lab report

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wezbun

Science

Seattle Central College

Description

go to this website https://gibbs.beyondlabz.com/ you need to use this credentials

username: jrmoha

pass: @4119Moha

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.

the objective of this assignment to use this website to do labs then submit your lab report with you lab book. You need to save your lab book on beyond labs.

Download this file from dropbox https://www.dropbox.com/s/r4x3re7c3reu6nu/Lecture....

this video file will guide you through how to do the experiment. And the important steps required of you.

steps required do the lab

1) indicate the start time in your lab book before the start of any lab

2) save your tlc

3) and later when you finish your lab save your lab as a pdf to your computer

4) do the lab report questions

5) upload all the files( the lab report and the lab book)

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Experiment 3 Reactions of Hydrocarbons Purpose: This experiment explores a variety of electrophilic alkene addition reactions by targeting a specific series of compounds, observing the differences in how the syntheses proceed. Background Information: Reaction with Water. Alkenes will not react with water alone, the presence of an acid catalyst (H 2SO4) is required. The reaction is the addition of a hydrogen to one side of the double bond, hydroxide to the other: H2O OH H2SO4 Heat may or may not be required, depending on the strength of the carbocation intermediate. Where different products are possible, the product that results from the most stable carbocation intermediate is favored. TLC is necessary to follow the course of the reaction. Reaction with Hydrochloric acid. This reaction is the addition of the elements of hydrochloric acid to the carbons of the multiple bonds: HCl Cl diethyl ether Where different products are possible, the product that results from the most stable carbocation intermediate is favored. The reaction may proceed at room temperature but will take place more efficiently with heat. TLC is necessary to follow the course of the reaction. 10 Reaction with Bromine. Alkenes react rapidly with bromine, often at room temperature. The reaction is the addition of the elements of bromine to the carbons of the multiple bonds: Br2 diethyl ether Br Br The bromine solution is orange; the product that has the bromine atoms attached to carbon is colorless. Thus, a reaction has taken place when there is a loss of color from the bromine solution and a colorless solution remains. This may be confirmed by observing a different spot on the TLC. The size of the bromine may impact the specific product seen. Procedure: Launch the BeyondLabz program. When the client opens, select Organic Synthesis . Select Alkene Hydration from the screen to the right. Part A: Hydration The target compounds that you should synthesize for part A are 1-methyl-cyclohexanol and 1-phenyl ethanol. 1. Identify the appropriate starting materials required to synthesize 1-methyl-cyclohexanol from the available reagents on the stockroom shelf and add them to the round bottom flask. Now add water (H 2O) as a solvent and drag the flask to the stir plate on the lab bench. 2. From the group of reagents found on the lab bench, select the correct reagent to synthesize the target compound and add it to the flask on the stir plate. Now attach the heater, condenser, and N 2 gas to the round bottom flask so the reaction mixture can be heated. 3. Start the reaction (note reaction start time) by clicking on the Stir button on the front of the stir plate. You should be able to observe the reaction mixture stirring in the flask, the contents of the flask should be displayed on the screen to the right. Monitor the progress of the reaction using TLC measurements as necessary until the product has formed and the starting materials have been consumed. You can advance the laboratory time using the clock on the wall. Keep track of your data in your Lab Book. 4. When the reaction is complete (note reaction stop time), work up your reaction by first dragging and dropping the separatory funnel on the flask and then adding H2O to the funnel. Extract the organic layer in the funnel by clicking on the top layer and dragging it to the cork ring on the lab bench. Your target compound should now be in this flask. Examine the product to determine the location of the new functionality. If something happen o don e pec ake no e Yo ma ha e mi ed ome mall de ail in he p oced e fail e o add H2SO4 of en e l in fo ma ion of black a af e one da !) or you may have discovered something new. Repeat steps 1-4 targeting 1-phenyl ethanol. 11 Part B: Hydrochlorination The target compounds that you should synthesize for part B are 2-chlorohexane and 2-chloro-3,3dimethylbutane. 1. Identify the appropriate starting materials required to synthesize 2-chlorohexane from the available reagents on the stockroom shelf and add them to the round bottom flask. Now add diethyl ether as a solvent and drag the flask to the stir plate on the lab bench. Steps 2-4 proceed as in Part A. Repeat steps 1-4 targeting 2-chloro-3,3-dimethylbutane. Pay close attention to the final product. Any surprises? Part C: Bromination The target compounds that you should synthesize for part C are 1,2-dibromo-1-methylcyclohexane and 1,2dibromo-3,3-dimethylbutane. 1. Identify the appropriate starting materials required to synthesize 1,2-dibromo-1-methylcyclohexane from the available reagents on the stockroom shelf and add them to the round bottom flask. Now add diethyl ether as a solvent and drag the flask to the stir plate on the lab bench. Steps 2-4 proceed as in Part A, except bromination usually takes place just fine at room temperature. The expected color change provides a visual clue as to when the reaction is done; back this up with TLC data. Pay close attention to the structure of the final product. Repeat steps 1-4 targeting 1,2-dibromo-3,3-dimethylbutane. Open your Lab Book and click the Export To PDF button to download your Lab Book as a pdf file; submit this with your lab report. 12 Lab Report Answer all questions on separate notebook paper or a different computer file and upload to Canvas by next Wednesday evening. Include the pdf file of your BeyondLabz Lab Book with your report. Part A: Hydration Organize the data for your reactions in a data table like the following: Starting material(s) (Name or structure, Rf value) Solvent, reagent Product(s) (Name or structure, Rf value) Time of Reaction (minutes) 1. Write a 3-step arrow pushing mechanism for the formation of 1-methyl-cyclohexanol: 2. Which reaction proceeds through the more stable carbocation? Briefly explain. 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 Product(s) (Name or structure, Rf value) 13 Time of Reaction (minutes) 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 2-chloro-3,3dimethylbutane. Use your observations as evidence. Part C: Bromination Organize the data for your reactions in a data table like the following: Starting material(s) (Name or structure, Rf value) Solvent, reagent Product(s) (Name or structure, Rf value) Time of Reaction (minutes) 1. Provide a brief explanation for the regioselectivity of the product noted in your first reaction, targeting 1,2dibromo-1-methylcyclohexane. 2. Provide a brief explanation for the differences noted between the bromination of 3,3-dimethyl-1-butene and the hydrochlorination of 3,3-dimethyl-1-butene. 14
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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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