CHM 2123 — Laboratory Report
Fall 2022
The reductive amination of vanillin with p-toluidine
Student(s) Name(s) Asha Doughty
and Number(s) : 300226452
This report is: Individual
Date: November 10, 2022
Teaching Assistant: Samuel Delisle
Weekly Lab Period Thursday
COMMENTS
• Your report is submitted electronically via Brightspace into the dedicated folder.
• This report can be completed individually or in pairs, with your assigned lab partner, to each student’s
preference. If done in pairs, each student must submit an identical copy of the pre-lab. Make sure to include
both your names and student numbers above. Both students will receive the same marks and comments.
• This lab report is due on the week of November 7th, by the beginning of your respective lab section. Do
not trust Brightspace’s due date: since every student share the same Brightspace page, the due date found
online is for the last section of the week.
• Your results and report covers the three reactions done for this experiment. Type all the answers using Arial
font, size 12 pt, directly in the cells provided. The cells are representative of the length of the expected
answer, and their sizes have been locked to discourage superfluously long answers. Anything exceeding
this expected length may be ignored by the TA.
• Molecular figures must be drawn using ChemDraw.
• Late penalty is 20%/day, starting the moment the report is due and going up every 24h.
Point distribution
Introduction and Experimental Section /8
Results and Observations /12
Calculations /1
Discussion /39
Post-Lab Question /17
Conclusion /5
Appendix /2
TOTAL /84
,Introduction and Experimental Section
Explain briefly, and in your words, the objectives of this experiment, the key theory behind the
reaction of interest, and a short description of the procedure and techniques employed to achieve
your goal. This description should cover the chemical transformations that are being done, as well
as (if relevant) the purpose of the various reagents used. In addition, explain the relevance of the
key steps toward your final goal. (8 pts)
The goal of this experiment was to synthesize an amide by reducing an amine. In addition,
verifying the purity and identity of the product and intermediates.
To achieve this goal, vanillin and p-Toluidine were mixed in a beaker. The resulting product was
analyzed by TLC and melting point analysis to verify that it was the expected imine, and that the
reaction was complete. After, the imine was reduced by adding ethanol and NaBH4. The
resulting product was analyzed by TLC to verify that it was the expected secondary amine
intermediate, and that the reaction was complete. Next, an acetylation reaction occurred when
acetic acid and acetic anhydride was added. The reaction proceeded under mild heat. The
resulting product was analyzed by TLC to verify that it was the expected final amide product, and
that the reaction was complete. Afterwards, the solution was stirred in an ice bath while a
separatory funnel dispensed drops of water to precipitate the product. The solid product was
filtered using a vacuum filtration set up and dried using a water aspirator set up. The final solid
was weighed and was analyzed to confirm it was the amide through TLC and melting point
analysis.
In this experiment, two reactions were performed. First, a reductive amination. A reductive
amination consists of two steps that can be completed sequentially without any intermediary
tasks (“one pot”). In the first step, a nucleophilic primary amine (p-toluidine) attacks an
electrophilic carbon (vanillin) forming an intermediary imine. The imine acts as an electrophile
instead of a nucleophile and is thus reduced with a reducing agent (NaBH4) to form a secondary
amine. Since secondary amines are more nucleophilic than primary amines, reductive amination
reactions are required to prevent any unwanted reactions. The second reaction is an acetylation
reaction. The secondary amine is turned into a very stable amide when acetic acid and acetic
anhydride is added.
, Results and Observations
Using ChemDraw, replicate the TLC results obtained throughout the experiment, which should
include:
• Your results for the optimization step, including your results for vanillin and toluidine in the
various solvents tried, ranking your plates in increasing order of eluent strength (regardless
of the order they were done in).
• The TLC results for monitoring the various reactions performed during the experiment.
• TLC characterization of the isolated amide product.
Make sure to properly label your drawings. On the drawing (or alternatively in table form), list all
of the measured distances and Rf for all spots observed, along with their respective colors, if any.
(5 pts)
Fall 2022
The reductive amination of vanillin with p-toluidine
Student(s) Name(s) Asha Doughty
and Number(s) : 300226452
This report is: Individual
Date: November 10, 2022
Teaching Assistant: Samuel Delisle
Weekly Lab Period Thursday
COMMENTS
• Your report is submitted electronically via Brightspace into the dedicated folder.
• This report can be completed individually or in pairs, with your assigned lab partner, to each student’s
preference. If done in pairs, each student must submit an identical copy of the pre-lab. Make sure to include
both your names and student numbers above. Both students will receive the same marks and comments.
• This lab report is due on the week of November 7th, by the beginning of your respective lab section. Do
not trust Brightspace’s due date: since every student share the same Brightspace page, the due date found
online is for the last section of the week.
• Your results and report covers the three reactions done for this experiment. Type all the answers using Arial
font, size 12 pt, directly in the cells provided. The cells are representative of the length of the expected
answer, and their sizes have been locked to discourage superfluously long answers. Anything exceeding
this expected length may be ignored by the TA.
• Molecular figures must be drawn using ChemDraw.
• Late penalty is 20%/day, starting the moment the report is due and going up every 24h.
Point distribution
Introduction and Experimental Section /8
Results and Observations /12
Calculations /1
Discussion /39
Post-Lab Question /17
Conclusion /5
Appendix /2
TOTAL /84
,Introduction and Experimental Section
Explain briefly, and in your words, the objectives of this experiment, the key theory behind the
reaction of interest, and a short description of the procedure and techniques employed to achieve
your goal. This description should cover the chemical transformations that are being done, as well
as (if relevant) the purpose of the various reagents used. In addition, explain the relevance of the
key steps toward your final goal. (8 pts)
The goal of this experiment was to synthesize an amide by reducing an amine. In addition,
verifying the purity and identity of the product and intermediates.
To achieve this goal, vanillin and p-Toluidine were mixed in a beaker. The resulting product was
analyzed by TLC and melting point analysis to verify that it was the expected imine, and that the
reaction was complete. After, the imine was reduced by adding ethanol and NaBH4. The
resulting product was analyzed by TLC to verify that it was the expected secondary amine
intermediate, and that the reaction was complete. Next, an acetylation reaction occurred when
acetic acid and acetic anhydride was added. The reaction proceeded under mild heat. The
resulting product was analyzed by TLC to verify that it was the expected final amide product, and
that the reaction was complete. Afterwards, the solution was stirred in an ice bath while a
separatory funnel dispensed drops of water to precipitate the product. The solid product was
filtered using a vacuum filtration set up and dried using a water aspirator set up. The final solid
was weighed and was analyzed to confirm it was the amide through TLC and melting point
analysis.
In this experiment, two reactions were performed. First, a reductive amination. A reductive
amination consists of two steps that can be completed sequentially without any intermediary
tasks (“one pot”). In the first step, a nucleophilic primary amine (p-toluidine) attacks an
electrophilic carbon (vanillin) forming an intermediary imine. The imine acts as an electrophile
instead of a nucleophile and is thus reduced with a reducing agent (NaBH4) to form a secondary
amine. Since secondary amines are more nucleophilic than primary amines, reductive amination
reactions are required to prevent any unwanted reactions. The second reaction is an acetylation
reaction. The secondary amine is turned into a very stable amide when acetic acid and acetic
anhydride is added.
, Results and Observations
Using ChemDraw, replicate the TLC results obtained throughout the experiment, which should
include:
• Your results for the optimization step, including your results for vanillin and toluidine in the
various solvents tried, ranking your plates in increasing order of eluent strength (regardless
of the order they were done in).
• The TLC results for monitoring the various reactions performed during the experiment.
• TLC characterization of the isolated amide product.
Make sure to properly label your drawings. On the drawing (or alternatively in table form), list all
of the measured distances and Rf for all spots observed, along with their respective colors, if any.
(5 pts)
