Organic Chemistry Practice Exam
Panther ID:
NAME:
FLORIDA INTERNATIONAL UNIVERSITY Department of Chemistry CHM 2211-U02– ORGANIC CHEMISTRY II
PRACTICE EXAM I
CHM 2211-U01 SAMPLE EXAM I, Page 2
Type of Vibration
C-H
Frequency (cm-1) 3000-2850 1450 and 1375 1465 3100-3000 1700-1000 3150-3050 1000-700 ca. 3300 2900-2800 2800-2700 1680-1600 1600-1400 2250-2100 1740-1720 1725-1705 1725-1700 1750-1730 1700-1640 1810 and 1760 1300-1000
Intensity s m m m s s s m w w m-w m-w m-w s s s s s s s
Alkanes -CH3 -CH2Alkenes
(stretch) (bend) (bend) (stretch)
CHARACTERISTIC INFRARED FREQUENCIES
(bend) Aromatic (stretch) (out-of-plane bend) Alkyne Aldehyde
C=C C C C=O
(stretch)
Alkene (stretch) Aromatic (stretch) Alkyne (stretch) Aldehyde (stretch) Ketone (acyclic) Carboxylic Acid Ester Amide Anhydride Alcohols, ethers, esters carboxylic acids Alcohols, phenols Free H-bonded Carboxylic acids Primary and secondary amines Nitriles Nitro
C-O O-H
NH C N N=O
3650-3600 3400-3200 3300-2500 ca. 3500 2260-2240 1600-1500 and 1400-1300
m m m m m s
-OH, -NH
CHEMICAL SHIFTS
CHCl3 H H
1H-NMR
12
O R C OH
11
R
10
O C H
9
R
8
7
6
H
5
CH2F
4
3
CH2Ar CH2NR2 CH2S
2
1
C H C C C-CH2-C C
0!
TMS
H
CH2Cl CH2Br CH2I
CHEMICAL SHIFTS
CH2O
C C-H C O CH2 C-CH3
carbonyl
aromatic; alkene
CH2NO2
alkane
13C-NMR
CH2
200
150 alkyne
100
50 C-O,N,X
0!
TMS
CHM 2211-U01 SAMPLE EXAM I, Page 3 MULTIPLE CHOICE QUESTIONS: Answer each of the following questions by bubbling in the correct response on the Scantron answer sheet. 1. What would be the final product in the following reaction sequence?
O
4.
Which of the following statements is (are) accurate about the IR spectra of compounds A, B, and C?
O OH OCH3
OH
1. PBr3 2. Mg/ether
1.
?
O+
A B C
2. H3
a.
O
OH c.
a. b.
Compound A shows absorptions at 3000 and 1700 cm-1. Compound B shows absorptions at
NAME:
FLORIDA INTERNATIONAL UNIVERSITY Department of Chemistry CHM 2211-U02– ORGANIC CHEMISTRY II
PRACTICE EXAM I
CHM 2211-U01 SAMPLE EXAM I, Page 2
Type of Vibration
C-H
Frequency (cm-1) 3000-2850 1450 and 1375 1465 3100-3000 1700-1000 3150-3050 1000-700 ca. 3300 2900-2800 2800-2700 1680-1600 1600-1400 2250-2100 1740-1720 1725-1705 1725-1700 1750-1730 1700-1640 1810 and 1760 1300-1000
Intensity s m m m s s s m w w m-w m-w m-w s s s s s s s
Alkanes -CH3 -CH2Alkenes
(stretch) (bend) (bend) (stretch)
CHARACTERISTIC INFRARED FREQUENCIES
(bend) Aromatic (stretch) (out-of-plane bend) Alkyne Aldehyde
C=C C C C=O
(stretch)
Alkene (stretch) Aromatic (stretch) Alkyne (stretch) Aldehyde (stretch) Ketone (acyclic) Carboxylic Acid Ester Amide Anhydride Alcohols, ethers, esters carboxylic acids Alcohols, phenols Free H-bonded Carboxylic acids Primary and secondary amines Nitriles Nitro
C-O O-H
NH C N N=O
3650-3600 3400-3200 3300-2500 ca. 3500 2260-2240 1600-1500 and 1400-1300
m m m m m s
-OH, -NH
CHEMICAL SHIFTS
CHCl3 H H
1H-NMR
12
O R C OH
11
R
10
O C H
9
R
8
7
6
H
5
CH2F
4
3
CH2Ar CH2NR2 CH2S
2
1
C H C C C-CH2-C C
0!
TMS
H
CH2Cl CH2Br CH2I
CHEMICAL SHIFTS
CH2O
C C-H C O CH2 C-CH3
carbonyl
aromatic; alkene
CH2NO2
alkane
13C-NMR
CH2
200
150 alkyne
100
50 C-O,N,X
0!
TMS
CHM 2211-U01 SAMPLE EXAM I, Page 3 MULTIPLE CHOICE QUESTIONS: Answer each of the following questions by bubbling in the correct response on the Scantron answer sheet. 1. What would be the final product in the following reaction sequence?
O
4.
Which of the following statements is (are) accurate about the IR spectra of compounds A, B, and C?
O OH OCH3
OH
1. PBr3 2. Mg/ether
1.
?
O+
A B C
2. H3
a.
O
OH c.
a. b.
Compound A shows absorptions at 3000 and 1700 cm-1. Compound B shows absorptions at