 3CH2 C Cl OCH 3

heat

OEt (2) H O+ 3

1) 4-methyl-3-hexanone 2) 4-heptanone 3) propanal and HCl 4) methyl propanoate and HCl 43.

3) 2-propylbutanoic acid 4) 2-ethylpentanoic acid

1) propanoyl chloride and CH3 OH 2) propanoic acid and CH3 Cl 38.

Which of the following is the product of the reaction shown below?

O H3 C C Cl + H OH

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

OEt (2) alkyl bromide ? (2) H3O

O 1) O

HO H 3)

O H3 C H O

1) (CH3)2CHBr CH3CH2CHBrCH3 44.

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