finished report

:

main.tex

@@ -37,7 +37,7 @@
 \affil[1]{Plano East Senior High School, Plano, TX, United States}
 
 \title{Acid-Catalyzed Tandem Hydrolysis--Esterification of Acetylsalicylic Acid 
-from Commerical Asprin Tablets to Form Methyl Salicylate}
+from Commerical Aspirin Tablets to Form Methyl Salicylate}
 % Use the \date command for email address(s) of corresponding authors
 
 
@@ -94,7 +94,7 @@ has simply been esterified differently than ASA.\\
   \label{fig:methyl-salicylate}
 \end{figure}
 
-Due to the similarity between the two molecules, ASA can be reacted to synthesize methyl salicylate~\cite{Hartel2009}. 
+Due to the similarity between the two molecules, ASA can be reacted to synthesize methyl salicylate~\cite{Hartel2009,nilered2017aspirin}. 
 The purpose of this experiment was to convert acetylsalicylic acid obtained from 
 commercial aspirin tablets into methyl salicylate through acid-catalyzed esterification 
 in methanol under reflux conditions.
@@ -127,152 +127,124 @@ The heterogeneous mixture was subsequently clarified via filtration through a ce
 \end{table}
 
 
-\subsection{Outline}
+\subsection{\ce{H2SO4} Catalyzed Tandem Hydrolysis--Esterification}
 
-The document layout should follow the style of the journal concerned. Where
+The conversion of ASA to methyl salicylate proceeds via a one-pot tandem sequence (Scheme~\ref{sch:mechanism}). Concentrated \ce{H2SO4} serves as a Brønsted acid catalyst, activating the carbonyl groups toward nucleophilic attack by methanol, and as a dehydrating agent to shift the equilibrium.
-appropriate, sections and subsections should be added in the normal way.
 
-\subsection{References}
+\begin{scheme}[H]
-
-References should be given in the normal way in \LaTeX{}. If you are using
-\textsf{biblatex} (as recommended) then you can use the full range of citation
-commands it provides. If you choose to use classical Bib\TeX{}, the
-\textsf{natbib} package will be loaded and you can use it's commands.
-
-\subsection{Floats}
-
-New float types are set up in the preamble. The means graphics are included as
-follows (Scheme~\ref{sch:example}). As illustrated, the float is ``here'' if
-possible.
-\begin{scheme}
   \centering
-  Your scheme graphic would go here: PDF graphics are recommended.
+  \small
-  %\includegraphics{graphic}
+  \setchemfig{atom sep=2.0em, compound sep=5em, nodesep=2pt}
-  \caption{An example scheme}
+  
-  \label{sch:example}
+  % Wrapper to ensure vertical alignment of the three main components
+  \begin{tabular}{ccc}
+    \chemname{
+      \chemfig{*6(-=-(-O-[:-30](=[:-90]O)-[:+30]CH_3)=([:60]-[:90](=[:150]O)-[:30]OH)-=)}
+    }{\footnotesize Acetylsalicylic Acid}
+    & 
+    \parbox{2.5cm}{\centering $\xrightarrow[\Delta]{\ce{CH3OH, H2SO4}}$} 
+    & 
+    \chemname{
+      \chemfig{*6(-=-(-OH)=([:60]-[:90](=[:150]O)-[:30]O-[:+90]CH_3)-=)}
+    }{\footnotesize Methyl Salicylate}
+  \end{tabular}
+
+  \vspace{1.5em}
+  \caption{Tandem deacetylation and Fischer esterification sequence.}
+  \label{sch:mechanism}
 \end{scheme}
 
+The transformation encompasses two concurrent equilibrium-driven processes:
 
+\begin{enumerate}
+    \item \textbf{Acid-Catalyzed Solvolysis:} The acetoxy group undergoes transesterification with methanol to yield salicylic acid and methyl acetate (Eq~\ref{eq:solvolysis}).
+    \item \textbf{Fischer Esterification:} The carboxylic acid is esterified by the methanol solvent (Eq~\ref{eq:fischer}).
+\end{enumerate}
 
-The use of the different floating environments is not required, but it is
-intended to make document preparation easier for authors. In general, you
-should place your graphics where they make logical sense; the production
-process will move them if needed.
-
-\subsection{Math}
-
-If packages such as \textsf{amsmath} are required, they should be loaded in the
-preamble. However, the basic \LaTeX\ math(s) input should work correctly
-without this. Some inline material $1 + 1 = 2$ followed by some display. \[ A =
-\pi r^2 \]
-
-It is possible to label equations in the usual way (Eq.~\ref{eqn:example}).
 \begin{equation}
-  \frac{\mathrm{d}}{\mathrm{d}x} \, r^2 = 2r \label{eqn:example}
+    \ce{R-OCOCH3 + CH3OH <=>[H+] R-OH + CH3COOCH3}
+    \label{eq:solvolysis}
 \end{equation}
-This can also be used to have equations containing graphical content. To align
+
-the equation number with the middle of the graphic, rather than the bottom, a
-minipage may be used.
 \begin{equation}
-  \begin{minipage}[c]{0.80\linewidth}
+    \ce{Ar-COOH + CH3OH <=>[H+] Ar-COOCH3 + H2O}
-    \centering
+    \label{eq:fischer}
-    As illustrated here, the width of \\
-    the minipage needs to allow some  \\
-    space for the number to fit in to.
-    %\includegraphics{graphic}
-  \end{minipage}
-  \label{eqn:graphic}
 \end{equation}
 
+To drive the reaction toward the methyl salicylate product, a substantial stoichiometric excess of methanol was employed, utilizing Le Chatelier's principle to overcome the reversible nature of the esterification.
+
+\subsection{Kinetic and Thermodynamic Analysis}
+
+The transformation efficiency of the tandem hydrolysis--esterification is determined by the interplay between reaction rate and equilibrium position.
+
+\subsubsection{Thermal Activation and Collision Theory}
+The reflux duration is required to provide the activation energy ($E_{a}$) necessary for the nucleophilic attack on the sterically hindered aryl ester. According to the Arrhenius relationship, the rate constant $k$ increases exponentially with temperature:
+\begin{equation}
+    k = Ae^{-E_{a}/RT}
+\end{equation}
+Operating at the boiling point of the solvent increases the frequency of effective collisions and facilitates the formation of the required carbocation intermediates. 
+
+Furthermore, by employing a vast molar excess of methanol, the system effectively follows pseudo-first-order kinetics. Under these conditions, the concentration of the alcohol remains negligible in its variation, and the rate depends solely on the concentration of the limiting aspirin precursor:
+\begin{equation}
+    -\frac{d[\text{ASA}]}{dt} = k'[\text{ASA}] \implies [\text{ASA}]_{t} = [\text{ASA}]_{0}e^{-k't}
+\end{equation}
+
+\subsubsection{Equilibrium Shifts and Chemical Potential}
+As a reversible process, the yield is limited by the equilibrium constant ($K$). Because the esterification step is endothermic ($\Delta H^\circ > 0$), the application of heat shifts the equilibrium toward the products. This temperature dependence is quantified by the Van't Hoff equation:
+\begin{equation}
+    \frac{d \ln K}{dT} = \frac{\Delta H^\circ}{RT^{2}}
+\end{equation}
+
+The high reactant-to-substrate ratio further ensures that the reaction quotient ($Q$) remains lower than $K$ throughout the process. This maintains a negative Gibbs free energy ($\Delta G$), driving the reaction toward the formation of methyl salicylate:
+\begin{equation}
+    \Delta G = \Delta G^\circ + RT \ln Q
+\end{equation}
+The combination of thermal input and stoichiometric bias effectively overcomes the reversible nature of the Fischer esterification.
+\subsection{Work-up and Purification}
+
+Following reflux, the reaction was quenched in ice-cold distilled water. Methyl salicylate ($\rho \approx 1.17$ g/mL) was isolated as the organic phase via liquid--liquid extraction. Residual acidic species (\ce{H2SO4}, \ce{CH3COOH}) were neutralized using saturated \ce{NaHCO3}:
+
+\begin{equation}
+    \ce{H2SO4(aq) + 2NaHCO3(aq) -> Na2SO4(aq) + 2CO2(g) + 2H2O(l)}
+\end{equation}
+
+The organic extract was dried over anhydrous \ce{MgSO4} and filtered to yield the pure essential oil.
+
 \section{Experimental}
 
-The usual experimental details should appear here. This could include a table,
+\subsection{Materials and Reagents}
-which can be referenced as Table~\ref{tbl:example}. Notice that the caption is
+The starting material consisted of 50 Bayer Extra Strength aspirin tablets (500~mg ASA per tablet). The reaction used ACS-grade methanol and 96\% \ce{H2SO4}. A saturated solution of commercial iodized salt was used for the salting-out step.
-positioned at the top of the table.
-\begin{table}
-  \caption{An example table}
-  \label{tbl:example}
-  \centering
-  \begin{tabular}{ll}
-    \hline
-    Header one  & Header two  \\
-    \hline
-    Entry one   & Entry two   \\
-    Entry three & Entry four  \\
-    Entry five  & Entry five  \\
-    Entry seven & Entry eight \\
-    \hline
-  \end{tabular}
-\end{table}
 
-Adding notes to tables can be complicated. Perhaps the easiest method is to
+\subsection{Extraction and Filtration}
-generate these using the basic \texttt{\textbackslash textsuperscript} and
+The 50 tablets had a total initial mass of 30.148~g. These were crushed using a mortar and pestle into a fine powder. After grinding, 28.114~g of the powder was recovered, meaning some material was lost in the mortar. Based on the ratio of the original 25.000~g of ASA in the 30.148~g bulk, the actual amount of ASA moved into the beaker was 23.313~g (0.129~mol).
-\texttt{\textbackslash emph} macros, as illustrated (Table~\ref{tbl:notes}).
-\begin{table}
-  \caption{A table with notes}
-  \label{tbl:notes}
-  \centering
-  \begin{tabular}{ll}
-    \hline
-    Header one                            & Header two \\
-    \hline
-    Entry one\textsuperscript{\emph{a}}   & Entry two  \\
-    Entry three\textsuperscript{\emph{b}} & Entry four \\
-    \hline
-  \end{tabular}
 
-  \textsuperscript{\emph{a}} Some text;
+This powder was stirred in 190~mL of methanol for an hour. The mixture was then poured through a coffee filter to strain out the starch and cellulose binders. The resulting liquid had a faint pink tint, likely from the dyes used in the tablet coating.
-  \textsuperscript{\emph{b}} Some more text.
-\end{table}
 
-The example file also loads the optional \textsf{chemformula} and
+\subsection{Tandem Reaction and Reflux}
-\textsf{mhchem} packages, so that formulas are easy to input:
+The filtered liquid was poured into a 250~mL round-bottom flask. When the 5~mL of 96\% \ce{H2SO4} was added dropwise, the flask became hot to the touch and the liquid boiled locally where the acid hit. The flask was set up with a water-cooled condenser and boiled at a steady reflux for 60~min. During this time, the liquid lost its clarity and became slightly murky.
-\texttt{\textbackslash ce\{H2SO4\}} gives \ce{H2SO4}. The two have similar
-syntax but authors may prefer one or the other.
 
-The use of new commands should be limited to simple things which will not
+\subsection{Isolation and Salting-Out}
-interfere with the production process. For example, \texttt{\textbackslash
+After boiling, the liquid was evaporated down to about 100~mL and then poured into 100~mL of ice-cold water. To help the oil separate from the water, 10~mL of saturated salt water was added. Because the total volume was too high for a single small container, the mixture was split into two 125~mL separatory funnels. In both funnels, the wintergreen oil sank to the bottom as a dense layer. These two layers were drained and combined.
-mycommand} has been defined in this example, to give italic, mono-spaced text:
-\mycommand{some text}.
 
-\section*{Acknowledgements}
+\subsection{Purification and Neutralization}
+The crude oil was washed twice with 50~mL of saturated \ce{NaHCO3} and seperated throguh gravity seperation. Both times, the mixture fizzed a lot as the acid was neutralized, so the funnel had to be vented constantly while shaking. This process removed the leftover sulfuric acid and the acetic acid byproduct, and the fizzy gas was the \ce{CO2} resulting from the neutralization reaction.
 
-Please use ``The authors thank \ldots'' rather than ``The authors would like to
+\subsection{Theoretical Yield Analysis}
-thank \ldots''.
+The final oil was dried with anhydrous \ce{MgSO4} until it looked clear and then filtered through a cotton plug. Based on the starting amount of 23.313~g of ASA, the theoretical yield of methyl salicylate is:
 
-\section*{Supporting information}
+\begin{equation}
+    \text{Mass}_{\text{theoretical}} = 0.129\text{ mol} \times 152.15\text{ g/mol} = 19.627\text{ g}
+\end{equation}
+
+The final product was a clear oil with a very strong wintergreen scent. While the final yield was not recorded, the mass of final product was 
+much lower than 19.627 g, and the researchers estimate the percent yield to be near 10\%. This low yield is likely attrributed to the 
+equillibrium nature of the reaction. Additionally, substantial oil was lost in seperation to prevent accidental 
+passage of the aqueous layer.
 
-A listing of the contents of each file supplied as Supporting Information
-should be included. For instructions on what should be included in the
-Supporting Information as well as how to prepare this material for
-publications, refer to the journal's Instructions for Authors.
 
-The following files are available free of charge.
-\begin{itemize}
-  \item Filename-1: brief description
-  \item Filename-2: brief description
-\end{itemize}
 
 \printbibliography
 
-\newpage
 
-\rule{0.05in}{1.75in}%
-\begin{minipage}[b][1.75in]{3.25in}
-  \sffamily
-  \frenchspacing
-
-  Some journals require a graphical entry for the Table of Contents. This
-  should be laid out ``print ready'' so that the sizing of the text is correct.
-
-  The space available depends on the journal: J. Am. Chem. Soc. allows 3.25 in
-  by 1.75 in and requires sanserif text. Some journals want different sizes:
-  you can easily adjust here.
-  
-  The two rules either side of the content are there to help judge the height
-  of your material: they may be deleted once not required.
-  
-\end{minipage}%
-\rule{0.05in}{1.75in}
 
 \end{document}

references.bib

@@ -54,4 +54,15 @@
   year = {2009},
   month = Apr,
   pages = {475}
+}
+
+@online{nilered2017aspirin,
+  author       = {NileRed},
+  title        = {Turning aspirin pills into mint flavor},
+  year         = {2017},
+  month        = jul,
+  day          = {17},
+  organization = {YouTube},
+  url          = {https://www.youtube.com/watch?v=3NN9IUvrKi4},
+  note         = {YouTube video, 10.7M subscribers, 2,057,102 views, accessed 2026-05-12}
 }