Sample ACS Organic Chemistry Examination

1. What is the IUPAC name for this compound?

(A) 1-methyl-4-isopropyl-1-cyclohexen-3-one
(B) 1-methyl-4-isopropyl-3-ketocyclohexane
(C) 5-methyl-2-methylethyl-5-cyclohexenone
(D) 3-methyl-6-methylethyl-2-cyclohexenone

2. Which is the structure of (Z)-3,5-dimethyl-3-nonene?

(A) (B)

(C) (D)

3. In which of these Lewis structures would the sulfur be assigned a formal charge
of +1?

O
(A) (B)
O
CH3 S O
CH3 S O

O
(C) CH3 S Cl (D) CH3 S Cl
O

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 Sample ACS Organic Chemistry Examination

4. What is the major product of this reaction sequence?

NaNH2 CH3 Br H2 O, H2 SO4

CH3 C C H I final
II product
HgSO 4
O O
(A) (B)
CH3 CH2 C CH3 CH3 CH2 CH2 C H
OH
(D)
(C) CH3 CH CHCH 2 OH CH3 CH2 CHCH 3

5. Which is the strongest base?

(A) CH2 NH2 (B) NH2

NH2 NH2
(C) (D)

O2 N O2 N NO2

6. What are the hybridizations of the atoms marked I, II, III, and IV in the
molecule?

II O IV
CH2 C CH2 OH

I III

(A) I = sp2 II = sp2 III = sp3 IV = sp3

(B) I = sp2 II = sp3 III = sp2 IV = sp3
(C) I = sp3 II = sp2 III = sp3 IV = sp3
(D) I = sp II = sp3 III = sp IV = sp2

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 Sample ACS Organic Chemistry Examination

7. Which of these compounds are aromatic?

I II III
(A) I, II, and III (B) II and III only
(C) I and III only (D) II only

8. What is the order from most stable to least stable for these conformations of
propylene glycol?

OH OH OH
H OH HO H H H

H CH3 H CH3 H CH3

H H OH
I II III

(A) III > II > I (B) I > II > III

(C) I > III > II (D) II > III > I

9. Which diastereomer is most stable?

H OH
H H
CH3 H
CH(CH 3 )2 CH3 OH
CH(CH 3 )2
(A) H (B) H
CH3 H CH3 OH

H OH H
H
CH(CH 3 )2 CH(CH 3 )2
(C) H (D) H

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 Sample ACS Organic Chemistry Examination

10. Which of these structures best depicts the transition state for the reaction of CH3I
with CH3OK in CH3OH?
H H H H
(A) CH3 C I (B) KO C I
H H

H H
H
(C) CH3 O C I (D) OH3 C H C I
H H

11. Which structure corresponds to the predominant form of this molecule near pH 7?

O O
(A) (B)
CH3 CH C OH CH3 CH C O
NH3 NH2

(C) O (D) O
CH3 CH C O CH3 CH C OH
NH3 NH2

12. The absolute configuration of the two carbons atoms in this compound are?

C6 H 5 CH3
SCH3
C C
D
H OCH3

(A) R – left carbon R – right carbon

(B) S – left carbon S – right carbon
(C) S – left carbon R – right carbon
(D) R – left carbon S – right carbon

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 Sample ACS Organic Chemistry Examination

13. Which proton in this molecule would be the most acidic?

B O
CH2 CH2 C H D

OH A

14. What is the correct stereochemical description of the relationship between this
pair of molecules?
OH H CH 3

H
H HO H
CH3
(A) identical (B) constitutional isomers
(C) enantiomers (D) diastereomers

15. Which structure is consistent with the proton NMR spectrum?

(A) (CH3 )3 COH (B) CH3 CH2 CH2 CH2 OH

CH3 OH
(C) CH3 CHCH2 OH (D) CH3 CH2 CHCH 3

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 Sample ACS Organic Chemistry Examination

16. Which resonance form best explains the greater acidity of p-nitrophenol relative
to phenol?

O (B) O O OH
(A) (C) (D)

N N N N
O O O O O O O O

17. Which is the order from the strongest acid to the weakest acid for these species?

+ +
CH3 OH CH3 OH2 CH3 NH2 CH3 NH3
I II III IV

(A) II > IV > I > III

(B) III > I > IV > II
(C) III > IV > I > II
(D) II > I > IV > III

18. Which statement is true?

(A) Compounds with R stereocenters rotate plane-polarized light clockwise.

(B) For equal concentrations and equal path lengths, solutions of (+) and (-)
enantiomers rotate plane-polarized light equally, but in opposite
directions.
(C) Racemic mixtures can rotate plane-polarized light either clockwise or
counterclockwise.
(D) Meso compounds can rotate plane-polarized light either clockwise or
counterclockwise.

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 Sample ACS Organic Chemistry Examination

19. What is the correct stereochemical description for these two Fischer projections?

CH2 OH O
HO H CH
H OH HO H
HO H H OH
CH HO H
O CH2 OH

(A) identical (B) meso compounds

(C) diastereomers (D) enantiomers

20. Which could be true about a compound with the molecular formula C12H20? It
may contain

(A) two rings and a double bond

(B) a triple bond and two rings
(C) two triple bonds
(D) a double bond and a ring

21. If this alcohol is dehydrated, which alkene is likely to be formed in the largest
quantity?

CH 3
H2 SO4
CH3 C CH CH2 CH3
CH 3 OH

CH3 CH3
(A) CH3 C CH CHCH 3 (B) CH3 C C CH2 CH3
CH3 CH3

CH3 CH3
(C) CH3 C CH CH2 CH3 (D) CH3 CH C CHCH 3
CH 2 CH3

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 Sample ACS Organic Chemistry Examination

22. Which is the proper representation of the flow of electrons in this E2 elimination?

OTs
C2 H5 ONa
CH3 CH2 CHCH 3 CH3 CH CHCH 3 + NaOTs + C 2 H5 OH

- -
C2 H 5 O C2 H 5 O
H H
(A) CH3 CH CH CH3 (B) CH3 CH CH CH3
OT3 OT3

- OTs
(C) C2 H5 O (D) CH3 CH2 CH CH3
CH3 CH CH CH3
-
H OT3 CH3 CH CH CH3 + OTs

C2 H 5 O
- H

23. What is the product of this reaction?

O
CH3 OH
H2 SO4
CH2 CH3
OCH3 OH
(A) (B) CH2 CH3
OH

CH2 CH3 OCH3

OCH3 OH
(C) CH2 CH3 (D) OCH 3

OH CH2 CH3

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 Sample ACS Organic Chemistry Examination

24. Which would form a racemic mixture upon hydrogenation of the double bond
with H2/Pt?

(A) C6 H 5 CH C C6 H 5 (B) C6 H 5 CH CH C6 H5
CH3
C6 H 5
(C) C6 H 5 CH CH CH 3 (D)

25. Which reaction is best suited for the preparation of t-butyl ethyl ether?

CH3 CH2 OK (CH3 )3 COH

(A) (CH3 )3 CBr (B) CH3 CH2 MgBr

(CH3 )3 COK CH3 CH2 OH

(C) CH3 CH2 Br (D) (CH3 )3 CMgBr

26. What is the stereochemistry of nitrile produced in the reaction shown?

CH2 CH3 CN
NaCN
C CH3 CH2 CHCH 3
H OTs
CH3
(S)-isomer

(A) 1:1 mixture of (R)- and (S)-

(B) (R)-isomer only
(C) unequal mixture of (R)- and (S)- isomers
(D) (S)-isomer only
27. Which carbocation is the most stable?

CHCH3 CH2 CH2

(A) (B)
CH3 CH3

CH2 CH3 CH2 CH3

(C) (D)

CH2 CH3

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 Sample ACS Organic Chemistry Examination

28. What is the principle product of the reaction shown?

CH3 ONa
(CH3 )3 CBr
CH3 OH

(A) CH3 OC(CH 3 )3 (B) CH3 OCH3

CH3
(C) CH2 C(CH3 )2 (D) CH3 OCH2 CHCH 3

29. Which sequence of reagents would effect this conversion in highest yield?
Cl

CH2 CH2 CH3

CH3 CH2 CH2 Cl Cl2

(A)
AlCl3 FeCl3

Cl2 CH3 CH2 CH2 Cl

(B)
FeCl3 AlCl3
O
CH3 CH2 CCl Zn(Hg) Cl2
(C)
+
AlCl3 H2 O, H FeCl3
O
CH3 CH2 CCl Cl2 Zn(Hg)
(D)
+
AlCl3 FeCl3 H2 O, H

30. Identify possible product(s) of dehydrohalogenationof trans-1-brom-2-

methylcyclohexane.

KOH
Br H

H CH3

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 Sample ACS Organic Chemistry Examination

CH 3 CH3 CH3
(A) (B)
only
+

CH3 CH3 CH2

(C) (D)
only +

31. Which two compounds ionize with loss of bromide ion to form the same
carbocation?
Br
Br

1 2
Br

Br
3 4

(A) 1 and 2 (B) 2 and 3 (C) 1 and 4 (D) 3 and 4

32. Predict the product of the reaction shown?

1. B2 H6
CH3
2. H2 O2 , NaOH

CH3 H
(A) H (B) H
H CH3
OH OH

CH3 CH3
(C) H (D) H
OH OH
H OH

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 Sample ACS Organic Chemistry Examination

33. Which substituents would deactivate benzene toward electrophilic aromatic

substitutio0n reactions?

O CH3
G= C OH N CH3 OH
CH3
I II III

(A) I, II, III (B) I and II only (C) II only (D) I and III only

34. Which reaction sequence would accomplish the synthesis of this alcohol?
OH
CH3 CH2 CHCH3
O
HBr Mg 1. HCH
(A) CH3 CH2 CH 2 OH
+
ether 2. H2 O, H
1. CH3 MgBr 1. LiAlH4
(B) CH3 CH2 CH2 OH + +
2. H 2 O, H 2. H2 O, H
conc. H2 SO4 H2 O
(C) CH3 CH2 CH2 OH +
180Þ C H
PCC 1. CH3 MgBr
(D) CH3 CH2 CH2 OH +
2. H2 O, H

35. What is the structure of the compound that gives the following proton NMR and
infrared spectra?

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 Sample ACS Organic Chemistry Examination

CH3
(A) CH3 CH CHCH2 OH (B) CH2 C CH2 OH

O
(C) CH2 CH CH 2 OCH3 (D) CH3 OCH CHCH

36. Which is the major kinetic product produced in the reaction shown?

CH3
HCl

CH3 CH3
(A) (B) Cl

Cl
Cl
(C) CH3 (D) CH3

Cl

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 Sample ACS Organic Chemistry Examination

37. Reduction of a triple bond to an E (trans) double bond can be accomplished with
which set of reagents?

(A) Na, NH3

(B) H2, deactivated Pd
(C) NaBH4, methanol
(D) NaH, then H3O+

38. What is the expected product from this oxidation?

OH
KMnO4 H2 O
CH3 C CH2 CH2 CH2 CH2 CH2 OH +
NaOH H
CH 3

O O O O
(A) CH3 C CH 2 CH2 CH2 CH2 COH (B) CH3 C CH2 CH2 CH2 CH2 CH

OH O OH O
(C) CH3 C CH 2 CH2 CH2 CH2 COH (D) CH 3 C CH2 CH2 CH2 CH2 CH
CH3 CH3

39. What is the major product from this reaction?

1. Hg(OAc)2 , H2 O
CH3
2. NaBH4

CH3 CH3
(A) H (B) HO
H H
OH H
OH CH3
(C) H H
(D)
CH3 OH
OH H

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 Sample ACS Organic Chemistry Examination

40. Which position will be attacked most rapidly by the nitonium ion (NO2+) when the
compound undergoes notration with HNO3/H2SO4 ?

O a b c d

CH3 C CH3

(A) a (B) b (C) c (D) d

41. Which radical is the least stable?

CH2 CH 3 CH2 CH3

(A) (B)

CH2 CH3 CH2 CH3

(C) (D)

42. Which of these is not a step in the mechanism of the aldol condensation?
-
O O O
(A) HC CHR (B) HC CHR HC CH2 R
H
-
OH

- O
O O H OH
(C) (D) RCH CH HC CH2 R
HC CHCHCH 2 R -
O
R

43. Which description is most applicable to the mechanism of this reaction?

Cl OH
O2 N NaOH O2 N
+ NaCl

NO2 NO2

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 Sample ACS Organic Chemistry Examination

(A) It takes place in one step with no ionic intermediates.

(B) It takes place in two steps; elimination then addition.
(C) It takes place in two steps; addition then elimination
(D) It takes place in three steps and involves a carbocation intermediate.

44. Which is the product of the reaction shown?

CH2 OH
H O H
H CH3 OH
OH H
dry HCl
OH OH
H OH

CH2 OCH3 CH2 OCH3

H O H H O H
(A) H (B) H
OH H OCH3 H
OH OH CH3O OCH3
H OH H OCH3
CH2 OCH3 CH2 OH
H O H H O H
H (D) H
(C) OCH3 H OH H
CH3O OH OH OCH3
H OCH3 H OH
45. Which structure is consistent with this proton NMR spectrum?

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 Sample ACS Organic Chemistry Examination

46. Ozonolysis of which terpene would give equimolar amounts of these compounds?

O O O
HO
H H
O

(A) (B)
OH OH

(C) (D)
OH OH

47. Which reagent sequence will effect the transformation shown?

CH3
(CH3 )2 CHBr C
CH3

C4 H9 Li (C6 H5 )3 P O

1 2 3

(A) 1, 2, 3 (B) 1, 3, 2 (C) 2, 1, 3 (D) 2, 3, 1

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 Sample ACS Organic Chemistry Examination

48. Which compound would produce this IR spectrum?

O O
CH COH
(A) (B)

O O
CH3 COCH 3
(C) (D)

49. Which intermediate is involved in the mechanism of this base-promoted

hydrolysis?
O -
OH
C OCH2 CH3
H2 O

O O
- + + -
(A) C O CH2 CH3 (B) C OCH2 CH3

-
O OH
(C) C OCH2 CH3 (D) C OCH2 CH3
OH +

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 Sample ACS Organic Chemistry Examination

50. Which structure is consistent with this proton NMR spectrum?

51. Which sequence of reagents would best effect this transformation?

O O O
CH3 CCH2 COCH 3 CH3 CCH2 CH2 C6 H5
+
NaOCH3 C6 H5 CH2 Br H2 O, H
(A)

+
NaOH C6 H5 CH2 Br H2 O, H
(B)

LiAlH4 HBr C6 H5 Li
(C)
+
C6 H5 CH2 Br NaBH4 H2 O, H
(D)

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 Sample ACS Organic Chemistry Examination

52. Which structure is a reasonable intermediate in the acid-catalyzed hydrolysis of

ethyl acetate in dilute aqueous acid?

-
O OH
(A) CH3 C OCH2 CH3 (B) CH3 C OCH2 CH3
OH + OH2
+
O O
(C) CH3 C OCH2 CH3 (D) CH3 C +
H

53. What is the product of this Grignard reaction?

O
1. CH3 CH2 MgBr
O +
2. H2 O, H (neutralize)

HO CH2 CH3 CH3 CH2 CH2 CH3

(A) O (B) O

O OH
(C) CH3 CH2 CCH2 CH2 CH2 OH (D) CH3 CH2 CCH2 CH2 CH2 OH
CH2 CH3

54. Which structure is consistent with this 13C NMR spectrum?

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 Sample ACS Organic Chemistry Examination

55. What would be the product of this reaction?

O -
HO
CH3 CH2 CH2 CH
H2 O
O O
-
(A) CH3 CH2 CH2 CCHCH (B) CH3 CH2 CH2 CH2 OH + CH3 CH2 CH2 COO2
CH2 CH3

OH O OH O
(C) CH3 CH2 CH2 CHCHCH (D) CH3 CH2 CH2 CHCH2 CH2 CH2 CH
CH2 CH3

56. What is the major product of the reaction shown?

O O +
H
CH3 CH 2 CH + H2 NNHCNH 2

O O
N C NHNH2 N NH C NH2
(A) CH3 CH2 CH (B) CH3 CH2 CH

O O
N C NH2 H2 N N C NH2
(C) (D)
CH3 CH2 CH CH3 CH2CH
OH

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 Sample ACS Organic Chemistry Examination

57. Which reagent will accomplish the conversion shown?

O O

?
CH3

(A) CH3 I (B) CH 3 MgBr (C) CH3 Li (D) (CH3 )2 CuLi

58. Which is the main product that can be isolated from the reaction shown?

O
HOCH2 CH2 OH
TsOH, C6 H6 , heat

OH OCH2 CH2 OH

(A) OCH2 CH2 OH (B) OCH2 CH2 OH

O OH HO
(C) (D)
O OCH2 CH2 O

59. What is the productof this reduction?

CH 3 O
LiAlH4 H2 O
CH3 CH2 CH C NHCH 3
ether

CH3 CH3
(A) CH3 CH2 CHNHCH3 (B) CH3 CH2 CHCH 2 OH

CH3 CH3
(C) CH3 CH2 CHCH NCH3 (D) CH3 CH2 CHCH 2 NHCH 3

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 Sample ACS Organic Chemistry Examination

60. What is the order from most reactive to least reactive forthese esters towards
aqueous hydroxide?

O O O
CH3 C OC(CH 3 )3 CH3 C OCH3 CF3 C OCH3
1 2 3

(A) 3>2>1 (B) 1>2>3 (C) 3>1>2 (D) 2>3>1

61. What is the expected product from this reaction sequence?

O +
HOCH 2 CH2 OH NaC CCH3 H2 O, H
BrCH2 CH2 CH +
H

OH OH
(A) HOCH 2 CH2 OCH2 CH 2 CHC CCH 3 (B) BrCH2 CH2 CHC CCH3

O O
(C) CH3 C CCH2 CH2 CC CCH 3 (D) CH3 C CCH2 CH2 CH

62. Which reagents are best for carrying out this reaction?

O O OH O

OCH2 CH3 OCH2 CH3

+
(A) NaBH4 , then H3 O (B) Zn(Hg), conc. HCl

(C) LiAlH4 , ether,then aqueous workup (D) NH2 NH2 , KOH

63. Which two of these reaction sequences will effect this transformation?

HO OH
CH3 C C CH3 C C
H H
CH3 CH3

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 Sample ACS Organic Chemistry Examination

H2 OsO4
I
deactivated Pd H2O2

Na OsO4
II
liq. NH3 H2O2

H2 CH3 CO3 H H2 O
III
deactivated Pd NaOH

Na CH3 CO3 H H2 O
IV
liq. NH3 NaOH

(A) II and III (B) I and III (C) I and IV (D) II and IV

64. What is the product formed from this reaction?

O
C CH3 1. Cl2 , NaOH
+
2. H2 O, H

O O
C Cl C CH2 OH
(A) (B)
O O
C CH3 C OH
(C) (D)

Cl

65. Which is the correct representation of the polymer fromed by free-radical

polymerization of this monomer?

CH2 CH CH3

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 Sample ACS Organic Chemistry Examination

(A) CH2 CH CH CH2 (B) CH C CH C

CH3 CH3 CH3 CH3 n
n

(C) CH CH2 CH 2 CH (D) CH2 CH CH2 CH

CH3 CH3 CH3 CH3
n n

66. With which reagents can the ketone shown be prepared viaa Diels-Alder reaction?

O
O O
CH 2
(A) + (B) +
CH 2

O O
O O

(C) + (D) +

O O
67. Which would be the best method to prepare propyl amine uncontaminated with
dipropyl amine?
O

NK

NH 3 H2 O
(A) CH3 CH2 CH2 Br (B) CH3 CH2 CH2 Br O
NaOH

O
NaBH4 KCN H2
(C) CH3 CH2 CNH2 (D) CH3 CH2 CH2 Br
CH3 OH Pt

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 Sample ACS Organic Chemistry Examination

68. Which reaction sequence might be used to synthesize this compound?

CO2 H

NO2
Br

CH3
Br2 1. KMnO 4 , NaOH,  HNO 3
(A) +
FeBr3 2. H2 O, H H2 SO4

CH3
1. KMnO4 , NaOH,  Br2 HNO 3
(B) +
2. H2 O, H FeBr3 H2 SO4

NO 2
Br2 CH3 Cl 1. KMnO4 , NaOH, 
(C) +
FeBr3 AlCl3 2. H2 O, H

NO 2
CH 3 Cl 1. KMnO4 , NaOH,  Br2
(D) +
AlCl3 2. H2 O, H FeBr3

69. Which of these compounds will show two triplets (amongother signals) in their 1H
NMR spectra?
I ClCH2 CH2 CHCl2

II ClCH2 CH2 CH2 Cl

III Cl2 CHCH 2 CHCl2

(A) I, II, III
(B) I only
(C) I, III only
(D) II only

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 Sample ACS Organic Chemistry Examination

70. What monomers are needed to produce this polymer?

O O
CCH2 CH2 COCH2 CH2 O
n
O O
(A) HOCH 2 CH2 COH + HOCH 2 CH2 COH

O
(B) ClCH2 COCH 2 Cl + HOCH 2 CH2 COCH 2 CH2 OH

O O
(C) HOC COH + HOCH 2 CH2 CH2 CH2 OH

O O
(D) HOCCH 2 CH 2 COH + HOCH 2 CH2 OH

27