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Sample Acs Final Exam
Sample Acs Final Exam
(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
(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
1
Sample ACS Organic Chemistry Examination
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
2
Sample ACS Organic Chemistry Examination
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 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
3
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
4
Sample ACS Organic Chemistry Examination
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
CH3 OH
(C) CH3 CHCH2 OH (D) CH3 CH2 CHCH 3
5
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
6
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
20. Which could be true about a compound with the molecular formula C12H20? It
may contain
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
7
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
O
CH3 OH
H2 SO4
CH2 CH3
OCH3 OH
(A) (B) CH2 CH3
OH
OCH3 OH
(C) CH2 CH3 (D) OCH 3
OH CH2 CH3
8
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?
CH2 CH3 CN
NaCN
C CH3 CH2 CHCH 3
H OTs
CH3
(S)-isomer
CH2 CH3
9
Sample ACS Organic Chemistry Examination
CH3
(C) CH2 C(CH3 )2 (D) CH3 OCH2 CHCH 3
29. Which sequence of reagents would effect this conversion in highest yield?
Cl
KOH
Br H
H CH3
10
Sample ACS Organic Chemistry Examination
CH 3 CH3 CH3
(A) (B)
only
+
31. Which two compounds ionize with loss of bromide ion to form the same
carbocation?
Br
Br
1 2
Br
Br
3 4
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
11
Sample ACS Organic Chemistry Examination
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?
12
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
13
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?
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
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
14
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) (B)
(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
NO2 NO2
15
Sample ACS Organic Chemistry Examination
16
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
CH3
(CH3 )2 CHBr C
CH3
C4 H9 Li (C6 H5 )3 P O
1 2 3
17
Sample ACS Organic Chemistry Examination
O O
CH COH
(A) (B)
O O
CH3 COCH 3
(C) (D)
O O
- + + -
(A) C O CH2 CH3 (B) C OCH2 CH3
-
O OH
(C) C OCH2 CH3 (D) C OCH2 CH3
OH +
18
Sample ACS Organic Chemistry Examination
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)
19
Sample ACS Organic Chemistry Examination
-
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
O
1. CH3 CH2 MgBr
O +
2. H2 O, H (neutralize)
(A) O (B) O
O OH
(C) CH3 CH2 CCH2 CH2 CH2 OH (D) CH3 CH2 CCH2 CH2 CH2 OH
CH2 CH3
20
Sample ACS Organic Chemistry Examination
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
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
21
Sample ACS Organic Chemistry Examination
O O
?
CH3
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
O OH HO
(C) (D)
O OCH2 CH2 O
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
22
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
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
+
(A) NaBH4 , then H3 O (B) Zn(Hg), conc. HCl
63. Which two of these reaction sequences will effect this transformation?
HO OH
CH3 C C CH3 C C
H H
CH3 CH3
23
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
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
CH2 CH CH3
24
Sample ACS Organic Chemistry Examination
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
25
Sample ACS Organic Chemistry Examination
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
26
Sample ACS Organic Chemistry Examination
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