Organic Chemistry Flashcards

1
Q

Friedrich Wohlers work on isomerism
was able to curb the growth of vitalism
by disproving the old notion that organic
compounds can only come from organic
sources. Which among the following was
the product produced in Wohler’s
synthesis?
A: Ammonium Cyanate B: Urea
C: Carbon Disulfide D: Acetic Acid

A

b

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2
Q

Who among the following constituted
the concept of resonance in order to take
explain the structures of molecules or
ions that are not accounted for by the
octet rule?
A: August Kekule B: Linus Pauling
C: Gilbert Lewis D: Robert Robinson

A

b

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3
Q

Which among the following statements
highlights the actual difference between
Lewis Structures and Resonance
A: Lewis structures shows how the atoms
of a molecule are bonded to one another
while the resonance represents the
different substituent combinations
B: Lewis structures focuses on the
localization of electrons while resonance
features the electrons capacity of being
delocalized among the atoms
C: Resonance structures represent the
various ways in which a molecule can be
drawn while the Lewis structure
represents the accepted “True” structure
of the molecule
D: A resonance structure and Lewis
structure are virtually indistinguishable
from one another

A

b

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4
Q

Determine whether each of the
following statements pertaining to
constitutional isomers is TRUE or FALSE.
[a.] They have the same molecular formula
[b.] They have the same molecular weight
[c.] They have the same connectivity to
their atoms
[d.] They have the same physical
properties

A

b

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5
Q

Explain the difference in structure
between a saturated hydrocarbon from an
unsaturated hydrocarbon.
A: Any of these
B:A saturated hydrocarbon only contains
carbon-carbon single bonds while an
unsaturated hydrocarbon contains one or
more carbon-carbon double or triple bonds
C: A saturated hydrocarbon is used mainly
in cheaper forms of gasolines for vehicle
use while unsaturated hydrocarbons
compose most of the gasoline formulae
used by current gasoline manufacturers
D: A saturated hydrocarbon can no longer
accept any hydrocarbon or inorganic
element, and compound while an
unsaturated hydrocarbon is more flexible
in reaction mechanisms

A

b

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6
Q

Which among the following can be the
possible structures of a molecule that
has the molecular formula C5H8?
A: Alkane and Alkene with a single double
bond
B: Alkene with a single double bond and
Alkyne with a single triple bond
C: Cycloalkane and an Alkene with two
double bonds
D: Cycloalkene with a single double bond
and two rings

A

d

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7
Q

An entomologist extracted pheromone
samples from a moth captured in the wilds
of Maguindanao. Based on a spectroscopic
analysis, the molecule is a 2-methyl
branched alkane. If it has a molecular
weight of 254, what is the IUPAC name of
the alkane?
A: 2,3-dimethylhexadecane
B: 2-methylheptadecane
C: 2,2,4-trimethylpentadecane
D: 2-methyloctadecane

A

b

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8
Q

Which among the following represents
the impact of Odd Hassel’s work in the
field of Organic Chemistry?
A: The difference between Eclipsed
Conformation and Staggered Conformation
observed in alkanes
B: The chair conformation of cyclohexane
C: The measurement of the dihedral angle
observed in gauche conformation
D: The identification of the various
sources of strain a cyclohexane may
experience

A

b

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9
Q

Which among the following statements
best describe the most stable
conformation of 1-isopropyl-3-
methylcyclohexane?
A: The methyl substituent is attached in
the equatorial position at C3 and is
trans to the isopropyl substituent at C1
B: The isopropyl substituent is attached
in the equatorial position at C1 and is
trans to the methyl substituent at C3
C: The methyl substituent is attached in
the axial position in C3 and is cis to
the isopropyl substituent at C1
D: The isopropyl substituent is attached
in the axial position at C1 and is cis to
the methyl substituent at C3

A

b

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10
Q

Which has a higher absolute entropy
at a temperature of 25 deg C,
cyclopropane or propylene? Why?
A: Both have the same absolute entropy at
normal temperature
B: Propylene due to the free rotation
around the carbon-carbon single bond
C: Cyclopropane due to the free rotation
around the carbon-carbon double bond
D: None of these

A

b

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11
Q

Which among the following statements
is true regarding the boiling point and
density of an unsubstituted alkane and a
halogen-substituted alkane?
A:Both the boiling point and density of a
halogen-substituted alkane is larger than
that of its unsubstituted alkane
counterpart.
B: Both the boiling point and density of
an unsubstituted alkane is larger than
that of its halogen-substituted alkane
counterpart.
C: The boiling point of an unsubstituted
alkane is larger than its halogen
substituted counterpart but their density
are equal.
D: The density of a halogen substituted
alkane is larger than that of its
unsubstituted alkane counterpart but
their boiling points are the same.

A

a

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12
Q

How is a carbocation stabilized by
the alkyl groups attached to it?
A: The alkyl groups release an electron
density on the positively charged carbon
in order to disperse the positive charge
B: The electrons that are sigma to the
positively charged carbon has its orbital
overlap with the vacant p orbital of the
positively charged carbon
C: The leaving group transfers some of
its electrons to the carbocation in order
to disperse the positive charge
D: The electrons in the alpha-Carbon
hydrogen bonds greatly distributes the
positive charge as opposed to the betacarbon hydrogen bonds

A

a

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13
Q

Which among the following reagents
will not synthesize cyclohexanol if the
starting material is cyclohexene?
A: [1] Diborane, [2] Hydrogen Peroxide,
Sodium Hydroxide
B: Bromine and Water
C: Water with Sulfuric Acid
D: [1] 9-BBN, [2] Basic Hydrogen Peroxide

A

b

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14
Q

Which among the following organic
compounds will be produced when 2,4-
dimethyl-3-pentanol is heated to 120 deg
C in the presence of sulfuric acid?
A: 2,4-dimethyl-1 pentene
B: 2,4-dimethyl-2-pentene
C: Both A and B
D: Neither A and B

A

c

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15
Q

Which among the following sequence of
organic reactions will produce 1-bromo-2-
propanol if the starting material for the
synthesis is 2-propanol
A: [1] H2SO4, heat [2] B2H6, diglyme [3]
basic H2O2
B: [1] H2SO4, heat [2] Br2, H2O
C: [1] H2SO4, heat [2] Peroxyacetic acid
D: Synthesis is not feasible with the
given starting material

A

b

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16
Q

A chemical engineering student is
studying the reaction mechanism of a
certain compound V. In one of the runs,
compound V was dissolved in methanol and
subsequently reacted with ozone, forming
compound W. Compound W later underwent
reduction through a reaction with
dimethyl sulfide forming Acetone and
Acetaldehyde. Identify Compound V.
A: 3-methyl-2-butene B: 2-methyl-1-butene
C: 3-methyl-1-butene D: 2-methyl-2-butene

A

d

17
Q

Who among the following proposed the
idea correlating Molecular Geometry and
Valence Electron Pairs that would later
become the Valence Shell Electron Pair
Repulsion (VSEPR) Theory?
A: Nevil Sidgwick B: Ronald Nyholm
C: Herbert Powell D: Ryutaro Tsuchida

A

b

18
Q

What is the Nujol Mull in organic
chemical reactions?
A: It is a mass spectrum technique and is
obtained by grinding up a solid which is
mixed with mineral oil to form a
suspension for IR spectroscopy
B: It is the name of a type of paraffin
oil from India and most often used in gas
chromatography to enhance the mass
transfer properties of compounds
C: It is a process applied for inorganic
compounds to determine the effervescence
of the compound under study
D: It is suspension in mineral oil which
is placed in between HgCl, AgI, and KCl,
or stainless-steel plates to obtain a
good spectrum.

A

a or d

19
Q

What are sigmatropic rearrangements
in organic reactions?
A: They are similar to the (3,3) cope
rearrangement where the beta ring of a
steroid undergoes photon activated retroelectrocyclization
B: They are thermal reactions which do
not allow the formation of six membered
benzene ring with a cis or trans alkene
such as in the formation of Vitamin D3
C: They are different from electrolytic
reactions wherein movement of a sigma
bond with a simultaneous rearrangement of
the pi-system does not occur
D: They are not the same to the (3,3)
cope arrangement and the beta ring does
not undergo photon activated retro
electrocyclization

A

a or c

20
Q

Determine whether each of the
following statements is TRUE or FALSE
[a] A molecule containing a stereogenic
center automatically indicates that it is
a chiral molecule
[b] A molecule with two chirality
centers, having an R,S configuration
respectively has an enantiomer whose
chirality centers have an R,R
configuration
[c] A molecule with an S configuration
for its single chirality center is bound
to display a Levorotatory response when
placed in a polarimeter
A: T, T, T B: T, F, T
C: F, T, F D: F, F, F

A

d

21
Q

A sample of cholesterol, weighing
70.5 mg was submitted to the laboratory
to analyze its optical activity. The
sample was dissolved in 300 mL of
chloroform before placing it in a 25 cm
sample tube and inserting it into the
polarimeter, installed with a newly
bought sodium lamp. If the observed
rotation of the plane-polarized light is
zero degrees, which among the following
is the identity of the sample?
A:100% (+)-cholesterol
B:100% (-)-cholesterol
C:50% (+)-cholesterol,50% (-)-cholesterol
D:None of the above

A

c

22
Q

. In the study of fats and lipids, determine which
of the two triglycerides has a higher melting point,
substance A containing only lauric acid and
glycerol, or substance B containing only stearic
acid and glycerol?
A. B
B. A
C. Both have the same melting point
D. None of these

A

a

23
Q

. In the study of fats and lipids, determine which
of the two triglycerides has a higher melting point,
substance A containing only lauric acid and
glycerol, or substance B containing only stearic
acid and glycerol?
A. B
B. A
C. Both have the same melting point
D. None of these

A

a

24
Q

. Adrenaline is produced in the body through a
biochemical nucleophilic substitution reaction
where:
A. The leaving groups are larger and more complex
than the halogen atoms frequently in nucleophilic
substitution reactions.
B. According to Markovnikov’s rule, the
biosynthesis of epinephrine adds hydrogen atoms
to the double banded carbon atom.
C. The nucleophilic nitrogen atom of
norepinendrine from a covalent bond with the CH3
of S adenosylmethionine
D. The reactant neocleophile atom replaces the
leaving group in the nucleophylic substitution
reaction.

A

d

25
Q

. These compounds are formed by the reaction of
acids with alcohols.
C. Bases
A. Ethers
B. Esters
D. Enzymes

A

b

26
Q

n a dehydration reaction where water is lost,
an organic compound C3H80
reacts with concentrated phosphoric and a product
is formed. This
product rapidly decolorizes a solution of bromine
in tetrachlormethane.
What is a product?
A. Propanol
B. Propanolol-2
C. Propene
D. Propanol-1

A

c

27
Q

In the deacetylation of acetyl histone, what is
the reactant equation?
A. Histone - (CH2) 4-NH3+ +-CH3-COOO
Acetylation→ Histone – (CH2) 4-NH-C-CH3
B. all of these
C. Histone - (CH2)4-NH3++CH3 - COO
acetylation<Histone -(CH2)4-NH-CH ->
Deacetylation
D. 2 Histone- (CH2)4-NH3++4 CH3-COO -> 4
Histone- (CH2) 4-2NHO

A

c