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Chem 51LB Experiment 6 Report
Scaffold
Unknowns Separation Project
Instructions
Report scaffolds are provided to help you learn how to write about the experiments you
conduct. Now you will be responsible for providing your own experiment-specific
questions and answering them. General questions are still provided here for
reference. Type your experiment-specific questions and answers into a separate
document. Label each section of your document and number your questions. The
document containing your responses should not exceed a total of five pages. Mechanism
drawings may be attached at the end of your document and do not count toward the five
page limit.
As you go through the process of generating and responding to your questions, think
about how you would convert your answers into paragraphs that flow well for an actual
report. You will begin writing lab reports in Chem 51LC!
Post-Lab Report Format: MUST BE TYPED IN WORD OR A SIMILAR PROGRAM,
NOT AN ELN PAGE! Times New Roman; 12 pt. font; double spaced; 1” margins; no more
than 5 pages; use 3rd person passive voice only (For example, “We dissolved the white
solid in 10 mL of hot water,” should be written as, “The white solid was dissolved in 10
mL of hot water.”). Include your name, student ID number, and lab course code. This
format is NOT OPTIONAL and TA’s will remove points for failure to follow these
instructions.
Purpose/Introduction
General Questions:
What were we trying to accomplish with this experiment? How did we plan to accomplish
this? The purpose of an experiment is not simply to introduce a student to a technique
or reaction!
Theory
General Questions:
Assume you are writing for another student who has taken organic chemistry before but
might have forgotten some of the details of reactions and lab techniques. What
information about the reaction and/or techniques being used in this experiment would you
need to remind them of to make sure they understand what you did, why you did it, and
what the results mean? If there is a reaction involved you should include a
mechanism. Drawings of the mechanism should be attached.
Results
General Questions:
What important data were obtained in this experiment? The data provided in this section
should relate to the purpose(s) of the experiment, but you do not need to point out the
connections here. Do not explain your results yet. Just provide them in an organized
format. Don’t forget to include any assigned unknown number! You should include a
table to organize your data in addition to sentences.
Discussion and Error Analysis
General Questions:
How do the data obtained relate to the purpose(s) of the experiment? How do you know
the identity of the product and/or unknown? Do the results make sense? What
conclusions can you draw from the data? What conclusions can you NOT draw from the
data? (Note that although you are provided with distinct, individual questions here,
sometimes the answers to these questions might overlap with each other. That’s ok! In
a lab report you would need to decide how to tie these answers together.)
Conclusions and Future Experiments
General Questions:
How would you summarize your results and analysis in 1-2 sentences? In other words,
what is it that you want the reader to remember after having read your paper?
What questions remain unanswered? What questions were raised by your results and
analysis?
12/23/18
Chem 51LB SS1 2019 – Bin Zhang
Exp 6: Unknowns Separation Project/PreLab/InLab – Part 1
PDF Version generated by
Bin Zhang
on
Jul 19, 2019 @08:42 PM PDT
Table of Contents
PreLab/InLab – Part 1 ………………………………………………………………………………………………………………………………………………………………………………………………………………… 2
Exp 6: Unknowns Separation Project/PreLab/InLab – Part 1
2 of 5
PreLab/InLab – Part 1
PAGE LOCKED – Assignment has been submitted
Bin Zhang Jul 19, 2019 @08:42 PM PDT
Note: You cannot edit this assignment after it has been submitted.
Assignment #
7
Name
PreLab/InLab Wk 7
I worked in a group with
Bjazevic, Karina; Boos, Drake; Gewarges, Christine; Kim, Anastasia
The work for this assignment is in
My notebook
Submitted on Jul 19, 2019 @08:42 PM PDT
Bin Zhang Jul 19, 2019 @04:51 PM PDT
Objective
Bin Zhang Jul 19, 2019 @06:45 PM PDT
In this week lab, we going to figure out the unknown compound structure from NMR spectrum provide by stock room. After figure out the major and
minor compound in the mixture, using TCL test to testify the hypothesis of the NMR result with the standard solution. The determine the separate
method by the property of the compound of two compounds through recrystallization or extraction.
Bin Zhang Jul 19, 2019 @06:46 PM PDT
Chemical Table
Bin Zhang Jul 19, 2019 @07:05 PM PDT
View
Copy to Clipboard
Show 10
Export to File
Show / hide columns
entries
Search:
Formula
FW
(g/mol)
physical
state
2’-bromoacetanilide
CH3CONHC6H4Br
214.06
solid
4’-bromoacetanilide
CH3CONHC6H4Br
214.06
solid
benzhydrol
C13H12O
184.23
solid
biphenyl
C12H10
154.21
solid
caffeine
C8H10N4O2
194.19
solid
p-acetophenetidide
C12H17NO2
207.27
solid
phenylacetic acid
C8H8O2
136.15
solid
propyl 4-hydroxybenz…
C10H1203
180.20
solid
triphenylmethane
C19H16
244.33
solid
Chemical Name
Showing 1 to 9 of 9 entries
Mass
(g)
moles
Volume
other
constants
Concentration
First
Previous
1
Next
Last
Exp 6: Unknowns Separation Project/PreLab/InLab – Part 1
3 of 5
Bin Zhang Jul 19, 2019 @07:12 PM PDT
GHS TABLE
Bin Zhang Jul 19, 2019 @07:12 PM PDT
View
Copy to Clipboard
Show 10
Export to File
Show / hide columns
entries
Search:
Signal
Word
GHS
Symbol
1
2-bromoacetanilide
Warning
Irritant
eye/skin damage/irrit…
2
4’-bromoacetanilide4…
none
None
none
0
benzhydrol
none
None
none
biphenyl
Warning
Irritant
caffeine
Danger
Poison
p-acetophenetidide
Warning
Phenylacetic acid
Propyl 4-hydroxyben…
triphenylmethane
Chemical Name
Showing 1 to 9 of 9 entries
Minimize
Risk 1b
GHS
Symbol
2
wear goggles, lab co…
none
None
none
none
none
None
none
0
none
none
None
none
eye/skin damage/irrit…
2
none
none
Poison
aquatic to
oral toxicity
4
none
none
None
none
Poison
oral toxicity
4
none
none
None
none
none
Irritant
eye/skin damage/irrit…
2
none
none
None
none
none
None
aquatic toxicity
0
none
none
None
none
none
None
none
0
none
none
None
none
Hazard 1
Hazard
#1
Minimize Risk 1a
First
Previous
1
Next
Hazard
Last
Exp 6: Unknowns Separation Project/PreLab/InLab – Part 1
4 of 5
Bin Zhang Jul 19, 2019 @07:13 PM PDT
EQUIPMENT
Bin Zhang Jul 19, 2019 @07:22 PM PDT
1.beaker
2. vial
3. TLC plate
4. Vacuum filter flask
5. Hirsch funnel
6. melting point capillary tube
7. Mel-temp
8. TLC capillary tube
Exp 6: Unknowns Separation Project/PreLab/InLab – Part 1
5 of 5
Bin Zhang Jul 19, 2019 @07:22 PM PDT
Procedure
Bin Zhang Jul 19, 2019 @08:41 PM PDT
1. obtain unknown compound from TA and identify the NMR result provided by TA
Observation: we got the number #54 of unknown compound and the unknown compound is white powder solid. Through the NMR spectrum, we
speculate the major compound in the 4-bromoacetanilide and the minor compound is 2-bromoacetanilide.
2. Do a TLC test compare with the unknown compound and the possible compounds provide in the lab. Then run a melting point test of the unknown
compound.
Observation: we first run a 7:3 of Hexanes/ethyl acetate test of TLC test. dissolve a small amount of unknown compound in acetone. Spot the
unknown compound on the left of the TLC, 4-bromoacetanilide in the middle and on right is 2-bromoacetanilide. The result from 7:3 show all the spot stuck at
bottom line so we change the solvent to 5:5 of hexane and ethyl acetate solution and the Rf result is below.
unknown spot1
Rf 0.38
unknown spot 2
4-bromoacetanilide
2-bromoacetanilide
0.68
0.35
0.62
The melting point of the mixture is 118.8-140.3 °C
3. Decide what the separate method to use to separate unknown compound either by acid-base extraction or recrystallization
After separation, do a melting point test and a mixture melting point test.
1) acid-base extraction
dissolve the mixture into either diethyl ether or dichloromethane and fill into a sup funnel, and add suitably acid or base aquation into the
funnel and fully mix two solutions. Then separate two layers into two separate containers and use the opposite of the ph range acid
or base to the aquatic layer. Then filter the aquatic layer and evaporate the organic layer.
2) recrystallization
dissolve the mixture in hot ethanol drops by drops until all the solid solve then add hot water until precipitate appears in the solution. Then wait until
the solution turns to room temperature do an ice bath for 15 mins. After that, vacuum filter the solution for 15 mins and in the end using ice water to
wash the precipitate
Observation: We decide to run recrystallization to separate two compounds in the mixture since two compounds have the same chemical properties.
The 4-bromoacetanilide solid from the stock room is brown and orange color shiny solid powder. The solid we got from the recrystallization is white fluffy solid
powder.
the crude solid of the mixture is 0.477g
after recrystallization: 0.374g
The melting point of the recrystallization production is 165.4-170.8 °C
After the recrystallization, we did another TLC testing of our production with 4-bromoacetanilide and 2-bromoacetanilide
production #1
Rf 0.636
#2
4-bromoacetanilide
2-bromoacetanilide
0.333
0.364
0.667
On the TLC testing, there are still two spots on the recrystallization production but the top one is really tiny.
Chem 51LB SS1 2019 – Bin Zhang
Exp 6: Unknowns Separation Project/PreLab/InLab – Part 1
PDF Version generated by
Bin Zhang
on
Jul 19, 2019 @08:42 PM PDT
Table of Contents
PreLab/InLab – Part 1 ………………………………………………………………………………………………………………………………………………………………………………………………………………… 2
Exp 6: Unknowns Separation Project/PreLab/InLab – Part 1
2 of 5
PreLab/InLab – Part 1
PAGE LOCKED – Assignment has been submitted
Bin Zhang Jul 19, 2019 @08:42 PM PDT
Note: You cannot edit this assignment after it has been submitted.
Assignment #
7
Name
PreLab/InLab Wk 7
I worked in a group with
Bjazevic, Karina; Boos, Drake; Gewarges, Christine; Kim, Anastasia
The work for this assignment is in
My notebook
Submitted on Jul 19, 2019 @08:42 PM PDT
Bin Zhang Jul 19, 2019 @04:51 PM PDT
Objective
Bin Zhang Jul 19, 2019 @06:45 PM PDT
In this week lab, we going to figure out the unknown compound structure from NMR spectrum provide by stock room. After figure out the major and
minor compound in the mixture, using TCL test to testify the hypothesis of the NMR result with the standard solution. The determine the separate
method by the property of the compound of two compounds through recrystallization or extraction.
Bin Zhang Jul 19, 2019 @06:46 PM PDT
Chemical Table
Bin Zhang Jul 19, 2019 @07:05 PM PDT
View
Copy to Clipboard
Show 10
Export to File
Show / hide columns
entries
Search:
Formula
FW
(g/mol)
physical
state
2’-bromoacetanilide
CH3CONHC6H4Br
214.06
solid
4’-bromoacetanilide
CH3CONHC6H4Br
214.06
solid
benzhydrol
C13H12O
184.23
solid
biphenyl
C12H10
154.21
solid
caffeine
C8H10N4O2
194.19
solid
p-acetophenetidide
C12H17NO2
207.27
solid
phenylacetic acid
C8H8O2
136.15
solid
propyl 4-hydroxybenz…
C10H1203
180.20
solid
triphenylmethane
C19H16
244.33
solid
Chemical Name
Showing 1 to 9 of 9 entries
Mass
(g)
moles
Volume
other
constants
Concentration
First
Previous
1
Next
Last
Exp 6: Unknowns Separation Project/PreLab/InLab – Part 1
3 of 5
Bin Zhang Jul 19, 2019 @07:12 PM PDT
GHS TABLE
Bin Zhang Jul 19, 2019 @07:12 PM PDT
View
Copy to Clipboard
Show 10
Export to File
Show / hide columns
entries
Search:
Signal
Word
GHS
Symbol
1
2-bromoacetanilide
Warning
Irritant
eye/skin damage/irrit…
2
4’-bromoacetanilide4…
none
None
none
0
benzhydrol
none
None
none
biphenyl
Warning
Irritant
caffeine
Danger
Poison
p-acetophenetidide
Warning
Phenylacetic acid
Propyl 4-hydroxyben…
triphenylmethane
Chemical Name
Showing 1 to 9 of 9 entries
Minimize
Risk 1b
GHS
Symbol
2
wear goggles, lab co…
none
None
none
none
none
None
none
0
none
none
None
none
eye/skin damage/irrit…
2
none
none
Poison
aquatic to
oral toxicity
4
none
none
None
none
Poison
oral toxicity
4
none
none
None
none
none
Irritant
eye/skin damage/irrit…
2
none
none
None
none
none
None
aquatic toxicity
0
none
none
None
none
none
None
none
0
none
none
None
none
Hazard 1
Hazard
#1
Minimize Risk 1a
First
Previous
1
Next
Hazard
Last
Exp 6: Unknowns Separation Project/PreLab/InLab – Part 1
4 of 5
Bin Zhang Jul 19, 2019 @07:13 PM PDT
EQUIPMENT
Bin Zhang Jul 19, 2019 @07:22 PM PDT
1.beaker
2. vial
3. TLC plate
4. Vacuum filter flask
5. Hirsch funnel
6. melting point capillary tube
7. Mel-temp
8. TLC capillary tube
Exp 6: Unknowns Separation Project/PreLab/InLab – Part 1
5 of 5
Bin Zhang Jul 19, 2019 @07:22 PM PDT
Procedure
Bin Zhang Jul 19, 2019 @08:41 PM PDT
1. obtain unknown compound from TA and identify the NMR result provided by TA
Observation: we got the number #54 of unknown compound and the unknown compound is white powder solid. Through the NMR spectrum, we
speculate the major compound in the 4-bromoacetanilide and the minor compound is 2-bromoacetanilide.
2. Do a TLC test compare with the unknown compound and the possible compounds provide in the lab. Then run a melting point test of the unknown
compound.
Observation: we first run a 7:3 of Hexanes/ethyl acetate test of TLC test. dissolve a small amount of unknown compound in acetone. Spot the
unknown compound on the left of the TLC, 4-bromoacetanilide in the middle and on right is 2-bromoacetanilide. The result from 7:3 show all the spot stuck at
bottom line so we change the solvent to 5:5 of hexane and ethyl acetate solution and the Rf result is below.
unknown spot1
Rf 0.38
unknown spot 2
4-bromoacetanilide
2-bromoacetanilide
0.68
0.35
0.62
The melting point of the mixture is 118.8-140.3 °C
3. Decide what the separate method to use to separate unknown compound either by acid-base extraction or recrystallization
After separation, do a melting point test and a mixture melting point test.
1) acid-base extraction
dissolve the mixture into either diethyl ether or dichloromethane and fill into a sup funnel, and add suitably acid or base aquation into the
funnel and fully mix two solutions. Then separate two layers into two separate containers and use the opposite of the ph range acid
or base to the aquatic layer. Then filter the aquatic layer and evaporate the organic layer.
2) recrystallization
dissolve the mixture in hot ethanol drops by drops until all the solid solve then add hot water until precipitate appears in the solution. Then wait until
the solution turns to room temperature do an ice bath for 15 mins. After that, vacuum filter the solution for 15 mins and in the end using ice water to
wash the precipitate
Observation: We decide to run recrystallization to separate two compounds in the mixture since two compounds have the same chemical properties.
The 4-bromoacetanilide solid from the stock room is brown and orange color shiny solid powder. The solid we got from the recrystallization is white fluffy solid
powder.
the crude solid of the mixture is 0.477g
after recrystallization: 0.374g
The melting point of the recrystallization production is 165.4-170.8 °C
After the recrystallization, we did another TLC testing of our production with 4-bromoacetanilide and 2-bromoacetanilide
production #1
Rf 0.636
#2
4-bromoacetanilide
2-bromoacetanilide
0.333
0.364
0.667
On the TLC testing, there are still two spots on the recrystallization production but the top one is really tiny.

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