D. 2. Which of the following pathways is the BEST for the synthesis of 2-butanol
from ethane? A. B. C. D. (CH. 3. CH. 2. ) 2. CuLi Cl. 2 light. KOH heat ether light.
FINAL EXAMINATION -- MAY, 2001 -- ORGANIC CHEMISTRY II, CHEM 2220 -- *A* 1.
2.
What is the structure of the compound having the formula C10 H14 and the following proton NMR spectrum data? δ 7.1 ppm, multiplet, 4 H δ 2.8 ppm, septet, 1 H δ 2.3 ppm, singlet, 3 H δ 1.2 ppm, doublet, 6 H
A.
B.
C.
D.
Which of the following pathways is the BEST for the synthesis of 2-butanol from ethane?
A. B.
3.
(CH3CH2)2CuLi Cl2
Cl2 light (CH3CH2)2CuLi
light
C.
Cl2 light
D.
Cl2 light
KOH heat Cl2 light
KOH heat
CH3COCH3 H3O+ ether ether + Mg CH3CHO H3O ether ether Mg
Which of the following functional groups is present in all polypeptides? A. Alcohol
B. Carboxylic acid
C. Amine
D. Amide
4.
What is the major product of the reaction shown? O
O
CH 3 - C
C-OCH 3
LiAlD 4
H3 O
?
O
A.
CH 3 - C
B.
CD2 OH
CH 3 -CH
CH2 OD
OD O
C.
CH 3 -CD
CD 2 OH
D.
OD
CH 3 - C
CHOCH 3
OH
5.
What is the major organic product of the reaction shown? O
?
O
+ O
O A.
B. O
O O
O
O O
D.
C.
O
O O
O O
6.
Which of the following bromides would ionize most rapidly to form a carbocation? Br
Br
A.
B. Br D.
C.
7.
What is the relationship between the structures shown?
CH3
OH
C H | CH3 A. B. C. D. 8.
Br
CH3
HO H
C | CH3
Same compound Enantiomers Diastereomers Structural isomers
What is(are) the major organic product(s) expected from the following reaction?
NBS peroxides
+
A.
Br +
Br B.
Br Br C.
Br
Br
Br D.
Br
+
9.
What is the major organic product expected from the following reaction?
CH2Cl AlCl3
CH2Cl + excess A.
Cl
B.
Cl
Cl C.
Cl CH2
CH2 D.
Cl 10.
Which of the following is an INTERMEDIATE in the following reaction?
CH3COOCH3 + 2 CH3MgBr
11.
ether H3O+
(CH3)3COH + CH3OH
A. CH3CH(OH)CH3
B. CH3COO MgBr
C. (CH3)2CO
D. CH3COO MgBr
What is the IUPAC name of the compound shown? Br
A. B. C. D.
2-bromobicyclo[4.2.2]decane 3-bromobicyclo[4.2.2]decane 7-bromobicyclo[4.2.2]decane 8-bromobicyclo[4.2.2]decane
12.
What is the major organic product of the following reaction?
CH3CO2H + CH3NH2
13.
A. CH3CONHCH3
B. CH3COONHCH3
C. CH3COO NH3CH3
D. CH3COO-NH4+
Which of the following compounds is the weakest base?
A.
B.
NH C.
NH2 D.
NH2
N 14.
Which of the following pathways is the best for the synthesis of m-bromotoluene (the formula is shown below) from benzene?
Br CH3
A.
CH3COCl AlCl3
B.
D.
FeBr3
CH3COCl Zn(Hg) AlCl3
C.
Br2
CH3Br AlCl3 CH3Br AlCl3
HCl
Zn(Hg) HCl Br2 FeBr3
HNO3
H2
NaNO2
H2SO4
Pt
HCl, -5 oC
H3PO2 H2O heat NaNO2
HNO3
H2
Br2
H2SO4
Pt
FeBr3 HCl, -5 oC
Br2 FeBr3 H3PO2 H2O heat
15.
Which of the following is the strongest acid?
OH
OH
A.
16.
OH
CH3
NO2 C.
B.
NH2
D.
Which of the following statements about the relative stabilities of the structures shown is TRUE?
H
CH3
H
H
H
CH3
H
CH3
II
I
H
H
H
CH3 A. B. C. D. 17.
OH
I has more torsional strain. I has more steric strain. II has more torsional strain. II has more steric strain.
Which of the following terms does NOT describe the carbohydrate shown? CHO HO H
H OH CH 2OH
A. L sugar 18.
B. Reducing sugar
C. Aldose
D. Tetrose
How many signals are present in the 13 C spectrum of the following compound? CH3 CH3
A. 3
B. 4
C. 5
D. 6
19.
What reagents would you use to carry out the following transformation? Br ------>
CH2 CH2 OH
A. Mg, then CH2 =O, then H3 O B. Mg, then CH3 CH2 I, then H2 O C. Mg, then CH3 CH=O, then H3 O O D. Mg, then , then H3 O
20.
Which of the following carbocations is the LEAST stable? A.
21.
B.
C.
D.
What is the name of the compound shown? OCH3
Br Cl A. B. C. D. 22.
3-bromo-4-chloroanisole 3-bromo-4-chloroaniline 1-chloro-2-bromo-4-anisole 1-bromo-2-chloro-5-aniline
Which of the following compounds will react the SLOWEST with Cl2 /FeCl3 ?
O A.
B.
Br C.
OCH3 D.
23.
What functional group does the following molecule contain?
OH OCH3
A. Lactone 24.
B. Hemilactone
C. Acetal
D. Hemiacetal
What is the structure of phthalic anhydride? O
O
O O
A.
O
B.
O
C.
O
D. O
O
25.
O
O
Which of the following compounds gives the SLOWEST SN1 reaction?
A.
CH2 CH3
CHCH 3 | Br
B.
Br C.
26.
CH2 CH2 Br
CH2 CH3
D.
Br
How would you carry out the following synthesis?
O OH
OCH2CH3
A. Add PCC then CH3 CH2 OH B. Add CrO3 /H2 O then SOCl2 then CH3 CH2 OH C. Add LiAlH4 then SOCl2 then CH3 CH2 OH D. Add PCC then SOCl2 then CH3 CH2 OH 27.
Which of the following is a secondary amine?
A.
NH2 B.
C. NH2
NHCH3
D.
N CH3
28.
What functional group is present in the molecule shown?
O S A. Sulfoxide 29.
B. Thioketone
C. Sulfone
D. Thioether
What is the product of the following sequence of reactions?
O
O
NaOC2H5 C6H5CH 2Br C2H 5OH
OCH2CH3 O
O
O
C 6H5
B.
A.
H3O + heat
OC 2 H5 CH2 C 6H 5 O
O
O D.
C.
C 6 H5
OH CH2 C 6 H5
30.
What is the dominant form of cysteine (shown below) at pH = 9? O pKa = 10.8 H N (conj. acid) 2
pKa = 1.7 OH CH2 SH pKa = 8.3
O .A H2 N
O CH2SH
.B H3 N
O
O
O O CH2SH
.C
H2 N
O CH2 S
D.
H3 N
O CH2S
31.
What compound has a molecular formula C10 H12 O and the following proton NMR spectrum: singlet, δ 2.1, 3 H multiplet, δ 3.0, 4 H multiplet, δ 7.1, 5 H C H2C H3 CH 2CHCHO
A.
C H2C H2C OC H3
B.
CH 3
D. C H3(C H2 )8CHO
C.
C OC H3
32.
Which of the following does NOT give a positive test with the compound shown? CH3CH2=CCH2 CH2 OH CH3 A. cold KMnO 4
33.
B. Br2 /CCl4
C. Ag(NH3 )2 +
D. Jones (chromic acid) reagent
Which of the following compounds is formed WITH ITS DIASTEREOMER as a product of the reaction shown?
CH3
Cl
H H
H
light + Cl 2 --------> ?
CH3 CH2 Cl A.
Cl H
H H
CH3 B.
Cl H
CH3 34.
CH3 Cl H
C.
Cl H
CH3
CH3 H Cl
CH3
D.
Cl H
H H CH2 Cl
Which of the following has an absorption maximum above 200 nm in its UV/Vis spectrum?
A.
B.
C.
D.
35.
Which of these reacts most rapidly with CH3 I/AlCl3 ?
A.
B. NO2
36.
C.
D.
NHCH3
OCH3
What is the product of the reaction shown?
O
+
H+ HOCH2CH2CH2OH
O
O
A.
B.
D.
O
What is the product of the reaction shown? 2 CH3CHOHCOOH O . A
heat
O
O
O
O
O
C.
B.
O O
38.
OH
C.
O
37.
CONH2
D.
O O
O
O
Which of the following is the strongest acid? COOH
COOH B.
A. CCl3 NO2
COOH C.
D.
Br NO 2
COOH
Br
CCl3 NH2
NH2
39.
What is the product of the reaction sequence shown? COCl 1. NH3 2. LiAlH4
NH2
CONH2
A.
CH2NH2 B.
CH3
COOH
C.
D. NH2
40.
What is the name of the following compound?
OH OH
A. B. C. D. 41.
Which of the following is the most stable carbocation? A. B. C. D.
42.
catechol resorcinol cresol diphenol
(C6 H5 )3 C+ (CH3 )2 CH+ CH3 CH=CHC +(CH3 )2 CH 2 =CH +
Which of the following is an intermediate involved in the reaction shown? C6 H5 CH=CH 2 + HBr peroxides A. C6 H5 CHCH 2 Br
B. C 6 H5 CHBrCH 2
C. C 6 H5 CHCH 3
D. C6 H5 CH2 CH2
43.
An unknown compound having the formula C7 H12 gave the compound shown when treated with O3 followed by Zn and H2 O. What is the structure of this unknown? O O || || CH3 CCH2 CH2 CHC-H | CH3
CH3
CH3 A.
CH3
CH3
B.
CH3 44.
D.
C.
CH3
CH3
CH3
What is the major product of the following reaction:
HNO3 H2 SO4 COCH3 A.
NO2
B.
SO3 H
C.
SO3 H
D.
NO2
NO2
COCH3
45.
COCH3
COCH3
COCH3
Compound X has the molecular formula C10 H12 O. The IR spectrum of X has a strong band near 1710 cm-1 . Compound X forms a phenyhydrazone, but gives a negative Tollens’ test and a positive iodoform test. What is the structure of the compound? O A.
CH2 -CH 2 -C-CH 3
CH B.
CH-CH-CH 3 OH O
O C..
CH2 -C-CH 2 -CH 3
CH 2 CH2 C-H
D. CH3
46.
What is the major organic product of the reaction shown? O NH 3
O
?
warm O O
O OH
A.
OH
NH 2
B.
OH
O 47.
O
O
C.
O
Mg ether
Br
H2 CrO4
(1) O (2) H 3 O
?
O A.
O B.
C OH
CH2 CH2 C
OH
O O C.
CH2 -O-CH 2 C
D. OH
NH 2 O
O
What is the final organic product of the following reaction sequence? CH 2
NH 2
N-H D.
CH2 - C OH
48.
What is the major product of the following reaction? O CH3 CH2 C
OH H
?
H2 O
O
O A.
CH3 CH2 CHCH 2 CH 2 C
H
B. CH3 CH2 CH
CHC
OH
CH3
OH
O
O C.
H
CH3 CH 2 CH CCH2 CH 3
D.
CH3 CH2 C OH
OH 49.
How could you convert an unsaturated fatty acid into a saturated fatty acid? A. KMnO4 , OHC. H2 , Ni, pressure
50.
B. OH -, H2 O, heat; then H3 0+ D. O 3 ; then Zn, H2 0
What product(s) would you expect from the following reaction? OCH 3 NaNH 2
Cl
NH 3
OCH 3 NH 2
OCH 3
?
OCH 3
NH 2 I A. I alone
NH 2 III
II B. II alone
C. III alone
D. I and II
