O-Chem Final exam
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Texas A&M University, Kingsville *
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Course
3325
Subject
Chemistry
Date
Feb 20, 2024
Type
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46
Uploaded by valexander600
EXAM 2
Question:
A bicyclic alkane contains 12 carbon atoms. How many hydrogen atoms does
it contain?
ANSWER
:
22
Question:
When a mole of octane undergoes complete combustion, how many moles
of water are formed?
ANSWER:
9
Question:
What is the major constituent of natural gas?
ANSWER:
methane
Question:
Which of the molecules below can be properly called an amine?
ANSWER:
CH
3
CH
2
NHCH
3
Question:
Provide an acceptable name for the following compound.
ANSWER:
4,4-dichloro-6-isopropyl-3-methylnonane
Question:
A branched alkane has ________ boiling point relative to the isomeric linear alkane. There
are ________ London force interactions in the branched alkane.
ANSWER:
a lower; weaker
Question:
When one compares the densities of n-hexane and water, one finds ________.
ANSWER:
that
n
-hexane is less dense than water
Question:
Using the general molecular formula for alkanes: Predict the molecular formula of the C22
straight-chain alkane.
ANSWER:
C22H46
Question:
Triacontane is an unbranched alkane that contains 30 carbon atoms in each molecule. How
many hydrogen atoms are present in each molecule of triacontane?
ANSWER:
62
Question:
Use the following structure for the question below. Saquinavir Structure
Which of the
following functional groups is not present in the HIV protease inhibitor drug called Saquinavir?
ANSWER:
Ketone
Question:
Which molecule below is an ether?
ANSWER:
CH 3CH 2OCH 2CH 3
Question:
Which intermolecular force is primarily responsible for the interactions among alkane
molecules?
ANSWER:
van der Waals or London forces
Question:
Provide the name of the compound shown.
ANSWER:
2,2,7-trichloro-4-ethyl-6-isobutyl-7,10-dimethyldodecane
Question:
Provide an acceptable name for (CH
3
CH
2
CH
2
)
3
CH.
ANSWER:
4-propylheptane
Question:
Which of the statements below accurately describe(s) alkanes? Answer: V.
I, II and III
Question:
Provide the name of the compound below.
Answer:
3-fluoro-2,2-dimethylhexane
Question:
How many carbons do the primary alkane constituents of gasoline contain?
Answer:
C
5
—C
8
Question:
Provide an acceptable name for the alkane shown below.
ANSWER:
3-ethyl-7-methyl-5-propylnonane
Question:
A series of compounds, like the
n
-alkanes, that differ only by the number of -CH2-
groups, is called a(n) ________ series.
Answer:
Homologous
Question:
Name the haloalkane shown. CH
3
CH
2
C(CH
3
)
2
CH
2
CH
2
I
Answer:
1-iodo-3,3-dimethylpentane
Question:
Which molecule below is an alkene?
Answer:
(CH
3
)
2
C=CH
2
Question:
In the complete combustion of heptane, how many moles of water are
produced?
Answer:
8
Q
uestion:
Use the following structure for the question below. Saquinavir Structure
Which functional group occurs more than two times in the structure of the HIV protease
inhibitor drug called Saquinavir?
Answer:
Amide
Question:
Consider the three isomeric alkanes n-hexane, 2,3-dimethylbutane, and 2-methylpentane.
Which of the following correctly lists these compounds in order of increasing boiling point?
Answer:
2,3-dimethylbutane < 2-methylpentane <
n
-hexane
Question:
identify the correct IUPAC name for the following structures.
Answer:
4-(2-iodo-1-methylethyl)-3-methylheptane
Question:
Vildagliptin is a recently released antidiabetic drug (
J. Med. Chem.
2010
, 7902). Name
each functional group in vildagliptin.
Answer: HO= Tertiary Alcohol
HN= Secondary Amine, O and N= Amide, NC= Cyanide
EXAM 3
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Question:
Determine whether the following compounds are constitutional isomers
Answer:
The compounds are not constitutional isomers. They
are just two different representations of the same compound. They are both 2,3-dimethylbutane.
Question:
The twisted boat conformation of cyclohexane is actually a slightly lower energy conformation
than the boat conformation. Which of the following accurately describes one factor involved in this
structural behavior?
Answer:
fewer unfavorable steric factors in the twisted boat
Question:
Using Bond Dissociation enthalpies from Table 4-2, Calculate heat of reaction for
propagation steps in bromination of methane (Calculate unit kcal/mol) Br
2
+ CH
3
-CH
3
------------->
CH
3
CH
2
- Br +HBr
Answer: -14
Question:
An increase in which of the following results in a decrease in the rate of a reaction?
Answer:
energy of activation
Question:
Among the butane conformers, which occur at energy minima on a graph of potential energy
versus dihedral angle?
Answer:
gauche and anti
Question:
Which of the following has a conformer with two equatorial alkyl substituents?
Answer:
cis
-1,3-diethylcyclohexane
Question:
From the options below, select the choice which shows the two chair conformations
of the following compound.
Answer:
Question:
How many transition states are in the following reaction coordinate diagram?
Answer: 2
Question:
Give the IUPAC name for the cycloalkane shown below.
Answer:
cis
-1-isopropyl-3-methylcycloheptane
Question:
Based on the following reaction coordinate diagram, which compound, A or C, is formed
faster from B? Which is more stable, A or C?
Answer:
A is
formed faster; C is more stable than A. A is in higher energy and C has lower free energy than A so C is
more stable.
Question:
In the reaction of Cl
2
with ethane and UV light, which of the following reactions would be a
termination event(s)?
I)
∙CH3 + ∙CH
3
→ CH
3
-CH
3
II)
Cl∙ + CH
3
-CH
3
→ CH
3
-H
2
C∙ +
HCl
III)
Cl∙ + CH
3
-H
2
C∙ →
CH
3
-CH
2
-Cl
IV
)
Cl
2
+ CH
3
-H
2
C∙ → CH
3
-CH
2
-Cl + Cl∙
V)
C l∙ + Cl∙ → Cl
2
Answer: reactions I, III and V
Question:
Which of the following correctly lists the conformations of cis-1,4-di-t-butylcylcohexane in
order of increasing energy?
Answer:
twist boat < boat < chair < half-chair
Question:
If a monocyclic alkane hydrocarbon contains n carbon atoms, how many hydrogen atoms
must it also contain?
Answer: 2n
Question:
Which intermolecular force is primarily responsible for the interactions among alkane
molecules?
Answer:
van der Waals or London forces
Question:
Place the following alkanes in order of increasing boiling point: CH
3
(CH
2
)
6
CH
3
,
CH
3
(CH
2
)
5
CH
3
, (CH
3
)
3
CCH
2
CH
2
CH
3
Answer:
(CH
3
)
3
CCH
2
CH
2
CH
3
< CH
3
(CH
2
)
5
CH
3
< CH
3
(CH
2
)
6
CH
3
Question:
How many monochlorinated product can be predicted in Chlorination of Pentane ?
Answer:
3
Question:
Provide the name of the compound shown.
Answer:
2,2,7-trichloro-4-ethyl-6-isobutyl-7,10-dimethyldodecane
Question:
Select the energy diagram of a reaction with the following characteristics. A one-step reaction
with a negative Δ
G:
Answer:
Question:
How many secondary hydrogens does the following compound have?
Answer: 8
Question:
Choose the correct chair conformation. For your chair, make sure that it contains three sets of
parallel lines
Answer: Boat, Chair, Twist boat, half
chair
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Question:
In reaction coordinate diagram shown below which step has the greatest activation energy in
the
reverse direction
?
Answer:
E going to C
Question: Identify the compound 2,5,6-trimethyloctane below: Answer:
Question:
Select an energy diagram showing the conformational analysis of 2,2,3,3-tetramethylbutane.
Answer:
Question:
Rank the three carbocations shown below in terms of increasing stability. I
II
III.
Answer:
III, II, I
Question:
Explain why the lowest energy conformation of decane is an extended, or
zig-zag conformation.
Answer:
The lowest-energy conformation for any straight-chain
alkane is the one with all the internal carbon-carbon bonds in their anti conformations.
These anti conformations give the chain a zigzag shape.
Question:
Which is the rate-determining step in the conversion of A to G in the reaction coordinate
diagram shown below?
Answer:
It would
be step C to E, because it involves a higher activation energy.
Question:
arrange the following Newman projections of butane in order of energy.
Answer:
I<III<II<IV
Question:
Which of the following contributes to make Δ
G
° more negative?
Answer:
a more positive
Δ
S
°
Question:
The structures below are ________.
Answer:
structural isomers
Question:
Bromination of propane is slower rate than chlorination but bromination is more selective
then chlorination. Which of the following is true about higher selectivity and slower rate of bromination
than clorination?
Answer:
In bromination C-H bond is nearly broken in transition state and greater radical character where as in
chlorination C-H bond is just begining to break so less radical charater., First propagation step(rate
limiting step) energy maxima of bromination resembles to product than reactant. The bond dissociation
energy of first propagation step (H-Cl formation) in chlorination (exotherminc process) is higher than (H-Br
formation) in Bromination (Endothermic process). Endothermic process are more selective than
exothermic processes
Question:
Which of the following is the least stable conformer of 1-
tert
-butyl-3-methylcyclohexane.
Answer:
tert
-butyl is axial and the methyl is axial.
Exam 4
Question:
What two atomic orbitals or hybrid atomic orbitals overlap to form the C—C π bond in
ethylene?
Answer:
C p + C p
Question:
Provide the proper IUPAC name for the alkene shown below.
Answer:
6-bromo-1-methylcyclohexene
Question: Name the alkene shown. Be sure to include the appropriate
E
or
Z
label
necessary.
Answer:
(
E
)-1-bromo-4-chlorohept-3-ene
Question: What is the major product of the following reaction?
Answer:
Question: Which of the following is the least stable carbocation? Answer:
Question: Which of the following mechanisms (S
N
1, S
N
2, E1, E2) feature(s) a
carbocation intermediate?Answer: both S
N
1 and E1
Question: When (
cis
)-1-bromo-2 methylcyclohexane is treated with methanol and heat,
four different products are formed — two by substitution and two by elimination.
Which of the
following conditions would change the outcome of this reaction by promoting the
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production of 3-methylhexene as the major product?
Answer:
tert
-butoxide/
tert
-butyl alcohol
Question:
Which of the compound do not have dipole moment ?
Answer:
trans-2,3-dichlorobut-2-ene
Question:
How many elements of unsaturation do molecules with a molecular formula
of C
6
H
6
Cl
6
have?
Answer:
1
Question: Which of the following species is the least nucleophilic? Answer:
H2O
Question: Predict the two most likely mechanisms that occur when iodocyclohexane is
heated in methanol Answer:
E1 and S
N
1
Question:
What is the value of Δ
H
° in kcal/mol for the reaction shown below?
(CH3)3C—H + Br—Br→ (CH3)3C—Br + H—Br
Bond energies are:
(CH3)3C—H = 74 kcal/mol
(CH3)3C—Br = 73 kcal/mol
Br—Br = 45 kcal/mol
H—Br = 88 kcal/mol
Answer: -42
Question: Which of the following is the most likely structure of the following cation after
rearrangement (hydride shift) ?
Answer: D
Question:
Which of the following carbocations is likely to rearrange?
Answer:
II and IV
Question:
Which alkyl halide undergoes an S
N
2 reaction most rapidly?
Answer:
Question:
When (
S
)-1-bromo-1-phenylethane undergoes an S
N
2 reaction with methanethiol (CH
3
SH), the product of the reaction is the compound shown below. What is its configuration?
Answer:
R
only
Question:
The Gibbs free energy shows that the free energy
△
G
° ________.
Answer:
increases as
both
K
eq and T increase
Question:
Which of the following compounds will undergo the fastest S
N
1 reaction?
Answer: IV
Question: Which of the following is the most stable carbocation?
Answer: IV
Question:
Provide the proper IUPAC name for the alkene shown below.
Answer:
(
E
)-3,5-dimethylhex-2-ene
Question:
What product results from the S
N
2 reaction between (
S
)-2-chloropentane and ethoxide ion?
Answer:
(
R
)-2-ethoxypentane
Question: Identify all chirality centers in each of the following compound:
Answer:
Question:
Which of the following S
N
2 reactions is the slowest?
Answer:
Question:
Which of the following alkenes has the largest molar heat of hydrogenation (ie,
releases the most heat upon hydrogenation)?
Answer: 1-hexene
Question:
Name the following compound:
Answer:
2-methyl-1,4-pentadiene
Question: T
he carbon-carbon bond length in ethylene is ________ than the carbon-carbon bond length
in ethane, and the HCH bond angle in ethylene is ________ the HCH bond angle in ethane
Answer:
shorter; larger than
Question:
Which of the following best describes the geometry about the carbon-carbon double
bond in the alkene below?
Answer:
E
Question: Identify whether each of following pairs of compounds are enantiomers or
diastereomers:
Answer: diastereomers
Question: What stereoisomer is the major product obtained from the following E2
reaction?
Answer:
Question:
S
N
2 reactions usually proceed with ________.
Answer:
complete inversion at the
asymmetric center undergoing substitution
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Question:
Dehydration of an unknown alcohol with concentrated H
2
SO
4
results in the formation of all
of the following alkene products. What is/are the possible structures of the original alcohol?
Answer:
QUIZ 2
Question: Anisole, the compound shown below, is an example of _______
Answer: an ether
Question:
D
opamine is shown below. What functional group, or structural
element is not present in this compound?
Answer: carboxyl group
Question:
Provide an acceptable name for the alkane shown below.
Answer:
2,2,3,6-tetramethylheptane
Question:
Provide an acceptable name for the alkane shown below.
Answer:
2,5-dimethylheptane
Question:
Provide the IUPAC name of (CH
3
)
2
CHCH
2
CH
2
C(CH
3
)
3
.
Answer: 2,2,5-trimethylhexane
Question: W
hich of the class of organic compound below contains a carbonyl
group as a part of its structure?
-
Ester
-
aldehyde
-
Carboxylic acid
-
Ketone
-
All of the above
Answer: all of the above
Question: Which of the molecules below can be properly called a nitrile?
CH
3
COOH
CH
3
CH
2
CH
2
NO
2
CH
3
CH
2
CH
2
OH
CH
3
CN
CH
3
CH
2
NHCH
3
Answer: CH
3
CN
Question:
Which of the molecules below is an ester?
CH
3
COOH
CH
3
OCH
2
CH
2
CH
3
CH
3
CH
2
CH(CH
3
)
2
HC≡CCH
3
CH
3
COOCH
3
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Answer:
CH
3
COOCH
3
Question: Place the following alkanes in order of increasing boiling point:
CH 3(CH 2) 6CH 3, CH 3(CH 2) 5CH 3, (CH 3) 3CCH 2CH 2CH 3
Answer: (CH3)3CCH2CH2CH3 < CH3(CH2)5CH3 < CH3(CH2)6CH3
Question:
Which of the following has the greatest solubility in CH3CH2CH2CH2CH2CH3?
CH3OH
CH3O
-
Na
+
CH3NH2
CH3OCH3
Answer: (CH3)3CH
Question:
How many constitutional isomers have a molecular formula of C
6
H
14
?
Answer: 5
Question:
Give the IUPAC name for
Answer:
4-Ethyl-3-methylheptane
Question: Identify an amine below
CH
3
CH
2
NHCH
3
CH
3
CH
2
CN
CH
3
CH
2
CONH
2
CH
3
CH
2
CHO
CH
3
COCH
2
CH
3
Answer: CH
3
CH
2
CONH
2
Question: Explain why gasoline does not dissolve in water.
Answer: Gasoline does not dissolve in water because they do not share similar
polarities. Water is polar because of the Oxygen creating dipole moments. Gasoline is
nonpolar and thus does not have any atoms creating dipoles. Therefore, the gasoline
can not be dissolved in the water because the bonds of each substance can not break
each others bonds, which explains the layers that are created when adding these two
together in a container.
Question: What is the common name of the following compound?
Answer: isobutane
Question: Which functional groups below indicate the presence of two atoms
connected by a triple bond?
A.
alkyne
B.
alkene
C.
nitrile
D.
ester
E.
both A and C
Answer: E
Question:
Which compound is more soluble in water? Briefly explain your choice.
CH
3
OCH
3
or
CH
3
CH
2
OH
Answer:
CH
3
CH
2
OH is more soluble in water since it can donate a hydrogen bond to water and
accept a hydrogen bond from water. CH
3
OCH
3
can only accept a hydrogen bond from water; it does
not have hydrogen which can hydrogen bond to water.
Question: Which of the functional groups below contain a hydroxyl group as a part of
their structure?
A.
aldehyde
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B.
alcohol
C.
carboxylic acid
D.
amine
E.
B and C only
Answer: e
Quiz 3:
Question:
Identify the relative positions of the methyl groups in the most stable conformer of
butane viewed along the C2–C3 bond?
Answer: anti
Question: Which line angle(dash-wedged) drawing best represents the Newman
Projection shown below?
Answer:
Question:
Arrange the following conformers of butane in order of energy, lowest to
highest: eclipsed, totally eclipsed, gauche, and anti.
Answer: anti < gauche < eclipsed < totally eclipsed
Question:
Which of the following is a staggered conformer for rotation about the
C1—C2 bond in the following compound?
Answer: I
Question: Among the butane conformers, which occur at energy minima on a graph of
potential energy versus dihedral angle?
Answer: gauche and anti
Question: If a monocyclic alkane hydrocarbon contains n carbon atoms, how many
hydrogen atoms must it also contain?
Answer: 2n
Question:
Which conformers of butane, viewed along the C1–C2 bond, has the
lowest energy?
Answer: anti conformer
Question:
Which of the following statements about the conformers that result from rotation
about the C2-C3 bond of butane is correct
A.
The highest energy conformer is one in which methyl groups are
eclipsed by hydrogens.
B. The gauche conformer is eclipsed.
C. Steric strain is absent in an eclipsed conformer.
D. An eclipsed conformer is more stable than a
staggered conformer.
E.
none of the above
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Answer: E
Question: Name the haloalkane shown.
CH 3CH 2C(CH 3) 2CH 2CH 2CH 2 F
Answer: 1-Fluoro-4,4-dimethylhexane
Quiz 4
Question:
Which of the following correctly lists the conformers of cyclohexane in order of
increasing energy?
Answer: chair < twist-boat < boat < half-chair
Question: Given the following heats of combustion per CH 2 group within the structure,
which cyclic alkane has essentially no angle strain? (Ref: long-chain Alkane = 659
kJ/mol
Answer: cyclohexane = 659 kJ/mol
Question:
Name this compound
Answer:
Cyclopropylcyclopentane
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Question: The twisted boat conformation of cyclohexane is actually a slightly lower
energy conformation than the boat conformation. Which of the following accurately
describes one factor involved in this structural behavior?
Answer: fewer unfavorable steric factors in the twisted boat
Question: Which of the following has a conformer with two equatorial alkyl substituents?
A. 1,1-dimethylcyclohexane
B.
cis
-1,2-dimethylcyclohexane
C.
trans
-1,3-diethylcyclohexane
D.
cis
-1,3-diethylcyclohexane
E.
cis
-1,4-diethylcyclohexane
Answer: D
Question: Which line-angle formula corresponds to the chair conformation shown
below?
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Answer: III
Question:
Identify the correct IUPAC name for the structure shown below.
Answer: 5-bromo-1-tert-butyl-2-chlorocycloheptane
Question:
Which of the following correctly ranks the cycloalkanes in order of increasing
ring strain?
Answer: cyclohexane < cyclopentane < cyclobutane < cyclopropane
Question: Which of the following is the most stable conformer of
bromocyclohexane?
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Answer: III
Quiz 6
Question:
Some molecules are chiral even though they lack a chirality center. For example,
consider the following two compounds shown, and explain the source of chirality in each case:
Answer: This compound is chiral because steric hindrance prevents the two ring systems
from rotating with respect to each other, locking it in a particular conformation that is chiral
Question:
Which of the following terms best describes the stereochemical relationship of the two
compounds shown below in Fischer notation?
Answer: diastereomers
Question: Which of the following compound is chiral compound?
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A)
B C AND D
Answer: C
Question:
Calculate the % ee from the information provided below. The specific rotation of
pure adrenaline is -53° . A mixture of (
R
) - and (
S
)- was found to have a specific rotation of
-45° . The % ee of the mixture is
Answer: 85%
Question:
Provide the name of a Fischer projection shown below and assign configuration for
each assymmetric carbon.
Answer: (2
R
,3
R
,4
S
)-2,3,4-tribromoheptane
Question: Select the enantiomer of the following compound.
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Answer: D
Question:
Which of the following structures are achiral and meso?
Answer: 4
Q
uestion; Would a 50:50 mixture of (2
R
,3
R
)-2,3-dibromobutane and (2
R
,3
S
)-2,3-dibromobutane be optically active? Explain.
Answer: Yes, the mixture would be optically active. This is not a racemic mixture
but a mixture of diastereomers. The specific rotations of diastereomers are not
the same in magnitude nor necessarily opposite in sign.
Question: The relationship between I and II is: ________.
Answer: diastereomers
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Question: are isomers which have the same bonding sequence but differ in the
orientation of their atoms in space.
Answer: Stereoisomer
Question; Can a molecule be chiral if it contains no asymmetric carbons? Explain
briefly.
Answer: Yes. The presence of asymmetric carbons is not required for a molecule to
be chiral. The only requirement is that the molecule be nonsuperimposable with its
mirror image. Structural features other than asymmetric carbons can lead to
chirality.
Question: Rank the following from highest to lowest priority according to the
Cahn-Ingold-Prelog system: -F, -H , -OH , -SH.
Answer: -SH, -F, -OH, -H
Question:
What is the structural relationship between the two molecule shown below?
Answer: constitutional isomers
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Question: Compounds that rotate on the plane of polarized light clockwise are
called
Answer: Dextrorotatory
Question: Find the molecule that is stereoisomer of the compound on the picture.
Answer:
Question:
Identify whether each of following pairs of compounds are enantiomers or
diastereomers
Answer: diastereomers
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Question: Identify the enantiomer of the compound
Answer:
Question:
How many asymmetric carbon atoms are present in the following
compound?
Answer: 1
Question:
the specific rotation of pure (-)-2-butanol is -13.5°. If a mixture has a
specific rotation of +7°, how much of each form (+ and-) is present and what is the
e.e. of the mixture?
Answer:
The sample is 76% of the (+) and 24% of the (-). Therefore the e.e. is 52%
Question: How many diastereomers are there of the molecule shown below?
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Answer: 2
Question: Following compound possess carbon atoms chiral center that has
chirality center. Locate each of these chirality centers and identify the configuration
of each.
Answer:
Question: The stereochemical configuration of L-Threonine is (2
S
, 3
R
). Which of
the following structures corresponds to the correct configuration?
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Answer: I
Question: Which of the following configurations corresponds to the structure below?
Answer: (
4R
,
5R
)
Question:
Predict the specific rotation of the compound shown.
Answer:
Zero; the compound is achiral.
Question: A solution of 0.50g of (-) epinephrine dissolved in 20.0 mL water of dilute
aqueous HCl was placed in a 20 cm polarimeter tube. Using sodium D line , the
rotation was found to be -5.1° at 25°C. Determine specific rotation of epinephrine.
Answer: -102 degrees
Quiz 5
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Question: Which of the following describes the most stable conformer of
trans
-1-
tert
-butyl-3-methylcyclohexane?
Answer:
tert
-butyl group is equatorial and the methyl group is axial.
Question: which of the following correctly ranks the cycloalkanes in order of increasing
ring strain?
Answer:
cyclohexane < cyclopentane < cyclobutane < cyclopropane
Question: In the reaction of Cl 2 with ethane and UV light, which of the following reactions would
be a propagation event(s)
I)
Cl∙ + CH3-CH3 → CH3-CH2-Cl + H∙
II)
Cl∙ + CH3-CH3 → CH3-H2C∙ + HCl
III)
Cl∙ + CH3-H2C∙ → CH3-CH2-Cl
IV)
Cl2 + CH3-H2C∙ → CH3-CH2-Cl + Cl∙
V)
Cl2 + UV light → C l∙ + Cl∙
Answer: II and IV
Question:
Which of the following is the least the least stable conformer of 1-
tert
-butyl-3-methylcyclohexane.
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Answer:
tert
-butyl is axial and the methyl is axial.
Question:
Which conformer has the greatest energy in the potential energy diagram for
chair-chair interconversion of cyclohexane?
Answer: half chair
Question: Provide IUPAC name of following compound.
A
nswer: Cyclobutylcyclohexane
Question: Which of the following is a staggered conformer for rotation about the C1—C2
bond in the following compound?
Answer:I
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Question:
In the complete combustion of cycloheptane, how many moles of water are produced?
Answer: 7
Question:
What is the name of the following compound?
Answer:
1-chloro-2-methylcyclohexane
Question:
Describe the sources of angle strain and torsional strain present in cyclopropane.
Answer:
The angle strain arises from the compression of the ideal tetrahedral bond angle of
109.5° to 60°. The large torsional strain occurs since all C—H bonds on adjacent carbons are
eclipsed.
Question: Which of the following statements about the conformers that result
from rotation about the C2-C3 bond of butane is correct?
Answer: E
The gauche conformer is
eclipsed.
B.
An eclipsed conformer is more stable than a staggered conformer.
C.
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The highest energy conformer is one in which methyl groups are
eclipsed by hydrogens.
D.
Steric strain is absent in an eclipsed conformer.
E.
none of the above
Question: Explain why the lowest energy conformation of decane is an
extended, or zig-zag conformation.
Answer:
The lowest-energy conformation for any straight-chain alkane is the
one with all the internal carbon-carbon bonds in their anti conformations. These
anti conformations give the chain a zigzag shape.
Question: Does this Newman projection depict the conformer of the molecule
with the lowest-energy?
Answer: no
Question: Which conformers of butane, viewed along the C1–C2 bond, has the
lowest energy?
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Answer: anti conformer
Question:
How many carbons do the primary alkane constituents of gasoline contain?
Answer: C5 - C8
Question: Which of the following has a conformer with one equatorial
substituent and one axial substituent?
Answer
:
cis-1,4-dibromocyclohexane
Question: Which of the following has a conformer with two equatorial
alkyl substituents?
Answer:
Cis
-1,3-diethylcyclohexane
Question:
Give the IUPAC name for the cycloalkane shown below.
Answer:
trans
-1-ethyl-2-methylcyclopentane
Question:
Provide an acceptable name for the alkane shown below
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Answer: 2-fluoro-7-methyl-5-propyldecane
Quesrion: Name the alkane shown below.
Answer: 2,2,3,6-tetramethylheptane
Question:
Answer: 3,3,5-trimethylheptane
Question: most stable conformer of bromocyclohexane?
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Answer: III
Question: Which of the following best describes the molecules of a
sample of ethane gas at room temperature?
Answer: The molecules are rapidly interconverting between the eclipsed
and staggered conformations, but at any one time slightly more of them
are present in the staggered conformation
Question:
first propagation step of the free radical chlorination of methane, which of the
following occurs?
Answer: chlorine radical abstracts a hydrogen.
Question:
Are they the same?
Answer: no
Question:
following statements concerning the conformers of butane is true?
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.
There is more torsional strain in the anti conformer
than in the totally eclipsed conformer.
B.
Unlike ethane, all butane conformers are classified as
eclipsed.
C.
The lowest energy conformer of butane is the gauche
conformer.
D.
The gauche and anti conformers differ primarily in the
amount of nonbonded strain present.
E.
The eclipsed and totally eclipsed conformers have the
same amount of nonbonded strai
Answer: D
Question:
Which one of the following is the Lewis structure of tertiary-butyl radical?
Answer:
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Question:
Arrange in order of energy for butane
Answer:
.
I<III<II<IV
Quiz 7
Question:
Predict the product for the following reaction.
Answer: III
Question:
Predict the compounds in following pair that undergoes faster SN2 reaction.
Answer:
faster than
Primary R-X reacts faster than
2 degrees R-X.
faster than
Same neighboring
branching, so 1° is faster than 2°.
Question:
Which of the following is a strongest nucleophile in a polar protic solvent?
Answer:
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I
-
Question:
Provide name for the compound shown below:
Answer:
Methylene
Chloride
Question:
Under appropriate condition (S)-1-bromo-1-Fluoroethane reacts with sodium
methoxide to give pure(S)-1-fluoro-1-methoxyethane CH3CHBrF + NaOCH3--------->
CH3CHFOCH3 +NaBr Why is bromide rather than Fluoride replaced ?
Answer:
Bromide is much
larger in size wise and stablilizes negatvie charge through its valent of orbital. Meanwhile,
Fluoride is much smaller in size and has no valent of orbital.
Question:
Which of the following is the rate equation for the following reaction?
CH3CH2CH2CHBrCH3 + NaN3 CH3CH2CH2CHN3CH3 + NaBr
Answer:
Rate =
k[CH3CH2CH2CHBrCH3] [NaN3]
Question:
Although F is more electronegative than Cl, the C-Cl bond has a larger dipole moment
than the C-F Bond Explain.
Answer:
A Diploe moment is part of a product of a charge and the
distance between two dipoles. In C-F bond though a charge separation is more than its normally
partial charge developed is more between the distance of C and F is a small size of F atom. While
in C-Ci bond, through a partial charge developed is less, as a electronegativity of CI is less than F.
The distance between C and CI is much bigger due to the larger CI atom.. Therefore, the dipole
moment which is a product of distance and charge is greater for C-CI bond than C-F bond.
Question:
Which of the following is a geminal dihalide?
Answer:
3,3-dibromopentane
Question:
Consider the substitution reaction shown below. By what mechanism will the reaction
proceed?
Answer:
S N2
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Question:
Which of the following potential energy diagram represent an SN1 reaction?
Answer: II
Question:
What is the IUPAC name of the compound shown below?
Answer:
(1
R
,3
S
)-1,3-dichloro-1-ethyl-3-methylcyclopentane
Question:
Which of the following best describes the carbon-chlorine bond of an alkyl chloride?
Answer:
polar; δ+ at carbon and δ- at chlorine
Question:
Rank the following molecules in order of increasing relative rate of S N1 solvolysis with
methanol and heat (slowest to fastest reacting).
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Answer:
2 < 3
< 4 < 1 < 5
Question:
What set of reaction conditions would favor an SN2 reaction on
2-bromo-3-methylbutane?
Answer:
strong nucleophile in an aprotic solvent
Question:
Do all primary iodides react with N 3
-
at the same rate via the S N2 mechanism?
Explain.
Answer:
No, not all the primary alky react with N3- at the same rate that the SN2
mechanism does. Some primary are more likely hindered than others.
Question:
Which of the following are the polar protic solvents
Answer: I, IV
Question:
Choose the member of each pair that will react faster by SN1 mechanism. a) n-propyl
bromide or allyl bromide b) 2-bromo-2-methylbutane or 2-bromo-3-methylbutane
Answer: A)
Allyl bromide would react faster by SN1 mechanism.
B) 2-bromo-2-methylbutane reacts faster by SN1 mechanism.
Question:
The following reaction occurs via an SN1 mechanistic pathway:
Answer:
the rate of the reaction will be
doubled.
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Question:
In each case below, identify whether the substrate favors SN1, SN2, both, or neither:
Answer:
Neither,
Both,
SN2,
SN1
Question:
Polar aprotic solvent favor SN1 reactions?
Answer: False
Question:
Consider the substitution reaction shown below. By what mechanism will the reaction
proceed?
Answer: SN2
Question:
The light initiated bromination of cyclohexene using NBS (N-bromosucciniamide) gives
only one major product as shown below. Explain why there is no second product from an allylic
shift.
Answer:
Allylic
bromination of cyclohexene gives 3-bromocyclohex-1-ene regardless of whether there is an allylic
shift. Either pathway leads to the same product. If one of the ring carbons were somehow marked
or labeled, then the two products could be distinguished. (We will see in following chapters how
labeling is done experimentally.)This second structure from the allylic shift is
identical
to the first
structure—only one compound is produced here.
Question:
Which of the following is classified as a vinylic halide?
Answer:
CH 3CH═CHCl
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Question:
Provide the reagents necessary to carry out the following conversion.
Answer:
NaSH in DMSO
Question:
Which of the following is a secondary alkyl halide?
Answer:
isopropyl chloride
Question:
Name the haloalkane shown. Be sure to include the appropriate
R
or
S
description.
Answer:
(
R
)- 3-chloro-1,1-dimethylcyclohexane
Question:
Identify what reagents you would use to accomplish each of the following
transformations:
Answer:
C2H5O
-
Question:
Select the products of the following SN1 reaction.
Answer: A,C
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Click and drag to start drawing a
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Check
80
F3
DOD
BOD F4
X
MacBook Air
: □
0*
1/5
Julianna
?
000
Ar
2024 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibility
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1. hexyne
2. hexane
Organic Compounds
3. cyclohexene
4. 2-methylpentane
5. 2,3-dimethylbutane
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7. octane
8. nonane
9. heptane
♦
◆
+
The four molecules listed above that belong to a homologous series are numbered
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QUESTION 12
Which describes the functional group(s) of the following molecule?
CH;CHCCH3
CH3
O aldehyde
O ketone
O neither aldehyde nor ketone
O both aldehyde and ketone
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:0:
or
LiⓇ
Br
O..
O: K
H
:0:
H3C.. `CH3
H3C
`N'
CH₂
:0:
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of
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thing
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Eighth grade > * F.3 Calculate amounts of reactants or products in chemical reactions FVQ
Methanol can be used to prevent certain liquids from freezing in cold weather. Methanol is
produced when carbon monoxide and hydrogen gas react.
Questions
answered
Last chance
Consider the following reaction:
to stay in
stage 21
3 molecules of carbon monoxide (CO) react with 6 molecules of hydrogen (H,) to produce
Time
some amount of methanol (CH,O).
elapsed
Complete the table below.
25 23
00
HR MIN SEC
Chemical element Number of atoms in the reaction
Challenge
Stage 2 of 2
H
Get 4 correct
C
in a row
During this reaction, how many molecules of methanol (CH,O) are produced?
@
23
&
3
4
5
6
e
r
t
h
k
C
V
b
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