Organic Chemistry Practice Exam

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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 32003600 and 1650 cm-1. Compound C shows absorptions at 32003600 and 3000 cm-1. Both a and b are true. Answers a, b, and c are all true.

Br b. OH d. OH

c. d.

O e.

e.

2.

Why is the infrared absorption for the stretching of the carbon-carbon triple bond of internal alkynes rarely observed? a. They do not form cations. b. They are too strong. c. Observable bonds cannot be too symmetric. d. They don’t have hydrogens attached to them.

5.

Which of the following statements is (are) true about the infrared spectrum of the compound shown below? O N C CH2 C CH2CH2Br

a. It shows absorptions at 3000-3150 cm-1 and 1720 cm-1. b. It shows absorptions at 3000-2850 cm-1 and 2250 cm-1. c. It shows absorptions at 2250 cm-1 and 1650 cm-1. d. It shows absorptions at 2250 cm-1 and 1720 cm-1. e. Both b and d are true.

3.

Which of the reagents/techniques listed below would serve as the basis for a simple chemical test to distinguish between CH3CH2CH=CHCH2CH2CHO and CH3CH2CH=CHCH2CH2CH2OH ? a. b. c. d. e. KMnO4 Br2 in CCl4 IR spectroscopy PCC Both c and d

CHM 2211-U02 PRACTICE EXAM I, Page 4 6. Which Grignard reaction could be used to synthesize : 8. OH CH3 CH2CH2 C CH3

Which of the labeled hydrogens absorbs furthest upfield in the NMR? H H H C C C CH3 H H C O H H H H H C A B D E

CH3

O a. CH3 CH2CH2 COCH3 O b. CH3 CH2CH2 CH O c. CH3 CH2CH2 CH + CH3 CH2MgBr O d. CH3CHCH2 MgBr CH3 + CH3 CH + CH3 MgBr + 2CH3 MgBr

a. A

b. B

c. C

d. D

e. E

9.

7.

How many peaks would be seen for each of the circled protons in the compounds below? CH3 CH3 C O H A H H CH3 H H C H CH3 H H H H C C C C H H H H B CH3 CH3

How many different kinds of protons are present in each of the following molecules? O A. (CH3)2CH C OCH(CH3)2 B. CH3CH2 O CH2CH3

C. CH3CH2NH2

D.

a. A: 1; B: 5; C: 2 b. A: 2; B: 5; C: 1 c. A: 1; B: 5; C: 1 d. A: 2; B: 5; C: 2 e. A: 1; B: 3; C: 1

E.

a. A: 4; B: 2; C: 1; D: 4; E: 3 b. A: 3; B: 2; C: 3; D: 1; E: 3 c. A: 4; B:...
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