Organic Chemistry

1. Predict the product of the following carbon-carbon pi bond would be 13. Can form intramolecular hydrogen
reaction sequence. Ethyne + 1) lost bonds
excess NaNH2 2) excess I-CH2- d. The shorter bond length of the
(CH2)2-CH3-- double bond makes it more 14. Which of the following reactions is
a. 6-iodo-1-hexyne difficult for the attached groups to associated with the inversion of
b. 1-hexyne pass one another configuration of a chiral substrate?
c. 5-decyne e. The statement is incorrect- a. Nucleophilic Substitution
d. 1-iodo-1-hexene rotation around double bonds Bimolecular
does occur b. Elimination Unimolecular
2. The metal-catalyzed addition of c. Nucleophilic Acyl Substitution
hydrogen to an alkene occurs in 7. What is the major product from the d. Free radical Addition
what fashion? acid-catalyzed hydration of 2-
a. Syn methyl-2-pentene? 15. Which of the following is an
b. Anti a. 2-methylpentane essential fatty acid
c. Mixture of syn and anti b. 2-methyl-1-pentanol a. palmitic acid
d. neither syn nor anti c. 2-methyl-2-pentanol b. stearic acid
d. 2-methyl-3-pentanol c. lauric acid
3. Pyridinium chlorochromate (PCC) e. 1- methoxypentane d. linolenic acid
ia a commercially available
reagent that provides Cr6+ (as 8. How many electrons are involved
CrO3) and does not contain water. in a carbon-carbon triple bond?
It is useful for oxidizing primary a. 1
alcohols to aldehydes, and b. 2
secondary alcohols to ketones. c. 3
Which of the following compounds d. 4 16. Which of the following can
does not give an aldehyde upon e. 6 possibly give rise to meso
reaction with PCC? compound?
a. benzyl alcohol 9. Which of the following is a correct
b. cyclopentylmethanol statement about the carbon- 17. Which of the following is the
c. 2,2-dimethyl-1-butanol carbon triple bond in an alkyne? strongest Brønsted base?
d. 3-methyl-3-pentanol a. composed of one sigma bond
and one pi bond 18. Which of the following reactions
4. Which of the following statements b. composed of two sigma bond would not be useful for converting
best describes the most stable and one pi bond 4,4- diethylcyclohexanone into
conformation of trans 1,3- c. composed of one sigma bond 1,1-diethylcyclohexane?
dimethylcyclohexane? and two pi bond a. Wolff-Kischner reduction
a. Both methyl groups are axial d. composed of two sigma bond (N2H4, strong base & heat)
b. Both methyl group are and two pi bond b. Clemmensen reduction (Zn/Hg,
equatorial e. composed of one sigma bond, acid & heat)
c. one methyl group is axial, the one pi bond and one delta bond c. Thioacetal reduction (i
other is equatorial HSCH2CH2SH & BF3; ii H2 +
d. The molecule is severely 10. Which of the following is not used Raney Ni)
strained and cannot exist as primary standard for sodium d. LiAlH4 in THF & heat
hydroxide solutions?
5. Upon hydrogenation, which of the a. KHP 19. A C5H8 hydrocarbon is reacted
following alkenes releases the b. Benzoic Acid with BH3 in THF, followed by
least heat per mole c. Sulfuric Acid oxidation with alkaline hydrogen
a. 3,4-dimethyl-1-hexene d. Potassium biodate peroxide. Treatment of the
b. (Z)-3,4-dimethyl-2-hexene resulting product with PCC in
c. (E)-3,4-dimethyl-2-hexene 11. Which of the following nonpolar CH2Cl2 produces a chiral ketone,
d. (Z)-3,4-dimethyl-3-hexene e. molecules should have the highest formula C5H8O. What
(E)-3,4-dimethyl-3-hexene boiling point? hydrocarbon best fits these facts?
a. SF1 a. 1-methylcyclobutene
6. Carbon-carbon double bonds do b. CH4 b. methylenecyclobutane
not undergo rotation as do carbon- c. CO2 c. vinylcyclopropane
carbon single bonds. The reason d. N2 d. cyclopentene
is that
a. the double bond is much 20. Determine the double bond
stronger and thus more difficult to stereochemistry (E or Z) for the
rotate following molecules.
b. overlap of the sp2 orbitals of the
carbon-carbon sigma bond would 12. The least reactive towards
be lost electrophilic aromatic substitution
c. overlap of the p orbitals of the
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Organic Chemistry
d. all of these

26. Conjugated alkenes are

characterized by
a. Alternating  and  bonds. b.
a. A: E, B: E Adjacent  bonds.
b. A: Z, B: Z
c.  bonds separated by two or
c. A: E, B: Z
more  bonds.
d. A: Z, B:E
d. A cyclic system containing 6
bonds.
21. Which of the following is/are
chiral?
27. Aryl ketones are prepared by the
following reaction. This reaction is
called _____ .

a. 1,2 and 3
a. Friedel-Crafts Alkylation
b. 1 and 2
b. Friedel-Crafts Acylation
c. Only 1
c. Wolff-Kishner reaction
d. Only 2
d. Hofmann rearrangement
22. How many chiral centers are there 28. Which of the following does not
in 3-bromo-2-pentanol? have a net dipole moment?
a. 2 a. H2O
b. 3 b. NH3
c. 4 c. BF3
d. 1 d. BrF5

29. Aldehydes and ketones are

reduced by NaBH4 or LiAlH4 to
yield ___ and ___ alcohols.
a. 10 and 20
23. What is the stereochemistry of the b. 20 and 10
following compound? c. 10 and 30
a.R d. 20 and 30
b.S
c.E 30. -bromination of carboxylic acid
d.Z by a mixture of Br2 and PBr3 is
called ____________.
24. How many gauche are present in a. Hell-Volhard Zelinskii (HVZ)
cis-1,4-dimethylcyclohexane? reaction
a. 1 gauche b. Robinson annulation
b. 2 gauche c. Claisen- condensation reaction
c. 3 gauche d. Michael reaction
d. 4 gauche

25. Which of the following used as a

suffix of carbaldehyde in naming?

a.

b.

c.

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Organic Chemistry
Answer Key

1. B
2. D
3. D
4. C
5. E
6. C
7. C
8. E
9. C
10. C
11. A
12. A
13. D
14. A
15. D
16. B
17. C
18. D
19. A
20. D
21. B
22. A
23. E
24. B
25. A
26. A
27. B
28. C
29. A
30. A