231L Alkene Addition TEMPLATE
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NEW TEMPLATE: 231L Alkene Addition
Pre-lab Questions
Procedure
1.
(10 pts) Write a bullet list outline for the procedure.
Setup reflux 2.
(5 pts) Write
a brief summary of the key safety concerns specific for this experiment.
Mechanism
3.
(25 pts) The first step in the bromination of an alkene is the nucleophilic attack of the alkene on the bromine. This attack causes the loss of the bromide ion leaving group. A bridged bromonium ion is formed. This is shown below with cyclpentene.
Draw the first step in the mechanism for today’s reaction between trans
-cinnamic acid and bromine. 4.
The next step for bromination of an alkene is nucleophilic attack of bromide on the bromonium ion. The bromide attacks one corner of the bridge as shown below.
a.
(4 pts) Given that syn addition would give both bromines on the same side and anti addition would give bromines on opposite sides, what type of addition is halogenation of alkenes? b.
(20 pts) Draw this step for the bromination of cinnamic acid. 5.
(8 pts) Another aspect of bromination that must be considered is stereochemistry. For the bromination of trans-2-
butenoic acid, two chiral centers are formed in the product (indicated by stars).
Due to the presence of chiral centers, four different stereoisomers are possible: (Solid wedge mean bond is coming out of paper towards you. Dashed wedge means bond is going out the back of the paper.)
However, only two products are observed. Which two of the above products would be consistent with the addition mechanism of bromination of alkenes? Circle these products above. 6.
(13 pts) Draw the product for the bromination of trans
-cinnamic acid (do not use wedges and dashes, yet) and put a star by each chiral carbon. 7.
(32 pts) Draw the four possible stereoisomers for the bromination of trans
-cinnamic acid using wedges and dashes. 8.
(8 pts) Which two of the stereoisomers you drew would be consistent with the addition mechanism of bromination of alkenes? Circle the products you would expect in the bond line structures you drew above.
9.
(25 pts) Draw a reaction scheme today’s reaction. Include stereochemistry and all possible products consistent with mechanism.
Amount to Use
10.
(5 pts) Calculate how much cinnamic acid to use based on moles. The following table guides you in this. Reactant
trans-
cinnamic acid
Moles
0.01 mol
MW
148.16
g/mol
Amount Fill in
Data and Observations
1.
(5 pts) Mass of roundbottom flask. 22.337g 2.
(5 pts) Mass of cinnamic acid and flask________
3.
(5 pts) Mass of cinnamic acid. 1.484g 4.
(5 pts) Mass of watch glass 27.31g
5.
(5 pts) Mass of product on watch glass 29.49 g
6.
(5 pts) Mass of product _____________ 7.
(5 pts) Product melting point 268C – 275C 8.
(20 pts) Insert a photo of your FTIR spectrum for your product. Draw the structure of your product
on or near the spectrum. Label the peaks in the spectrum which correspond to functional groups in your product. The FTIR spectrum of cinnamic acid is provided below for comparison.
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9.
(20 pts) As you are performing the synthesis, record any issues you had or what you could have done differently in order to get better results.
Analysis and Application Questions Analysis
1.
(15 pts) Calculate the percent yield. Show your work.
Reactant
Product
Cinnamic acid
2,3-dibromo-3-
phenylpropanoic acid
Mass Fill in
Fill in
MW
148.16 g/mol
307.97 g/mol
Moles Fill in
Fill in
FTIR Cinnamic
Acid
Since one mole of substrate yields one mole of product:
Percent Yield = (mole product /mole reactant) x 100 2.
(20 pts, 10 pts for specifically explaining how each type of data supports claim) Was your synthesis of 2,5-dichloro-2,5-dimethylhexane successful? Explain. Use your FTIR, and melting point data as evidence in your explanation. Remember that you need to be specific when using data as evidence of your claim of success or lack of success. If you were unsuccessful, use the issues you recorded while doing the experiment to make a specific suggestion for what you would do differently to get better results. Application
3. (25 pts) Complete each reaction. Show the stereochemistry of each product.
4.
A variety of different species can be added across an alkene double bond which makes alkenes incredible useful in industry. For example, ethene derived from petroleum is used to produce PVC. One industrially important synthesis is the addition of hydrogen, H
2
, across alkene double bonds. This is accomplished using hydrogen gas and a catalyst such as nickle. Let’s look at this reaction using the starting material used in this experiment, cinnamic acid:
a.
(5 pts) Unlike Bromine, hydrogen is added across the double bond in a syn fashion. The above product is drawn without showing stereochemistry. Redraw the product showing a syn addition of hydrogens by using wedges and dashes. b.
(5 pts) Considering stereochemistry, how many products will result from this reaction? Hint: Does the product have the same chiral carbons as the bromination product?
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Related Documents
Related Questions
ciple Attempts Not allowed. This test can only be taken once.
ce Completion Once started, this test must be completed in one sitting. Do not leave the test before clicking Save and Submit
This test does not allow backtracking. Changes to the answer after submission are prohibited.
emaining Time: 52 minutes, 44 seconds.
Question Completion Status:
A Moving to the next question prevents changes to this answer.
Question 2
Reaction of arenediazonium salts with aryl benzene give....
o Aryl halied
Benzonitrile
Phenole
Azo dayes
A Moving to the next question prevents changes to this answer.
P Type here to search
1HUAWE
F1
F2
F3
F4
F5
F6
F7
%23
24
%
&
2
5
6.
7
8.
Q
W
E
T
Y.
us
A
H.
1S
C,
Z
C
VI
B U
DI
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4. Circle the electrophilic and nucleophilic atoms in each substitution reaction below.
Provide the neutral organic product; where a stereocenter is created, use a wavy bond
to indicate a mixture of configurations or wedges/dashes for stereospecific reactions.
Also, provide the dominant reaction mechanism (Sn2 or SN1) somewhere in each box.
A.
Br
NaSEt
DMF
В.
ELOH
C.
.SO2NHNA
Cl
+
D.
NaH
Br-
HO,
DMF
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How does gold help to catalyze the reaction in the gold catalysis experiment?
It deprotonates the methanol, making methanol a better nucleophile.
оа.
o b. It donates electron density to the alkyne, making the alkyne a better nucleophile.
О с.
It coordinates to the methanol, making methanol a better nucleophile.
o d. It coordinates to the alkyne, making the alkyne a better electrophile.
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Which is/are NOT TRUE about bimolecular nucleophilic substitution reactions?
Select one or more:
1. A carbocation intermediate is formed.
2. A strong nucleophile displaces a halogen atom in a concerted mechanism.
3. Presence of polar aprotic solvents promotes this reaction.
4. Methyl halides react faster than secondary alkyl halides.
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Question 20
In a unimolecular elimination (E1) reaction, the correct order of mechanistic steps is
А.
dissociation of the leaving group, then deprotonation at the ß position.
simultaneous dissociation of the leaving group and deprotonation of the B position.
association of the nucleophile/base, then dissociation of the leaving group.
deprotonation at the B position, then dissociation of the leaving group.
В.
C.
D.
В
O A
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Electrophilic aromatic substitutions proceed in two stages.
1. Attack of the aromatic ring on the electrophile.
2. Regeneration of the stable aromatic system by loss of a positively charged unit, usually a proton.
Br
Br₂/FeBr3
Draw one resonance structure for the intermediate formed when the electrophile is attacked by benzene in the reaction above.
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
• Do not include lone pairs in your answer. They will not be considered in the grading.
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Circle the electrophilic addition reaction(s) that form(s) a three-membered
ring intermediate.
a. Addition of hydrogen halides
b. Acid-catalyzed addition of water
c. Acid-catalyzed addition of alcohols
d. Hydroboration-oxidation
e. Addition of a halogen
f. Addition of a peroxyacid
g. Ozonołysis of alkenes
h. Addition of hvdrogen
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Can you match best nucleophile / conditions from the list that will give a successful hydrolysis reaction for each electrophile? (there's one best nucleophile / conditions for each electrophile)
<List for Nucleophile / condition>
a. LiAlH4; hydronium work-up
b. PCC
c. NaH
d. CrO3
e. HOEt
f. H3O+ or OH-
g. H2O
h. NaBH4;hydronium work-up
Electrophile
1. Acid chloride
2. Acetic anhydride
3. Ester
4. Amide
I'm asking again on bartleby because pther tutor gave me the right answer because I think I didn't make my question clear enough.
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13
saved
out of
on 14
r saved
out of
Given the following substitution reaction, what would the effect be of changing the solvent from DMF to CH₂OH? (see
NOTE)
*NOTE:
DMF
-
NaOCH3
H-C-N(CH3)2
OCH 3
Select one:
OA. There would be no effect on the reaction rate.
OB. The rate of the reaction would increase.
OC. The rate of the reaction would decrease.
Clear my choice
+
Na Br
In substitution reactions, (CH3)3C-I reacts at the same rate with Brand CI even though Br is a more reactive nucleophile
than Cl. Why?
max
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5. Predict the major product of the following reactions.
A.
+ HBr
В.
HBr
C.
+ H Br
6. Use curved arrows to show to show the mechanism of the reaction C above.
Nucleophiles and Electrophiles
7. Label the electrophile and nucleophile in each step of the mechanism for question 6.
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For each horizontal row of substituted benzenes, indicate
a. the one that is the most reactive in an electrophilic aromatic substitution reaction. b. the one that is the least reactive in an electrophilic aromatic substitution reaction. c. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction.
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K
Question Completion Status:
QUESTION 6
Select the missing reagent for the reaction seen below:
Cl₂/AIC13
C1₂
ⒸCl₂/FeCl3
HCI
QUESTION 7
Salert the miceina raanant from tah raaction echama caan haloue
Click Save and Submit to save and submit. Click Save All Answers to save all answers.
mercy.blackboard.com
F
Support ?
CI
Save All Answ
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What are the errors in the following answer?
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Payalben
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LOH
NaOH
`N'
(S)
H20
'N'
ČI
This nucleophilic substitution occurs with rearrangement. Draw curved arrows to show the movement of electrons in the following step of the reaction mechanism.
Arrow-pushing Instructions
OH
:OH
N.
H.
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Show how you might synthesize this compound from an alkyl bromide and a nucleophile in an S№2 reaction.
N3
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
• Only draw the reactants. Separate multiple reactants using the + sign from the drop-down menu.
• If there is more than one possible combination of alkyl bromide and nucleophile, draw only one combination.
• Do not include counter-ions, e.g., Na+, I, in your answer.
90-85
TAYY
?
ChemDoodle
O
OO.
#[ ] در
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12
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Choose all correct statements.
1. Gilman reagents react with alkyl halides, including vinyl and
aryl halides.
2. Grignard reagents react with alkyl halides, including vinyl and
aryl halides.
3. Deprotonation of an alcohol group forms an oxonium
intermediate.
4. Whenever a neutral nucleophile attacks, a proton transfer
step follows.
5. An alcohol that is chiral at the a-carbon will undergo
inversion of absolute configuration when it is converted into
an alkyl tosylate.
C
1
2
3
4
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5. In an organic reaction, which of the following is most likely to function as only a nucleophile?
a. BF3
b. (CH3)2CH2NH2
с. Fe2+
d. CH3CH2S¯
e. both a and c
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Draw the structure of the alkyl bromide and the nucleophile that will react in an Sy2 reaction to give the product shown.
CN
Alkyl bromide + Nucleophile
H3C
• You do not have to consider stereochemistry.
Separate multiple reactants using the + sign from the drop-down menu.
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Step 4a: Classify step.
The target product is present, but the reaction is not over. The ethoxide ion has been regenerated.
:0:
:0:
What is the key process in the next step of the mechanism?
proton transfer
formation of a o bond between nucleophile and electrophile
loss of a leaving group
carbocation rearrangement (e.g., methyl or hydride shift)
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- 5. Predict the major product of the following reactions. A. + HBr В. HBr C. + H Br 6. Use curved arrows to show to show the mechanism of the reaction C above. Nucleophiles and Electrophiles 7. Label the electrophile and nucleophile in each step of the mechanism for question 6.arrow_forwardFor each horizontal row of substituted benzenes, indicate a. the one that is the most reactive in an electrophilic aromatic substitution reaction. b. the one that is the least reactive in an electrophilic aromatic substitution reaction. c. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction.arrow_forwardK Question Completion Status: QUESTION 6 Select the missing reagent for the reaction seen below: Cl₂/AIC13 C1₂ ⒸCl₂/FeCl3 HCI QUESTION 7 Salert the miceina raanant from tah raaction echama caan haloue Click Save and Submit to save and submit. Click Save All Answers to save all answers. mercy.blackboard.com F Support ? CI Save All Answarrow_forward
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