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Download the file written "chem 122 lab manual". This will help you to see what is required from the lab.this file contains questions you need to answer.
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steps required do the lab
1) indicate the start time in your lab book before the start of any lab
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Running Head: REACTIONS OF HYDROCARBONS
Lab Report: Experiment 3
Reactions of Hydrocarbons
Student Name
Instructor
Course Name:
Course Code
University
Date
REACTIONS OF HYDROCARBONS
2
Reactions of Hydrocarbons
Part A: Hydration
Organize the data for your reactions in a data table like the following:
Starting material(s) (Name or Solvent, reagent
structure, Rf value)
Product(s) (Name or
structure, Rf value)
1-methycyclohexene, (0.74)
H2O, H2SO4
1-methycyclo-hexanol,
(0.48)
Styrene (0.75)
H2O, H2SO4
1-phenyl ethanol,
(0.41)
Time of Reaction
(minutes)
70 minutes
100 minutes
1. Write a 3-step arrow pushing mechanism for the formation of 1-methyl-cyclohexanol:
i.
The first step is the protonation of 1-methycyclohexene by the catalyst (H2SO4) to form a
carbocation.
ii.
In the second step, the water molecules attack the carbocation
iii.
In The last step, the carbocation is deprotonated to form the alcohol 1-methylcyclohexanol:
2. Which reaction proceeds through the more stable carbocation? Briefly explain.
REACTIONS OF HYDROCARBONS
3
Styrene hydration proceeds with the more stable carbocation than 1-methylcyclohexene
which produces an unstable high energy species. this is because the more a compound is
substituted the more stable the carbocation. Also, it is important to note that both cations
produced as intermediate have a secondary structure but styrene with the benzylic ring can
form a resonance from the electrons from the aromatic ring which contributes to its stability
Part B: Hydrochlorination
Organize the data for your reactions in a data table like the following:
Starting material(s)
(Name or structure,
Rf value)
Solvent, reagent
(Name or structure,
Rf value)
1-hexene, (0.75)
3. 3-diethyl-1butene, (0.65)
Diethyl ether, Hcl
2-chlorohexane, (0.62)
Time of
Reaction
(minutes)
120 minutes
110 minutes
Diethyl ether, Hcl
2-chloro-3,3-dimethylbutane,
(0.68)
1. Write a 2-step arrow pushing mechanism for the formation of 2-chlorohexane:
2. Provide a brief explanation for the unexpected product noted in your second reaction, targeting 2chloro-3,3-dimethylbutane. Use your observations as evidence.
Part C: Bromination
Starting material(s)
(Name or structure,
Rf value)
Solvent,
reagent
1-methyl-cyclohexene, diethyl ether,
(0.73)
BR2
3,3-dimethyl-1butene, (0.70)
diethyl ether,
BR2
(Name or structure,
Rf value)
Time of Reaction
(minutes)
10 minutes
1,2-dibromo-1-methylcyclohexane,
(0.68)
10 minutes
1,2-dibromo-3,3-dimethylbutane,
(0.64)
REACTIONS OF HYDROCARBONS
4
1. Provide a brief explanation for the regioselectivity of the product noted in your first
reaction, targeting 1,2- dibromo-1-methylcyclohexane.
The product formed was trans-1,2-dibromo-1-methylcyclohexane, which means the Br atoms
were attached on the opposite faces of the C=C double bond, which means the product formed is
regioselective.
2. Provide a brief explanation for the differences noted between the bromination of 3,3dimethyl-1-butene and the hydrochlorination of 3,3-dimethyl-1-butene.
In the bromination of 3,3-dimethyl-1-butene, the reaction is regioselective because the Br atoms
are attached from the opposite face of the C=C (trans-conformation), where a Br+ is formed as a
result, which is an intermediate. In hydrochlorination on the other hand, the Cl is added to the most
substituted (fewer H atoms) at the double bond, and both the Cl and H atoms are attached to the C
from the same side unlike in bromination (Cis- conformation).
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Start time:7:52
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Repeat Reaction: Reaction Start time: 8:05, Observation: two large spots observed on
reaction path.
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2nd TLC observation: The furthest spot is larger,followed by the second and the third which has
moved short distance is the smallest.
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In the third TLC plate, the furthest spot on thereaction lane has grown larger than before while
the one close to base line is diminishing.
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4th TLC the reaction is not yet over, there arestill 3 spots on the reaction lane
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5th TLC plate, the reaction is complete and onelarge spot is observed on reaction lane
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Confirmation Test: Upon confirming the reactionon the flask using TLC, it showed that the flask
contained the same product produced in thereaction. This means the synthesis was
successful.
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Reaction between acetic acid and Methanol:Start time: 8:49, 1st TLC plate showed two large
spots o the reaction lane
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2nd TLC plate: Three spots are seen on thereaction lane. The middle spot is larger than the
other two.
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3rd TLC plate. The three spots persist on thereaction lane but the sizes changed. The spot
which moved short distance has began todiminish while the furthest one is growing
larger, The middle spot is also becoming smaller.
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4th TLC plate: The furthest spot growing largerthe one which moved short distance
diminishing.
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5th TLC plate: The furthest spot continue togrow as the others diminish.
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The reaction ended on the 8th test.
Upon testing for the final product, the TLC platedid not show any spot. For unknown reason.
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Reaction Between Butanoic Acid and Ethanol
Start time: 9:23
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Observations: 1st TLC plate had two large spotson the reaction lane.
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