Deactivating Meta Directing Group Organic Chemistry Questions

Review Sheet for 6BL Final1. Running Reactions
a. Set up
i. Anhydrous conditions
ii. Reflux
b. Monitoring
i. How to prepare a TLC plate/TLC chamber
ii. What you can learn from TLC (how complete a reaction is, how pure something
is, comparing two compounds, etc.)
iii. How to find Rf
iv. Principles involved (mobile phase, solid phase, solvent polarity, etc.)
c. Work up
i. Extraction
ii. Washing
iii. Drying
iv. Filtration
v. Condensing
d. Purification
e. Percent Yield
i. Limiting reagent
f. Common Solvents
i. Name and Structures
2. Methods: Know how and why (See Appendix A and C)
a. Recrystallization
b. TLC
c. Column Chromatography
d. Extraction
e. Melting Point
f. Trituration
g. Phase Transfer Catalysis
3. Spectroscopy: Be able to use, interpret, and predict structures-See Spectral Reference Sheet
below. This will be provided for you on the exam. See Appendix B
a. IR
i. Functional group recognition
b. NMR
i. 1H-NMR
1. Splitting, integration, coupling
13
ii. C-NMR
1. Know where the different types of carbonyl carbons appear.
2. Peak height
c. Mass Spectrometry
i. M+ peak
ii. Base peak
iii. Isotopes of Halogens-Br, Cl in Mass Spec
iv. Common fragmentation patterns
1. Heterolytic vs. homolytic bond cleavage
2. Fragmentation of alkyl halides
3. Fragmentation of ethers and amines
4. Fragmentation of alcohols
5. Fragmentation of carbonyl compounds
6. McLafferty rearrangement
v. Predict fragmentation products
vi. Molecular formula from m/z peak
4. Reactions/Mechanisms: You are responsible for knowing the mechanisms of the starred (*)
reactions. For all the reactions (even those not starred) you should understand the general
principles of the reaction. Think about what you did during the experiment and why. What was
the electrophile and nucleophile? Think about the workup and why it was necessary to perform
the work up the way that you did. For example, if you washed a reaction mixture with an acidic
solution, why did you do that? What was it removing or changing? What would be the result if
you skipped the acid wash? Your lab reports (if done well) should be a big help in reviewing the
experiments. Also, for each reaction if I give you a similar reaction with slightly different
reagents you should be able to predict the product or go in the reverse direction, where if I give
you the product you can predict what the starting material was. You should also review the
discussion questions that are at the end of each experiment. Many students fail to do well on the
final because, rather than understanding the chemistry they simply memorize online answers to
discussion questions.
a. Fischer Esterification*
i. Acid catalysis
ii. Equilibrium
b. Phase Transfer Catalysis/Alkene Oxidation
c. Acid Chloride formation (including formation of Vilsmeier reagent)*
d. Polymerization*
e. Aldol Condensation*
f. Azo coupling (methyl orange)/Electrophilic aromatic substitution*
i. Chemistry of diazonium compounds
ii. Conjugation and Acid/base chemistry
g. Reductive Amination*
h. Grignard Reaction*
i. Dihydropyridine Synthesis*
j. Chemiluminescence
k. Gold Catalyzed Rearrangement (note: you don’t need to know the arrow pushing for the
last step of the mechanism)*
i. Understanding how to find and use coupling constants
l. Friedel-Crafts alkylation/acylation*
i. Activating/deactivating groups
ii. Directing groups
m. Electrophilic addition of alkenes*
n. Elimination of alkyl halides to form alkynes*
Chem 6BL Final Review Sheet
Gainer 2021
5. Other
a. Acid/Base chemistry-review general principles of acid/base equilibrium as it relates to
pKa.
b. For all experiments performed this quarter you should understand what you did during
the experiment/work-up/purification. For example, in the work up for the oxidation of
cyclohexene, you washed the crude solid with a basic solution. Why did you do this?
Why was it important to use a basic solution? What product or impurity was this reacting
with? Your lab reports, which should have focused on the why of each experiment (rather
than just rewording the experimental procedure) should be a good resource for this.
Chem 6BL Final Review Sheet
Gainer 2021
Review Sheet for 6BL Final
1. Running Reactions
a. Set up
i. Anhydrous conditions
ii. Reflux
b. Monitoring
i. How to prepare a TLC plate/TLC chamber
ii. What you can learn from TLC (how complete a reaction is, how pure something
is, comparing two compounds, etc.)
iii. How to find Rf
iv. Principles involved (mobile phase, solid phase, solvent polarity, etc.)
c. Work up
i. Extraction
ii. Washing
iii. Drying
iv. Filtration
v. Condensing
d. Purification
e. Percent Yield
i. Limiting reagent
f. Common Solvents
i. Name and Structures
2. Methods: Know how and why (See Appendix A and C)
a. Recrystallization
b. TLC
c. Column Chromatography
d. Extraction
e. Melting Point
f. Trituration
g. Phase Transfer Catalysis
3. Spectroscopy: Be able to use, interpret, and predict structures-See Spectral Reference Sheet
below. This will be provided for you on the exam. See Appendix B
a. IR
i. Functional group recognition
b. NMR
i. 1H-NMR
1. Splitting, integration, coupling
13
ii. C-NMR
1. Know where the different types of carbonyl carbons appear.
2. Peak height
c. Mass Spectrometry
i. M+ peak
ii. Base peak
iii. Isotopes of Halogens-Br, Cl in Mass Spec
iv. Common fragmentation patterns
1. Heterolytic vs. homolytic bond cleavage
2. Fragmentation of alkyl halides
3. Fragmentation of ethers and amines
4. Fragmentation of alcohols
5. Fragmentation of carbonyl compounds
6. McLafferty rearrangement
v. Predict fragmentation products
vi. Molecular formula from m/z peak
4. Reactions/Mechanisms: You are responsible for knowing the mechanisms of the starred (*)
reactions. For all the reactions (even those not starred) you should understand the general
principles of the reaction. Think about what you did during the experiment and why. What was
the electrophile and nucleophile? Think about the workup and why it was necessary to perform
the work up the way that you did. For example, if you washed a reaction mixture with an acidic
solution, why did you do that? What was it removing or changing? What would be the result if
you skipped the acid wash? Your lab reports (if done well) should be a big help in reviewing the
experiments. Also, for each reaction if I give you a similar reaction with slightly different
reagents you should be able to predict the product or go in the reverse direction, where if I give
you the product you can predict what the starting material was. You should also review the
discussion questions that are at the end of each experiment. Many students fail to do well on the
final because, rather than understanding the chemistry they simply memorize online answers to
discussion questions.
a. Fischer Esterification*
i. Acid catalysis
ii. Equilibrium
b. Phase Transfer Catalysis/Alkene Oxidation
c. Acid Chloride formation (including formation of Vilsmeier reagent)*
d. Polymerization*
e. Aldol Condensation*
f. Azo coupling (methyl orange)/Electrophilic aromatic substitution*
i. Chemistry of diazonium compounds
ii. Conjugation and Acid/base chemistry
g. Reductive Amination*
h. Grignard Reaction*
i. Dihydropyridine Synthesis*
j. Chemiluminescence
k. Gold Catalyzed Rearrangement (note: you don’t need to know the arrow pushing for the
last step of the mechanism)*
i. Understanding how to find and use coupling constants
l. Friedel-Crafts alkylation/acylation*
i. Activating/deactivating groups
ii. Directing groups
m. Electrophilic addition of alkenes*
n. Elimination of alkyl halides to form alkynes*
Chem 6BL Final Review Sheet
Gainer 2021
5. Other
a. Acid/Base chemistry-review general principles of acid/base equilibrium as it relates to
pKa.
b. For all experiments performed this quarter you should understand what you did during
the experiment/work-up/purification. For example, in the work up for the oxidation of
cyclohexene, you washed the crude solid with a basic solution. Why did you do this?
Why was it important to use a basic solution? What product or impurity was this reacting
with? Your lab reports, which should have focused on the why of each experiment (rather
than just rewording the experimental procedure) should be a good resource for this.
Chem 6BL Final Review Sheet
Gainer 2021
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Ch 2: Oxidation and Red x M IR Spectrum Table
x |
Interpreting IR Specta: A X
Carbon-13 NMR Spectro X
S SOLUTION: Organic Che X
GS Final Exam (page 1 of 13 X
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QUIZ Tlavigation
Question 1
Time left 0:59:45
Not yet
answered
A chemist sets up a reaction and lets it stir for 1 hour. After 1 hour, TLC chromatography is used to determine if the reaction is complete. The
starting material (SM) has a Rf value of 0.2 and the product (PD) has a Rf value of 0.6. Drag and drop the markers to show where the spots
would be if the reaction has not yet gone to completion but is forming product. (Left lane: starting material, middle lane: co-spot, right lane:
reaction mixture).
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3
4
5
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Ch 2 : Oxidation and Red * |
M IR Spectrum Table
x|
Interpreting IR Specta: A X
Carbon-13 NMR Spectro X
S SOLUTION: Organic Che X
GS Final Exam (page 2 of 13 X
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Question 2
A chemist is performing a Fischer Esterification but can’t find the sulfuric acid. This reagent is important because it
Not yet
answered
1
2
3
4
5
6
7
8
Points out of
4.00
However, the chemist does find the following reagents: 3M HCl(aq), brine, Aliquat 336, and Na2SO4. Which reagent should the chemist use in
place of the sulfuric acid, or will none of them be suitable substitutes?
10
11
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13
Flag
question
removes water from the reaction
acts as the catalyst
travels between the aqueous and organic phase
Finish attempt …
the chemist should use 3M HCl(aq)
the chemist should use brine
the chemist should use Na2S04
Time left 0:59:27
none of them are suitable substitutes
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Ch 2: Oxidation and Red x M IR Spectrum Table
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Interpreting IR Specta: A X
Carbon-13 NMR Spectro X
S SOLUTION: Organic Che X
GS Final Exam (page 1 of 13 X
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QUIZ Tlavigation
Question 1
Time left 0:59:45
Not yet
answered
A chemist sets up a reaction and lets it stir for 1 hour. After 1 hour, TLC chromatography is used to determine if the reaction is complete. The
starting material (SM) has a Rf value of 0.2 and the product (PD) has a Rf value of 0.6. Drag and drop the markers to show where the spots
would be if the reaction has not yet gone to completion but is forming product. (Left lane: starting material, middle lane: co-spot, right lane:
reaction mixture).
2
3
4
5
Points out of
2.00
10
11
12
13
Flag
question
Finish attempt …
–
–
—–
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SM
PD
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Sat Aug 28 7:04 AM
Ch 2 : Oxidation and Red * |
M IR Spectrum Table
x|
Interpreting IR Specta: A X
Carbon-13 NMR Spectro X
S SOLUTION: Organic Che X
GS Final Exam (page 2 of 13 X
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Question 2
A chemist is performing a Fischer Esterification but can’t find the sulfuric acid. This reagent is important because it
Not yet
answered
1
2
3
4
5
6
7
8
Points out of
4.00
However, the chemist does find the following reagents: 3M HCl(aq), brine, Aliquat 336, and Na2SO4. Which reagent should the chemist use in
place of the sulfuric acid, or will none of them be suitable substitutes?
10
11
12
13
Flag
question
removes water from the reaction
acts as the catalyst
travels between the aqueous and organic phase
Finish attempt …
the chemist should use 3M HCl(aq)
the chemist should use brine
the chemist should use Na2S04
Time left 0:59:27
none of them are suitable substitutes
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Ch 2: Oxidation and Red * |
M IR Spectrum Table
x |
Interpreting IR Specta: A X
Carbon-13 NMR Spectro X
S SOLUTION: Organic Che X
GS Final Exam (page 3 of 13 X
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Question 3
How does gold help to catalyze the reaction in the gold catalysis experiment?
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7
8
a.
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It coordinates to the methanol, making methanol a better nucleophile.
b. It deprotonates the methanol, making methanol a better nucleophile.
It donates electron density to the alkyne, making the alkyne a better nucleophile.
d. It coordinates to the alkyne, making the alkyne a better electrophile.
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TOCANITA DADDADA
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Carbon-13 NMR Spectro X
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Time left 0:58:56
Question 4
Which compound produces the 1H-NMR spectrum seen below? The multiplicies of the signals are (from left to right): doublet of doublets,
doublet, octet, singlet, doublet. The signal at 6.1ppm has a coupling constant of 14.8 Hz.
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6H
1H
1H
1H
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b.
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Ch 2: Oxidation and Red x M IR Spectrum Table
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Carbon-13 NMR Spectro X
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6H
Time left 0:58:49
1H
1H
1H
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C.
d.
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Question 5
How many of the IR spectra below come from compounds that contain carboxylic acids?
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HAVENUHBERI-
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TRANSMETTANCET1
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Carbon-13 NMR Spectro X
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TRANSHETTANCE11
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TRANSMITTANCET 1
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HAVENUMBERI –
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HAVENUHBERI-
O
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Ch 2 : Oxidation and Red * |
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Interpreting IR Specta: A X
Carbon-13 NMR Spectro X
S SOLUTION: Organic Che X
GS Final Exam (page 6 of 13 X
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Question 6
When a sample of the compound below is analyzed by mass spectrometry, the molecular ion will appear at m/z :
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40
You should also expect to see significant peaks at
and
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Question 6
When a sample of the compound below is analyzed by mass spectrometry, the molecular ion will appear at m/z =
A
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and
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Ch 2 : Oxidation and Red * |
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GS Final Exam (page 6 of 13 X
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Question 6
When a sample of the compound below is analyzed by mass spectrometry, the molecular ion will appear at m/z =
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Question 7
You have an organic acid, organic base, and a neutral organic compound all together in a solid mixture. What steps would you take, in order,
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To the combined aqueous extracts, add 6M HCl(aq) until the solution is acidic.
To the combined aqueous extracts, add 6M NaOH(aq) until the solution is basic.
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Dry the solution in the beaker with sodium sulfate, filter, and evaporate off the solvent.
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3.
4.
To the combined aqueous extracts, add 6M HCl(aq) until the solution is acidic.
To the combined aqueous extracts, add 6M NaOH(aq) until the solution is basic.
Dry the solution in the beaker with sodium sulfate, filter, and evaporate off the solvent.
Add 3M HCl(aq) and shake and vent, then transfer aqeous phase to a separate flask. Repeat two times.
Rinse the organic phase with brine and transfer to a beaker.
Add 3M NaOH(aq) and shake and vent, then transfer aqeous phase to a separate beaker. Repeat two times.
Dissolve the crude solid in ether and place in separatory funnel.
Filter to collect the solid.
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Question 8
In the acylation of ferrocene experiment, some diacetylferrocene was formed as a biproduct. Where does the second actyl group get added?
Explain why it is added to your chosen position in 30 words or less.
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3 Fe
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ferrocene
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I
Ff
TA
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C ?
The second acyl group will be added on position,
(1, 2, 3, or 4) because:
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Question 9
Consider the reaction below. If the bromine drawn in black is added first to the alkene, what is the major product of the reaction?
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D
Diphenylacetylene was synthesized in lab this quarter. The IR spectrum did not show any C-C triple bond absorption bands. Which of the
following statements is true?
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Question 9
Consider the reaction below. If the bromine drawn in black is added first to the alkene, what is the major product of the reaction?
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A
B
C
D
Diphenylacetylene was synthesized in lab this quarter. The IR spectrum did not show any C-C triple bond absorption bands. Which of the
following statements is true
the absence of the absorption band indicates that reaction did not work
there should not be a C-C triple bond abosrption band in the IR spectrum
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Question 10
A student is performing the aldol condensation below. The student’s table of reagents is also shown below. How many equivalents of the
aldehyde did the student use? Submit your answer to 2 decimal places.
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Reagent MW (g/mol) Density (g/mL) Vol Used (mL) Equiv
Cyclohexanone 98.14 0.948
0.3
1.0
Benzaldehyde 106.12 1.04
0.56
?
Answer:
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Question 11
HOMO/LUMO gaps. This will cause the molecule to absorb
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Moecules with smaller amounts of electron delocalization will have
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shorter || longer
nucleophile electrophile
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Question 12
Which compound is responsible for the 1H-NMR spectrum below?
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In Grignard reagent with bromobenzene and acetophenone, how would the reaction change if a student used ethanol as the solvent rather
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than diethyl ether’
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Dihydropyridines :
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benzene would be the isolated product
ethylbenzene would be the isolated product
the product would be unchanged, but the reaction rate would increase
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In Grignard reagent with bromobenzene and acetophenone, how would the reaction change if a student used ethanol as the solvent rather
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than diethyl ether?
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Dihydropyridines are ✓
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priveledged structures
pharmacophore
How can we change the synthesis of the dihydropyridines we made so that the product would be an effective calcium channel blocker?
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In Grignard reagent with bromobenzene and acetophenone, how would the reaction change if a student used ethanol as the solvent rather
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than diethyl ether?
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Dihydropyridines are
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they tend to be biologically active and their biological target depends on what else is around them in the molecule
they have the necessary bonding interactions to hit the enzyme
m channel blocker?
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In Grignard reagent with bromobenzene and acetophenone, how would the reaction change if a student used ethanol as the solvent rather
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than diethyl ether?
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change the aldehyde we
change the beta-keto ester
change the amine
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When a sample of the compound below is analyzed by mass spectrometry, the molecular ion will appear at m/z =
A
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and
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When a sample of the compound below is analyzed by mass spectrometry, the molecular ion will appear at m/z =
A
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You should also expect to see significant peaks at
an
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Consider the reaction below. If the bromine drawn in black is added first to the alkene, what is the major product of the reaction
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А.
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B
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D
Diphenylacetylene was synthesized in lab this quarter. The IR spectrum did not show any C-C triple bond absorption bands. Which of the
following statements is true?
there should not be a C-C triple bond abosrption band in the IR spectrum
Please put an answer in each box.
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AUG
5
28
GIU 7 A
Tai do
280
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