Sample Final Examination
Organic Chemistry I
CHEM 2423
H OH
OH O
HO
H
HO
H
H
H
OH
Practice Exam A
Name ___________________________________________
CHEMISTRY 2423 Practice FINAL EXAM A
DIRECTIONS: A periodic table is attached at the end of this exam. Please answer all questions as
completely and clearly as possible, showing all your work.
Part I. Nomenclature and Structures (2 points each)
1.
Give the correct IUPAC name for the following structures (2 pts each):
H
Br
(a)
Br
Br
CH(CH3 )2
C=C
CH3
(b)
H
(c)
(a) _______________________________________________________________
(b) _______________________________________________________________
(c) _______________________________________________________________
2. Draw the structure that corresponds to the following name (2 pts each):
(a) (S)-2-bromobutane
(b) (E)-3-iodo-2-pentene
(c) 2,2-dimethyl-3-hexyne
Part II. Multiple choice. Circle the one best answer. (2 points each)
3. What is the correct hybridization for the indicated carbon atoms.
CH3
CH
CH
(A) sp2, sp
CH3
(B) sp3, sp
(C) sp3, sp2
(D) sp, sp2
4. What functional groups are present in the following molecule?
O
CH3 - CH - CH2 - C- OH
OH
(A) alcohol and carboxylic acid
(B) ketone and ether
(C) alcohol and ester
(D) ketone and aldehyde
5. Which one of the following structures is the most stable conformation for 2-bromo butane
(viewing down the C2-C3 bond axis)
Br
Br
H
CH3
Br
CH3
CH3
CH3
(A)
(B)
H
CH3
CH3
CH3
H
(C)
Br
H
CH3
CH3
(D)
6. Identify the number of primary, secondary, and tertiary carbons, respectively, in the
following molecule:
(A) 1, 3, 1
(B) 4, 1, 1
(C) 2, 4, 2
(D) 2, 2, 4
(C) CH3-
(D) CH3OH2+
7. What is the conjugate acid for CH3OH?
(A) CH3O-
(B) CH2OH-
8. Describe the indicated C-H bond indicated below in terms of orbital overlap:
CH3-CH=CH2
(A) sp3-sp3
(B) sp3-sp2
(C) sp2-1s
(D) sp-1s
9. Which one of the following groups has the highest priority?
O
C
CH3
CH2
(A)
OH
OH
(B)
(C)
(D)
10. Rank the following according to the most acidic to least acidic.
I) HCl
II) CF3-COOH
(A) I>II>III
III) CH3-COOH
(B) II>I>III
(C) III>II>I
(D) II>III>I
11. What is the relationship between the two compounds:
and
(A) enantiomers
(B) diastereomers
(C) same molecule
(D) none of these
12. Which reaction intermediate is formed by the following reaction?
Br2 / CCl4
Br
Br
Br
Br
Br
(A)
(B)
(C)
(D)
13. Which one of the following alkenes is the most stable?
(A)
(B)
H3C
CH3
H3C
(C)
C
CH2
CH2
H3C
(D)
CH3
H3C
CH3
H3C
CH3
C
H3C
CH2 CH3
C
C
H
14. Which one of the following carbocation intermediates is the least stable?
15. Which one of the following substances is referred to as a Gilman reagent?
(A) CH3I
(B) (CH3)2CuLi
(C) CH3MgBr
(D) CH3Li
16. An allylic hydrogen is indicated at which position in the structure below?
CH3 - HC = CH C C - H
(A) 1
(B) 2
(C) 3
(D) 4
17. Which one of the following diagrams correctly illustrates the displacement of bromine
by hydroxide via SN2 reaction?
(A)
HO-
(B)
Br
CH3
HO-
(C)
H3C
Br
HO-
(D)
H3C
Br
HO-
Br
CH3
18. Inversion of configuration results from which one of the following mechanisms?
(A) E1
(B) E2
(C) SN1
(D) SN2
19. Which one of the following molecules has the highest boiling point?
(A) CH3CH2CH3
(B) CH3CH2COCH3
(C) CH3CH2CH2OCH3
(D) CH3CH2CH2OH
20. What sequence correctly descrides the steps involved in a radical chain reaction?
I) initiation
(A) I, III, II
II) termination
(B) I,II,III
III) propagation
(C) III, I, II (D) none of these
5
21. Which of the following are examples of syn addition to an alkene?
(A) hydrogenation and hydration
(B) hydrobromination and hydroboration
(C) hydration and hydrobromination (D) hydrogenation and hydroboration
22. Which one of the following hydrogens is the most acidic?
CH3 - HC = CH C C - H
(A) 1
(B) 2
(C) 3
(D) 4
23. The following process demonstrates:
O
OH
(A) resonance (B) conjugation
(C) racemization
(D) tautomerism
24. What reagent is needed to convert 1-hexyne to 2-hexanone?
(A) O3 /Zn/ H3O+
(B) PCC (pyridinium chlorochromate)
(C) BH3 /H2O2 /OH-
(D) HgSO4 / H2SO4 / H2O
25. In mass spectroscopy,
(A) the sample is irradiated with infrared radiation
(B) the heat of combustion of the sample is measured
(C) the sample is bombarded with a stream of high energy electrons
(D) the sample is irradiated with ultraviolet radiation
26. Select the structure of a compound with the molecular formula C6H14 which has a
base peak at m/e = 57 in the mass spectrum.
(A) CH3CH2CH2CH2CH2CH3
(B) (CH3)2CHCH2CH2CH3
(C) (CH3)3CCH2CH3
(D) (CH3)2CHCH(CH3)2
Part III. Reactions (2 points each)
Give the major product(s) of each of the following reactions. Show all relevant stereochemistry. (2
pts each)
CH3
Br2 /hv
CHCH2CH3
27.
CH3
28.
29. CH3 C
CH + HCl (1 eq)
Br
30.
31.
CCl4
+ Br2
ether
KOH
NBS
+
1) O3
32.
2) Zn/H3O
CH2 I2 / Zn(Cu)
33.
1) BH3, THF
34.
2) H2O2, H
35.
CH3 - CH2 - C
C Na
1) CH3Br
2) H2 / Lindlar catalyst
36.
CH = CH - C
C-H
excess H2
Pd / C
7
Part IV. Synthesis (3 points each)
Show by a series of reactions how you could prepare the following compounds from the indicated
starting compound. Be sure to clearly indicate the reagent used in each step.
37.
O
38.
H
CH3
H
C=C
C=C
CH3
CH3
CH3
39.
CH2 CH3
Part V. Mechanisms (3 points each)
Write a complete mechanism for the following reactions. Show all intermediate structures, formal
charges, and electron flow using the curved arrow convention.
(3 pts each)
40.
CH3
CH3
1) KOH
Br
2) HBr
Br
41.
CH3
CH3
OH
H2SO4
Heat
Part VI. Spectra (5 points)
Use the mass spectrum for a hydrocarbon shown below to answer questions 42 - 44.
42. What is the base peak (1 pt)?
43. What is the parent ion peak (1 pt)?
44. What is the structure of the compound (3 pts)?
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CHEMISTRY 2423 Practice FINAL EXAM A (Answers)
PART I. (2 points each)
1. (a) 4-bromo-3-ethylheptane
(b) 1,3-dibromo-1,3-cyclohexadiene
(c) trans-4-methyl-2-pentene
2.
H
CH3
Br
C=C
H
CH2 CH3
CH3
CH2 CH3
CH3
CH3 - C - C
C - CH2 - CH3
I
(c)
CH3
(a)
(b)
PART II. (2 points each)
3. A
4. A
5. B
6. C
7. D
8. C
9. A
10. A
11. C
12. D
13. B
14. B
15. B
16. A
17. B
18. D
19. D
20. A
21. D
22. D
23. D
24. D
25. C
26. C
PART III. (2 points each)
27.
29.
28.
CH3
Cl
H
C=C
CH3 - C - CH2 - CH3
or others ( R &S)
Br
Br
CH3
Br
30.
31.
CH3
CH3
CH3
Br
CH2
+
major
minor
+
Br
CH3
11
CH3
O
33.
32. H - C - CH2 - CH2 - CH2 - C - H
34.
35.
CH3
CH3 CH2
C=C
OH
H
CH2 CH2 CH2 CH3
36.
PART IV. (3 points each)
37.
O
H gS O
B r2
C C l4
B r
C H - C H
- B r
2S O
38.
CH3
H
C = C
C = C
H
CH3
H 2 / L i d la r c a ta ly s t
B r2
CH3 - CH - CH - CH3
CH3
CH3
2 KOH
C - CH3
CH3 - C
Br
Br
39.
C H
C H
H I
I
(C H
C H
)2 C u L i
12
, H
2 K O H
- H
PART V. (3 points each)
40.
CH3
CH3
OH
.. + H2O + :Br :
..
Br
H
AND
CH3
CH3
H - Br
....
CH3
-
: Br :
..
Br
H
H
41.
CH3
CH3
O-H
O- H
H+ - OHSO3
CH3
H2SO4
CH3
E1
:OHSO3
PART IV. (5 points) (1+1+3)
42.
44.
m/e- = 43
43. m/e- = 72
CH3 - CH - CH2 - CH3
CH3
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