MINISTRY OF INDUSTRY
CENTER FOR INDUSTRIAL EDUCATION AND TRAINING
BOGOR HIGH SCHOOL OF CHEMICAL ANALYST
Jl. Binamarga I, Ciheuleut, Phone (0251) 323138, Fax (0251)384785
PO BOX 2017, Bogor Timur 16143
FINAL EXAM SEMESTER 3
ACADEMIC YEAR 2009-2010
Subject
Class
Day, Date
Time
Teachers
:
:
:
:
:
Organic Chemistry
XI-5 & XI-6 (RSBI Class)
Monday, November 30, 2009
07.30-09.30
Rusman, M.Si
Instructions:
1. The exam contains 5 pages. There are 40 questions (35 multiply choices & 5 essays).
Make certain you have all parts to the exam.
2. Point values for each question are indicated in brackets [points], total points = 100
3. Please read each question carefully and answer each part. Make your answers clear and
legible. Unreadable answers will be considered incorrect.
4. Use a pencil to fill answer sheet and a pen to answer essay questions .
5. You have 120 minutes to complete the exam.
A. MULTIPLE CHOICES
Read carefully!. Choose one alternative that best completes the statement or answers the
question! ( 52.5 points @ 1.5 point)
1. Which of the following statement is not
describes the “vital force theory”?
A. All organic compounds come from
living organism
B. Organic compounds can not be
synthesis in laboratory scale
C. Organic compounds can not be obtain
from inorganic compounds
D. Urea is an inorganic compound is
produced in laboratory so that vital
force theory is died
E. Is needed vital force to produces
organic compound
A.
B.
C.
D.
E.
4. What is the condensed structural formula
for an alkane with five carbon atoms?
A. CH3CH2CH2CH2CH3
B. C5H12
C. C-C-C-C-C-C
D.
H
2. Look at to the table below !
NO
1
2
3
4
5
6
CaCl2 soluble in hexane
NaHCO3 soluble in water
Mineral oil soluble in water
Octane soluble in water
CCl4 soluble in water
PROPERTIES
Flammable
High solubility in water
Solution is conductor
Exhibits covalent bonding
Exhibits isomerism
High boiling point
H
H
H
H
H
H
C
C
C
C
C
C
H
H
H
H
H
H
H
E.
5. What is the molecular formula for the
following compound?
Base on the table, the properties of C6H14
showing by number:
A. 1,2,3
B. 2,4,6
C. 2,3,6
D. 1,3,5
E. 1,4,5
3. Water is a polar solvent and hexane is a
non polar solvent. Which of the following
correctly describes the solubility of the
solute?
A. C10H22
B. C12H22
C. C12H24
D. C12H26
E. C14H28
1
6. How many tertiary carbon atoms are there
in the molecule shown below?
14. In the presence of ultraviolet radiation,
alkanes react with bromine. How many
mono bromination product of isobutane
are possible?
A. None
A. 0
B. 1
C. 3
D. 4
E. 8
7. Which of the following compounds is an
organic compound?
A. n-heptane
B. 1-methylcyclopentene
C. 3-methylcyclohexene
D. 1,3-hexadiene
E. 2-methylbutane
9. The common name for 2,2-dimethylpropyl
is:
A. Isobutyl
D. neopentyl
B. t-butyl
E. Isopentyl
C. s-butyl
10. What is the name of the unbranched
alkane with twelve carbon atoms?
A. Decane
B. Undecane
C. Dodecane
D. Tridecane
E. Tetradecane
A. 3
12.
D. CnHn
E. CnH2n+1
All of the choices listed are
representations of the same molecule
Except :
B.
CH3
E.4
B. 4
C. 5
D. 6
E. 8
A. Be insoluble in either solvent layer
B. Partition mostly in the lower solvent
layer
C. Partition mostly in the upper solvent
layer
D. Partition equally between the two layer
E. Be soluble only in aqueous CaCO3
17. Alkanes are prepared by reaction below,
Except:
A.
B.
C.
D.
E.
Catalytc idrogenation of alkane
Hydrolysis of Grignard reagent
Wurtz reaction
Dehydrogenation of alcohols
Corey-House synthesis
18. Which
alkene would
yield
3methylpentane when subjected to catalytic
hydrogenation?
H
A.
A. (CH3)2CHCH2CH3
CH3
D. 3
16. Caffeine is soluble in both aqueous
solution and dichloromethane. The
solubility of caffeine in water is 2.2 g/100
mL and the solubility of caffeine in
dichloromethane is 10.2 g/100 mL. If
caffeine is shaken with a mixture of
aqueous CaCO3 and dichloromethane,
the caffeine will…(CH2Cl2, density = 1.35)
11. Which of the following is the general
formula for a cycloalkane?
A. CnH2n+2
B. CnH2n
C. C2nH2n
C. 2
15. Propane is commonly used as a fuel of
heating. Write the balanced chemical
equation for the complete combustion of
propane. How many moles of oxygen
react with one mole of propane when
complete combustion occurs?
A. CH2F2 B. CO C.CS2 D. HCN E. N2H4
8. Which of the following is unsaturatedaliphatic hydrocarbon
B. 1
B.
H2C CH2 CH2
D.
C C
H
CH 2CH 2CH3
H
H
C C
H
C. (CH3)2CH(CH3)2
D. CH3CH2CH2CH2CH3
E.
H3 C
H
CHCH2CH 3
H3 C
E.
CH2 CH3
C C
H
H 2 C CH2 CH2 CH 2 CH 3
CH 3
CH 3
H 3C
C.
H
C C
H
CH 2CH 2CH3
13. As a general rules, the boiling point of
alkane increase roughly 30oC every
carbon added to the chain. If boiling point
of n-butane is 10.2oC, so, the boiling point
of ethane is (oC):
A. -18.8 B. -49.8 C. 40.2 D.49.8 E.70.2
2
19. According to Markovnikov,s rule, when
HCl reacts with the molecules shown,
which product will result?
(CH3)2C=CHCH3 + HCl
23. What is the condensed structural formula
for the product of the hydrogenation of 2butene using a platinum catalyst?
?
CH3
A. (CH3)2CHCHClCH3
B. (CH3)2CClCH2CH3
C. (CH3)2CClCHClCH3
D. (CH3)2CHCH2CHCl2
E. Non of the above
20. Ozonolysis (O3 + Zn/H2O) of alkenes will
result in:
CH3
CH 2
CH
B.
H 3 C CH 2 CH 2 CH3
C.
H3 C CH
CH3 CH 2 CH
CH 3
CH
CH3
OH
E.
H 3C
HC
CH 3
24. Which of the following is the IUPAC name
for the compound below?
CH 3
and
HC
D. H3C CH 2 CH CH3
21. Which of the following pairs of formulas
represent structural isomers?
CH 3
H 3C
Cl
A. The formation of aldehydes and/or
ketones
B. The formation of carboxylic acids
C. The formation of alcohols and ethers
D. The formation of esters
E. Aldehyde only
A.
A.
CH 3
CH3
CH3
Br
CH3
B.
H 3C
CH
CH 3
CH
and
CH 3
CH 3 CH2 C
CH 3
A.
CH3 CH 2 CH 3
B.
CH 3
C.
H3 C CH 2
and
CH 2 CH3
Cl
CH 3
C.
CH3
D.
H3 C
C
and
CH3
D.
CH3 CH 2 CH 3
CH3
E.
E.
CH3
CH2
and
CH3 CH2 CH 2
CH 2
CH 3
25. What is the name of the compound
shown below?
CH 3
22.
Which of
cycloalkene?
the
1-Chloro-2-bromo-4-methyl-3,5cyclohexadiene
1-Bromo-6-chloro-3-methyl-2,4cyclohexadiene
2-Methyl-5-chloro-6-bromo-1,3cyclohexadiene
6-Bromo-5-chloro-2-methyl-1,3cyclohexadiene
3-Bromo-4-chloro-1-methyl-1,5cyclohexadiene
compounds
is
H
a
CH 2CH 3
C C
H 3C
A.
B. H 2C
CH
CH
CH2
A.
B.
C.
D.
E.
H
trans-3-pentene
cis-3-pentene
trans-2-pentene
cis-2-pentene
2-pentene
C.
D.
H 3C
C
CH2
H 3C
E.
3
26. Which of the following molecules can
exist as geometric isomers?
CH3
H
(B) CH2 C
(A)
CH3
(D) CH3CH2CHCH3
(C)
CHCH2CH3
Cl
(E) CH3CH CHCH3
32. The kind of reaction that involved the
reaction of alkylhalide with sodium metal
in anhydrous ether is called:
A.
B.
C.
D.
E.
Wurtz reaction
Hydrolysis of Grignard reagent
Dehydrohalogenation of alkylhalide
Hydrogenation of alkene
Corey-House synthesis
Cl
27. The reaction of 2-butene with Br2 in CCl4
solution yields:
A.
B.
C.
D.
E.
1-bromo-2-butene
2-bromo-butene
1,2-dibromobutane
2,2-dibromobutane
2,3-dibromobutane
28. The reaction of 1-butene with water in the
presence of sulfuric acid will result in
formation of:
A. Butane
B. 1-butanol
C. 2-butanol
D. 1-butene
E. Cyclobutane
29. Which of the following is the IUPAC name
for the compound below?
33. The addition of HBr to propene in the
presence of peroxide produces:
A. 1-bromopropane
B. 2-bromopropane
C. 1,1-dibromopropane
D. 2,2-dibromopropane
E. 1,2-dibromopropane
34. The common name for 2-methyl-2pentyne
A.
B.
C.
D.
E.
Methyl isopropylacetylene
Ethyl isopropylacetylene
Isopropyl ethylacetylene
Ethyl propylacetylene
Ethyl 1-methylethylacetylene
35. What is the IUPAC name for this
compound?
CH 3
Br
A. 1-methyl-3-bromo-2-cyclohexene
B. 2-bromo-6-methylcyclohexene
C. 3-bromo-1-methyl-2-cyclohexene
D. 1-bromo-3-methylcyclohexene
E. 1-bromo-3-methyl-2-cyclohexene
HC
A.
B.
C.
D.
E.
C
CH
CH 2
CH
CH
CH 3
3-methyl-1-heptyn-5-ene
3-methyl-5-hepten-1-yne
5-methyl-2-hepten-6-yne
5-methyl-8-heptyn-2-ene
5-methylheptenyne
30. Which molecule can have cis-trans
isomer?
A. CH3CH=C(CH3)2
B. (CH3)2C=CHCH3
C. CH3CH=CHCl
D. CH3CH=CCl2
E. Br2C=CH2CH3
31. Which of the following are pairs of
position isomer?
A. 3-methylheptane & 3-ethylheptane
B. n-pentane & 2-methylbutane
C. 2-pentene & 2-methyl-2-butane
D. 1-pentene-2-methyl1-butene
E. 2-methyl-1-butene & 2-methyl-2-butene
4
B. ESSAY (47.5 points)
Write the best answer for the following questions!
1. Give the IUPAC name for the following compounds! (15 points)
A.
D.
H
B.
C
H3C
H
C
C
C
C
C
C
C
C
H
CH
C
CH 2
H
E.
CH3
C.
Br
CH
Br
C
H
H
H
CH 3
CH3
C
C
CH2
CH3
H
H
C
Cl
C
H
CH
CH2
CH
Cl
H
C
CH 2
C
H3 C
C
CH 3
Cl
CH3
CH3
H
2. Write equation for the preparation of following compound! (7.5 points)
A. n-butane from 1-bromobutane
B. 2,3-dimethylbutane from n-propylbromide
C. 2-methylpropane from 2-methylpropene
3. How does 2-methylpropene react with: (14 points)
A. Cl2
B. HBr
C. HOCl
D. Conc. H2SO4
E. Diluted cold KMnO4
E. Conc. hot KMnO4
F. O3, Zn/H2O
4. A hydrocarbon A, added one mol hydrogen in the presence of platinum catalyst to form nhexane. When A is oxidized with hot concentrated KMnO4, a single carboxylic acid containing
three carbon atoms is isolated. Give the structure and name of A! (6 points)
5. A hydrocarbon X reacts with concentrated sulfuric acid to form an alkylhydrogen sulphate which
O
on hydrolysis yields 2-butanol. On ozonolysis X gives formaldehyde ( H
C
H ) and
O
propionaldehyde ( CH 3 CH 2 C
H ). What is the structural formula of X? (5 points)
Good Luck and Good Thinking!
5