From: Sam W Date: Sat, 2 Dec 2017 20:09:22 +0000 (+0000) Subject: Initial commit with experiment 3A, 7A and 10A lab reports and bibliographies. X-Git-Url: https://git.dalvak.com/public/?a=commitdiff_plain;h=91d43f7faa98de25411f3a3bd41523a1fdb36186;p=chemistry%2Funiversity-chemistry-lab-reports.git Initial commit with experiment 3A, 7A and 10A lab reports and bibliographies. --- 91d43f7faa98de25411f3a3bd41523a1fdb36186 diff --git a/.gitignore b/.gitignore new file mode 100644 index 0000000..4811c59 --- /dev/null +++ b/.gitignore @@ -0,0 +1,23 @@ +*.aux +*.glo +*.idx +*.log +*.toc +*.ist +*.acn +*.acr +*.alg +*.bbl +*.blg +*.dvi +*.glg +*.gls +*.ilg +*.ind +*.lof +*.lot +*.maf +*.mtc +*.mtc1 +*.out +*.synctex.gz diff --git a/10a/10a.bcf b/10a/10a.bcf new file mode 100644 index 0000000..1402288 --- /dev/null +++ b/10a/10a.bcf @@ -0,0 +1,1961 @@ + + + + + + output_encoding + ascii + + + input_encoding + ascii + + + debug + 0 + + + mincrossrefs + 2 + + + minxrefs + 2 + + + sortcase + 1 + + + sortupper + 1 + + + + + + + alphaothers + + + + + labelalpha + 0 + + + labelnamespec + shortauthor + author + shorteditor + editor + 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verbose.bbx + authortitle.bbx + standard.bbx + verbose.cbx + biblatex.cfg + british.lbx + english.lbx + + + + biber + + biber + 10a + + + 10a.bcf + + + 10a.bbl + + + 10a.bbl + + + 10a.bcf + + + ../bibliographies/reference.bib + + + diff --git a/10a/10a.tex b/10a/10a.tex new file mode 100644 index 0000000..6c9aa5a --- /dev/null +++ b/10a/10a.tex @@ -0,0 +1,228 @@ +%Document Setup. +\documentclass{article} +\usepackage{graphicx} %Allows import of images. +%\usepackage{float} +\usepackage{floatrow} %Align tables and figures side-by-side. +\usepackage[extreme,mathspacing=normal,leading=normal]{savetrees} %Reduce whitespace. +\usepackage{siunitx} %SI Units formatting. +%\usepackage{vhistory} %Revision History. +\usepackage[version=4]{mhchem} %Chemical Equations. +\usepackage{amsmath} %Mathematical alignments. +\usepackage{amssymb} %Mathematical symbols e.g. therefore. +\usepackage[parfill]{parskip} %Blank lines between paragraphs. +\usepackage[autostyle]{csquotes} +\usepackage{array} %Table centering. +\usepackage[british]{babel} %British localisation. +\usepackage[backend=biber,style=verbose]{biblatex} %Bibliography. + +\numberwithin{equation}{subsection} %Number equations based on their subsection. +\bibliography{../bibliographies/reference} %Use Bibliography of reference books. +\floatsetup[table]{style=plaintop} %Put captions on top of tables. +\floatsetup[figure]{style=plain} %Ensure figure captions are below figures. + +%Document Headings. +\begin{document} +\title{Preparation of Aspirin (10A/PA)} +\author{Sam White} +\date{28/11/2017} +%\date{\vhCurrentDate\\\vhCurrentVersion} +\maketitle + +\section{Reaction Mechanism and Overall Equation} +\begin{figure}[H] + \centering + \includegraphics[width=0.85\textwidth]{Mechanism.png} + \caption{Mechanism for the reaction where ROH is salicylic acid.\label{fig:mechanism}} +\end{figure} +\begin{figure}[H] + \centering + \includegraphics[width=0.55\textwidth]{Equation.png} + \caption{Equation for the reaction.\label{fig:equation}} +\end{figure} + +\section{Summary of Method} +Salicylic acid (\SI{3.50}{\gram}), glacial acetic acid (\SI{5}{\centi\metre\cubed}) and acetic anhydride (\SI{3}{\centi\metre\cubed}) were boiled under reflux for 10 minutes. The product was precipitated by pouring into ice-cold water (\SI{75}{\centi\metre\cubed}) and then recrystallised in a water and glacial acetic acid mixture (1:1 by volume) using ice to cool the mixture. The crude product, recrystallised product, salicylic acid and a sample of pure aspirin (each in \SI{0.5}{\centi\metre\cubed} dichloromethane) were then analysed using thin-layer chromatography (TLC) with light petroleum ether and ethyl acetate (70:30 by volume) as the TLC solvent. The melting point of the purified product was then determined. + +\section{Results and Analysis} + +{\centering Mass of purified product: \SI{3.99}{\gram} + +} + +\subsection{Thin-Layer Chromatography (TLC) Results} \label{tlc-results} +\begin{table}[H] + \centering + \begin{tabular}{|c|c|c|} + \hline + Substance & $R_{f}$ Value of First Spot & $R_{f}$ Value of Second Spot \\ + \hline + Salicylic acid & 0.64 & N/A \\ + \hline + Pure aspirin & 0.32 (Diffuse) & N/A \\ + \hline + Crude product & 0.42 & 0.58 \\ + \hline + Purified product & 0.43 & N/A \\ + \hline + \end{tabular} +\end{table} +The crude product gave two distinct spots on the TLC plate indicating the presence of two substances in the sample. The $R_{f}$ value for the first spot (at 0.42) is different to that for the aspirin, however the aspirin produced a diffuse mark on the plate (possibly since too much solution was added to the plate) with the $R_{f}$ values for the bottom and top of the mark being 0.18 and 0.45 respectively. The $R_{f}$ value for the first spot from the crude product is within this range, hence suggesting that the crude product contains aspirin. The $R_{f}$ value of 0.58 for the second spot of the crude product is close to the $R_{f}$ value of the salicylic acid which suggests the presence of salicylic acid as an impurity in the product. This indicates that the reaction did not proceed to completion since the salicylic acid was the limiting reagent (see the percentage yield calculation in section~\ref{yield-calculation}). This is expected since the reaction is reversible (see figure~\ref{fig:mechanism}), hence an equilibrium between the reactants and products will be established. + +The TLC result for the purified product only shows a single spot at almost the same position as that for the spot assigned to aspirin in the crude product. This suggests that the recrystallisation was effective at removing the salicylic acid impurity since the spot due to this impurity is no longer present. + +\subsection{Melting Point Determination} \label{melting-point} +\begin{table}[H] + \caption{Melting Point Determination Results.} + \centering + \begin{tabular}{|c|c|c|} + \hline + Run & Melting Started / \si{\celsius} & Melting Finished / \si{\celsius} \\ + \hline + 1 & 95.1 & 101.9 \\ + \hline + 2 & 88.7 & 112.0 \\ + \hline + 3 & 91.1 & 100.4 \\ + \hline + \end{tabular} +\end{table} +The expected melting point for aspirin is \SI{136}{\celsius}.\footcite[Physical Constants of Organic Compounds, 3-8]{crc-handbook} The melting temperature results show a wide temperature range of over \SI{10}{\celsius} for the melting of the product and the temperature at which the product melted is much lower than the expected value. This is likely to have occurred since the product was not completely dry (the product consisted of clumps and upon grinding with a pestle and mortar some of the product formed a thin paste instead of forming a fine powder). + +To reduce the amount of solvent contaminating the product it could have been left in the B\"{u}chner funnel for a longer period of time after the final filtration, however it is unlikely that this would result in a fully dried product since the solvent used was not particularly volatile (the boiling temperature of water is \SI{100}{\celsius} and that of acetic acid is \SI{117.9}{\celsius}\footcite[Physical Constants of Organic Compounds, 3-4]{crc-handbook}). A more effective way to dry the product would have been to leave it in a vacuum desiccator overnight, since then the ambient pressure would be reduced below the vapour pressure of the solvent, hence causing it to evaporate much faster and leave a drier product. + +\subsection{Yield Calculation} \label{yield-calculation} +The density of acetic anhydride is \SI{1.082}{\gram\per\centi\metre\cubed}.\footcite[Physical Constants of Organic Compounds, 3-4]{crc-handbook} +\begin{displaymath} + \begin{aligned} + \text{Moles of salicylic acid at start of reaction} &= \frac{\SI{3.50}{\gram}}{(7(12.011) + 6(1.008) + 3(15.999)) \text{ \si{\gram\per\mole}}} \\ + &= \frac{\SI{3.50}{\gram}}{\SI{138.122}{\gram\per\mole}} = \SI{0.0253}{\mole} \\ + \text{Moles of acetic anhydride at start of reaction} &= \frac{\SI{3.00}{\centi\metre\cubed} \times \SI{1.082}{\gram\per\centi\metre\cubed}}{(4(12.011) + 6(1.008) + 3(15.999))\text{ \si{\gram\per\mole}}} \\ + &= \frac{\SI{3.246}{\gram}}{\SI{102.089}{\gram\per\mole}} = \SI{0.0318}{\mole} + \end{aligned} +\end{displaymath} + +From the equation (see figure~\ref{fig:equation}) there is a 1:1 molar ratio between salicylic acid and acetic anhydride, hence the acetic anhydride is in excess. The equation also shows a 1:1 molar ratio between the salicylic acid and aspirin, hence the theoretical amount of aspirin produced is \SI{0.0253}{\mole}. + +\begin{displaymath} + \begin{aligned} + \therefore \text{Theoretical yield of aspirin} &= \SI{0.0253}{\mole} \times (9(12.011) + 8(1.008) + 4(15.999)) \text{ \si{\gram\per\mole}} \\ + &= \SI{0.0253}{\mole} \times \SI{180.159}{\gram\per\mole} = \SI{4.57}{\gram} \\ + \therefore \text{Percentage yield} &= \frac{\SI{3.99}{\gram}}{\SI{4.57}{\gram}} \times \SI{100}{\percent} = \SI{87.4}{\percent} + \end{aligned} +\end{displaymath} + +This is very high: this is because the aspirin was not fully dry before the mass was determined (see section~\ref{melting-point}). This yield value is much higher than expected since the reaction is reversible and hence will not proceed to completion (as shown in section~\ref{tlc-results} with the TLC results of the crude product). + +In addition there were significant transfer losses at all transfers since the product was difficult to completely remove the sides of the vessels and while washing with ice-cold water aided in the transfer of product this would have also reduced the yield since some of the product would have dissolved in the water. + +\subsection{Spectra} +\begin{table}[H] +\begin{floatrow} + \CenterFloatBoxes + \ttabbox + {\caption{IR Spectrum of Salicylic Acid.}} + {\begin{tabular}{|c|c|c|} + \hline + Wavenumber / \si{\per\centi\metre} & Strength & Assignment \\ + \hline + 1609.7 & Moderate & \ce{C=C} Absorption. \\ + \hline + 1651.5 & Moderate & \ce{C=O} Absorption. \\ + \hline + 2850.8 & Weak and Broad & \ce{O-H} Absorption in hydroxyl group. \\ + \hline + \end{tabular} + } + \killfloatstyle + \ffigbox + {\includegraphics[height=2cm]{Salicylic-acid-NMR.png}\label{fig:salicylic-acid-nmr}} + {\caption{Salicylic acid.}} +\end{floatrow} +\end{table} + +\begin{table}[H] + \caption{$^1$H NMR Spectrum of Salicylic Acid in DMSO.} + \centering + \begin{tabular}{|c|>{\centering}m{3.3cm}|>{\centering}m{2.2cm}|m{7.9cm}|} + \hline + Chemical Shift / ppm & $J$-Coupling & Integral Area & Summary \\ + \hline + 9.6 & Broad Singlet & Not Integrated & Proton in (6) (carboxyl group). \\ + \hline + 7.6 & Doublet of Doublets & 4.00 & Proton in (5), coupling with (4) and (3). \\ \cline{1-2} \cline{4-4} + 7.2 & Doublet of Doublets & & Proton in (2), coupling with (3) and (4). \\ \cline{1-2} \cline{4-4} + 6.6 & Triplet of Doublets (Considerable Roofing) & (Integrated together) & One proton in (3) and one in (4), coupling with (2) and (5) (and with each other). \\ + \hline + 2.4 & Singlet & 0.17 & Characteristic of \ce{DMSO} (solvent). \\ + \hline + \end{tabular} +\end{table} +\begin{table}[H] + \caption{IR Spectrum of Acetic Anhydride.} + \centering + \begin{tabular}{|c|c|c|} + \hline + Wavenumber / \si{\per\centi\metre} & Strength & Assignment \\ + \hline + 1751.0 & Strong & \ce{C=O} Absorption. \\ + \hline + 1821.9 & Strong & \ce{C=O} Absorption. \\ + \hline + \end{tabular} +\end{table} +\begin{table}[H] + \caption{$^1$H NMR Spectrum of Acetic Anhydride.} + \centering + \begin{tabular}{|c|c|c|c|} + \hline + Chemical Shift / ppm & $J$-Coupling & Integral Area & Summary \\ + \hline + 2.3 & Singlet & 1.00 & Six protons in equivalent environment (from the two methyl groups). \\ + \hline + \end{tabular} +\end{table} + +\begin{table}[H] +\begin{floatrow} + \CenterFloatBoxes + \ttabbox + {\caption{IR Spectrum of Product.}} + {\begin{tabular}{|c|c|c|} + \hline + Wavenumber / \si{\per\centi\metre} & Strength & Assignment \\ + \hline + 1602.5 & Moderate & \ce{C=C} Absorption. \\ + \hline + 1681.7 & Strong & \ce{C=O} Absorption. \\ + \hline + 1750.4 & Moderate & \ce{C=O} Absorption. \\ + \hline + 2835.7 & Weak and Broad & \ce{O-H} in hydroxyl group. \\ + \hline + \end{tabular} + } + \killfloatstyle + \ffigbox + {\includegraphics[height=2cm]{Aspirin-NMR.png}\label{fig:aspirin-nmr}} + {\caption{Aspirin.}} +\end{floatrow} +\end{table} + +\begin{table}[H] + \caption{$^1$H NMR Spectrum of Product.} + \centering + \begin{tabular}{|c|c|c|p{7.9cm}|} + \hline + Chemical Shift / ppm & $J$-Coupling & Integral Area & Summary \\ + \hline + 8.4-6.8 & Complex Multiplet & 16.21 & Protons (2), (3), (4) and (5) from aspirin and salicylic acid impurity. \\ + \hline + 2.4 & Singlet & 7.40 & Six protons from acetic anhydride impurity. \\ + \hline + 2.2 & Singlet & 3.00 & Three protons in (1) from aspirin. \\ + \hline + \end{tabular} +\end{table} + +The product used for the $^1$H NMR spectra was not pure since the spectrum contains a singlet peak from the two methyl groups in acetic anhydride and the relative area for the aromatic peaks is greater than four with a poorly defined splitting patten, hence indicating the presence of salicylic acid. Some aspirin can be seen to have been produced by the presence of the additional peak at 2.2 ppm due to the three protons in (1). The composition of the product can be determined by comparing the areas of the peaks sue to each substance and is 1.00:1.23:3.05 (aspirin:acetic anhydride:salicylic acid). This indicates that the purification steps were not very successful since the sample mostly consisted of impurities. The IR spectrum shows that aspirin was produced since the number of peaks due to carbonyl bonds increased from the one in salicylic acid to two in the product: is expected for an acylation. +\end{document} diff --git a/10a/Aspirin-NMR.png b/10a/Aspirin-NMR.png new file mode 100755 index 0000000..b9cf6f8 Binary files /dev/null and b/10a/Aspirin-NMR.png differ diff --git a/10a/Equation.png b/10a/Equation.png new file mode 100755 index 0000000..c18da07 Binary files /dev/null and b/10a/Equation.png differ diff --git a/10a/Mechanism.png b/10a/Mechanism.png new file mode 100755 index 0000000..5534a79 Binary files /dev/null and b/10a/Mechanism.png differ diff --git a/10a/Salicylic-acid-NMR.png b/10a/Salicylic-acid-NMR.png new file mode 100755 index 0000000..15376e2 Binary files /dev/null and b/10a/Salicylic-acid-NMR.png differ diff --git a/3a/3a.bcf b/3a/3a.bcf new file mode 100644 index 0000000..c3af979 --- /dev/null +++ b/3a/3a.bcf @@ -0,0 +1,2147 @@ + + + + + + output_encoding + ascii + + 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../bibliography/coretextbooks.bib + + + diff --git a/3a/3a.tex b/3a/3a.tex new file mode 100644 index 0000000..1ad6fda --- /dev/null +++ b/3a/3a.tex @@ -0,0 +1,160 @@ +%Document Setup. +\documentclass{article} +\usepackage{graphicx} %Allows import of images. +\usepackage{float} +\usepackage[extreme,mathspacing=normal,leading=normal]{savetrees} %Reduce whitespace. +\usepackage{siunitx} %SI Units formatting. +%\usepackage{vhistory} %Revision History. +\usepackage[version=4]{mhchem} %Chemical Equations. +\usepackage{amsmath} %Mathematical alignments. +\usepackage{amssymb} %Mathematical symbols e.g. therefore. +\usepackage[parfill]{parskip} %Blank lines between paragraphs. +\usepackage[autostyle]{csquotes} +\usepackage[british]{babel} %British localisation. +\usepackage[backend=biber]{biblatex} %Bibliography. + +\numberwithin{equation}{subsection} %Number equations based on their subsection. +\bibliography{../bibliography/coretextbooks} %Use Bibliography of Core textbooks. + +%Document Headings. +\begin{document} +\title{Determination of the $M_{r}$ of an Unknown Solid Acid using Titration (3A/ABT)} +\author{Sam White} +\date{31/10/2017} +%\date{\vhCurrentDate\\\vhCurrentVersion} +\maketitle + +\section{Aim} +To determine the $M_r$ of an unknown solid acid ($A$) using a titrimetric method of analysis. + +\section{Results and Analysis} +\begin{displaymath} + \begin{aligned} + \text{Batch of \ce{HCl} used}&: B \\ + \text{Concentration of \ce{HCl}}&: \SI{0.1029}{\mole\per\deci\metre\cubed} \\ + \text{Batch of \ce{NaOH} Used}&: B + \end{aligned} +\end{displaymath} + +\subsection{Titration between \ce{NaOH} and \ce{HCl}} +\begin{equation} \label{eq:naoh-hcl} + \ce{HCl(aq) + NaOH(aq) -> NaCl(aq) + H2O(l)} +\end{equation} + +Phenolphthalein was used as the indicator (colour change from pink to colourless at the end point). + +\begin{table}[h] + \caption{Results from titrating \SI{25.00}{\centi\metre\cubed} of \ce{NaOH} with \ce{HCl}.} + \centering + \begin{tabular}{|c|c|c|c|} + \hline + {Run} & {Start Volume / \si{\centi\metre\cubed}} & {End Volume / \si{\centi\metre\cubed}} & {Titre / \si{\centi\metre\cubed}} \\ + \hline + 1 & 6.60 & 30.95 & 24.35 \\ + \hline + 2 & 2.00 & 25.85 & 23.85 \\ + \hline + 3 & 4.20 & 28.30 & 24.10 \\ + \hline + 4 & 4.45 & 28.55 & 24.10 \\ + \hline + \end{tabular} +\end{table} + +\begin{displaymath} + \text{Average titre} = \frac{\SI{24.10}{\centi\metre\cubed} + \SI{24.10}{\centi\metre\cubed}}{2} = \SI{24.10}{\centi\metre\cubed} +\end{displaymath} + +\begin{displaymath} + \begin{aligned} + \text{Moles of \ce{HCl} in titre} &= \SI{24.10}{\centi\metre\cubed} \times (\frac{\SI{1}{\deci\metre}}{\SI{10}{\centi\metre}})^3 \times \SI{0.1029}{\mole\per\deci\metre\cubed} \\ + &= \SI{24.10e-3}{\deci\metre\cubed} \times \SI{0.1029}{\mole\per\deci\metre\cubed} \\ + &= \SI{2.480e-3}{\mole} + \end{aligned} +\end{displaymath} + +From equation~\ref{eq:naoh-hcl} there is a 1:1 molar ratio between \ce{HCl} and \ce{NaOH}. + +\begin{displaymath} + \begin{aligned} + \therefore \text{Moles of \ce{NaOH} in \SI{25.00}{\centi\metre\cubed}} &= \SI{2.480e-3}{\mole} \\ + \text{Concentration of \ce{NaOH}} &= \frac{\SI{2.480e-3}{\mole}}{\SI{25.00}{\centi\metre\cubed} \times (\frac{\SI{1}{\deci\metre}}{\SI{10}{\centi\metre}})^3} \\ + &= \frac{\SI{2.480e-3}{\mole}}{\SI{25.00e-3}{\deci\metre\cubed}} \\ + &= \SI{0.09920}{\mole\per\deci\metre\cubed} + \end{aligned} +\end{displaymath} + + +\subsection{Titration between \ce{NaOH} and Unknown Acid $A$} +For \ce{HA} being the unknown acid $A$ and assuming \ce{HA} is monobasic: +\begin{equation} \label{eq:naoh-ha} + \ce{HA(aq) + NaOH(aq) -> NaA(aq) + H2O(l)} +\end{equation} + +Phenolphthalein was used as the indicator (colour change from pink to colourless at the end point). + +A mass of \SI{1.8525}{\gram} of \ce{HA} was dissolved with distilled water in a \SI{200.00}{\centi\metre\cubed} volumetric flask. + +\begin{table}[h] + \caption{Results from titrating \SI{20.00}{\centi\metre\cubed} of \ce{NaOH} with \ce{HA}.} + \centering + \begin{tabular}{|c|c|c|c|} + \hline + {Run} & {Start Volume / \si{\centi\metre\cubed}} & {End Volume / \si{\centi\metre\cubed}} & {Titre / \si{\centi\metre\cubed}} \\ + \hline + 1 & 4.00 & 24.90 & 20.90 \\ + \hline + 2 & 4.00 & 24.10 & 20.10 \\ + \hline + 3 & 4.05 & 24.20 & 20.15 \\ + \hline + \end{tabular} +\end{table} + +\begin{displaymath} + \text{Average titre} = \frac{\SI{20.10}{\centi\metre\cubed} + \SI{20.15}{\centi\metre\cubed}}{2} = \SI{20.13}{\centi\metre\cubed} +\end{displaymath} + +\begin{displaymath} + \begin{aligned} + \text{Moles of \ce{NaOH} in \SI{20.00}{\centi\metre\cubed} aliquot} &= \SI{20.00}{\centi\metre\cubed} \times (\frac{\SI{1}{\deci\metre}}{\SI{10}{\centi\metre}})^3 \times \SI{0.09920}{\mole\per\deci\metre\cubed} \\ + &= \SI{20.00e-3}{\deci\metre\cubed} \times \SI{0.09920}{\mole\per\deci\metre\cubed} \\ + &= \SI{1.984e-3}{\mole} + \end{aligned} +\end{displaymath} + +From equation \ref{eq:naoh-ha} there is a 1:1 molar ratio between \ce{NaOH} and \ce{HA}. + +\begin{displaymath} + \begin{aligned} + \therefore \text{Moles of \ce{HA} in \SI{20.13}{\centi\metre\cubed}} &= \SI{1.984e-3}{\mole} \\ + \text{Concentration of \ce{HA}} &= \frac{\SI{1.984e-3}{\mole}}{\SI{20.13}{\centi\metre\cubed} \times (\frac{\SI{1}{\deci\metre}}{\SI{10}{\centi\metre}})^3} \\ + &= \frac{\SI{1.984e-3}{\mole}}{\SI{20.13e-3}{\deci\metre\cubed}} \\ + &= \SI{0.09855}{\mole\per\deci\metre\cubed} + \end{aligned} +\end{displaymath} + +Hence for the whole \SI{200.00}{\centi\metre\cubed} volumetric flask: +\begin{displaymath} + \begin{aligned} + \text{Moles of \ce{HA}} &= \SI{0.09855}{\mole\per\deci\metre\cubed} \times \SI{200.00}{\centi\metre\cubed} \times (\frac{\SI{1}{\deci\metre}}{\SI{10}{\centi\metre}})^3 \\ + &= \SI{0.09855}{\mole\per\deci\metre\cubed} \times \SI{200.00e-3}{\deci\metre\cubed} \\ + &= \SI{0.01971}{\mole} + \end{aligned} +\end{displaymath} + +Since: +\begin{displaymath} + \begin{aligned} + \text{Amount \si{\mole}} &= \frac{\text{Mass \si{\gram}}}{M_r \text{ \si{\gram\per\mole}}} \\ + M_r \text{ \si{\gram\per\mole}} &= \frac{\text{Mass \si{\gram}}}{\text{Amount \si{\mole}}} \\ + \end{aligned} +\end{displaymath} +Hence: +\begin{displaymath} + \begin{aligned} + M_r \text{ of \ce{HA}} = \frac{\SI{1.8525}{\gram}}{\SI{0.01971}{\mole}} = \SI{93.98}{\gram\per\mole} + \end{aligned} +\end{displaymath} + +\end{document} diff --git a/7a/7a.bcf b/7a/7a.bcf new file mode 100644 index 0000000..c4f19f8 --- /dev/null +++ b/7a/7a.bcf @@ -0,0 +1,2149 @@ + + + + + + output_encoding + ascii + + + input_encoding + ascii + + + debug + 0 + + + mincrossrefs + 2 + + + minxrefs + 2 + + + sortcase + 1 + + + sortupper + 1 + + + + + + + alphaothers + + + + + labelalpha + 0 + + + labelnamespec + shortauthor + author + shorteditor + editor + translator + + + labeltitle + 0 + + + labeltitlespec + shorttitle + title + maintitle + + + labeltitleyear + 0 + + + labeldateparts + 0 + + + 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+ gender + + + + + + + ../bibliographies/additionaltextbooks.bib + + + klein-organic + + diff --git a/7a/7a.pdf b/7a/7a.pdf new file mode 100644 index 0000000..5da13b1 Binary files /dev/null and b/7a/7a.pdf differ diff --git a/7a/7a.run.xml b/7a/7a.run.xml new file mode 100644 index 0000000..5296e39 --- /dev/null +++ b/7a/7a.run.xml @@ -0,0 +1,87 @@ + + + + + + + + + + + + + + + + + + + + + + + + +]> + + + latex + + 7a.bcf + + + 7a.bbl + + + blx-dm.def + blx-compat.def + biblatex.def + verbose.bbx + authortitle.bbx + standard.bbx + verbose.cbx + biblatex.cfg + british.lbx + english.lbx + + + + biber + + biber + 7a + + + 7a.bcf + + + 7a.bbl + + + 7a.bbl + + + 7a.bcf + + + ../bibliographies/additionaltextbooks.bib + + + diff --git a/7a/7a.tex b/7a/7a.tex new file mode 100644 index 0000000..5e5970a --- /dev/null +++ b/7a/7a.tex @@ -0,0 +1,196 @@ +%Document Setup. +\documentclass{article} +\usepackage{graphicx} %Allows import of images. +\usepackage{float} +\usepackage[extreme,mathspacing=normal,leading=normal]{savetrees} %Reduce whitespace. +\usepackage{siunitx} %SI Units formatting. +%\usepackage{vhistory} %Revision History. +\usepackage[version=4]{mhchem} %Chemical Equations. +\usepackage{amsmath} %Mathematical alignments. +\usepackage{amssymb} %Mathematical symbols e.g. therefore. +\usepackage[parfill]{parskip} %Blank lines between paragraphs. +\usepackage[autostyle]{csquotes} +\usepackage{array} %Table centering. +\usepackage[british]{babel} %British localisation. +\usepackage[backend=biber,style=verbose]{biblatex} %Bibliography. + +\numberwithin{equation}{subsection} %Number equations based on their subsection. +\bibliography{../bibliographies/additionaltextbooks} %Use Bibliography of additional textbooks. + +%Document Headings. +\begin{document} +\title{Preparation of Pear Essence (Propyl Acetate) (7A/PPE)} +\author{Sam White} +\date{07/11/2017} +%\date{\vhCurrentDate\\\vhCurrentVersion} +\maketitle + +%\section{Aim} +%To prepare propyl acetate from propan-1-ol and acetic acid and then determine the percentage yield. + +\section{Reaction Mechanism\footcite[Preparation of Esters, p.~1014]{klein-organic} and Overall Equation} +\begin{figure}[H] + \centering + \includegraphics[width=0.75\textwidth]{Mechanism.png} + \caption{Mechanism for reaction \label{fig:mechanism}} +\end{figure} +\begin{figure}[H] + \centering + \includegraphics[width=0.55\textwidth]{Equation.png} + \caption{Overall Equation for Reaction \label{fig:equation}} +\end{figure} + +\section{Results and Analysis} +{\centering Boiling temperature of pure product: \SI{101}{\celsius} + +Mass of pure product: \SI{4.43}{\gram} + +} +%\begin{table}[h] +% \caption{Masses recorded at end of experiment.} +% \centering +% \begin{tabular}{|c|c|} +% \hline +% Item & Mass / \si{\gram} \\ +% \hline +% Empty Sample Bottle and Lid & 11.93 \\ +% \hline +% Filled Sample Bottle and Lid & 16.36 \\ +% \hline +% Mass of Propyl Acetate & 4.43 \\ +% \hline +% \end{tabular} +%\end{table} + +%\begin{equation} \label{eq:ppyl-acte-abbr} +% \ce{CH3CH2CH2OH(l) + CH3COOH(l) <=>[H+] CH3COOCH2CH2CH3(l) + H2O(l)} +%\end{equation} + +\subsection{Yield Calculation} +\begin{displaymath} + \begin{aligned} + \text{Moles of propan-1-ol at start of reaction} &= \frac{\SI{9.6}{\gram}}{(3(12.011) + 8(1.008) + 15.999) \text{ \si{\gram\per\mole}}} \\ + &= \frac{\SI{9.6}{\gram}}{\SI{60.096}{\gram\per\mole}} = \SI{0.16}{\mole} \\ + \text{Moles of acetic acid at start of reaction} &= \frac{\SI{24}{\gram}}{(2(12.011) + 4(1.008) + 2(15.999))\text{ \si{\gram\per\mole}}} \\ + &= \frac{\SI{24}{\gram}}{\SI{60.052}{\gram\per\mole}} = \SI{0.40}{\mole} + \end{aligned} +\end{displaymath} + +From the equation shown in figure~\ref{fig:equation} there is a 1:1 molar ratio between propan-1-ol and acetic acid, hence the acetic acid is in excess. The equation also shows a 1:1 molar ratio between the propan-1-ol and propyl acetate, hence the theoretical amount of propyl acetate produced is \SI{0.16}{\mole}. + +\begin{displaymath} + \begin{aligned} + \therefore \text{Theoretical yield of propyl acetate} &= \SI{0.16}{\mole} \times (5(12.011) + 10(1.008) + 2(15.999)) \text{ \si{\gram\per\mole}} \\ + &= \SI{0.16}{\mole} \times \SI{102.133}{\gram\per\mole} = \SI{16}{\gram} \\ + \therefore \text{Percentage yield} &= \frac{\SI{4.43}{\gram}}{\SI{16}{\gram}} \times \SI{100}{\percent} = \SI{27}{\percent} + \end{aligned} +\end{displaymath} + +This is quite low. This may be due to losses during the purification (e.g. containers were not washed after transfers and some product remained in the filter paper) and a consequence of the reversible nature of the reaction. %The mass of the reactants should have been measured to increase the accuracy and precision of the percentage yield. + +%This could be due to losses during the purification steps performed (such transfer losses since the containers of the product were not washed after transfers and since a fair amount of product remained in the filter paper) as well as due to the reaction not proceeding entirely to completion since it is reversible. In addition the actual masses of the reactants should have been measured at the start of the experiment to allow a more accurate and precise percentage yield to be determined. +\subsection{Spectra} +%\subsubsection{Reactants} +\begin{table}[h] + \caption{IR Spectrum of propan-1-ol.} + \centering + \begin{tabular}{|c|c|c|} + \hline + Wavenumber / \si{\per\centi\metre} & Strength & Assignment \\ + \hline + 2976.7 & Weak & \ce{CH3} Absorption \\ + \hline + 2936.0 & Weak & \ce{C-H2} Absorption \\ + \hline + 2962.3 & Weak & \ce{C-H3} Absorption \\ + \hline + 3319.0 & Weak and Broad & \ce{O-H} Absorption in Alcohol \\ + \hline + \end{tabular} +\end{table} +\begin{table}[h] + \caption{$^1$H NMR Spectrum of propan-1-ol.} + \centering + \begin{tabular}{|c|c|>{\centering}m{2.2cm}|m{7.9cm}|} + \hline + Chemical Shift / ppm & $J$-Coupling & Integral Area & Summary \\ + \hline + Approx. 7.3 & Singlet & Not Integrated & Characteristic for \ce{CDCl3} (Solvent) \\ + \hline + 3.66 & Triplet & 0.99 & Two $\alpha$-protons to alcohol group. Coupled to two protons. \\ + \hline + 2.03 & Singlet & 3.00 & \ce{OH} proton. Exchange decoupled. \\ \cline{1-2} \cline{4-4} + 1.57 & Quintet (Unclear) & (Integrated together) & Additional splitting possibly obscured by adjacent peaks. Coupled to four or five protons. \\ \cline{1-2} \cline{4-4} + 1.00 & Triplet (Small right-hand peak) & & Coupled to two protons. \\ + \hline + \end{tabular} +\end{table} +\begin{table}[h] + \caption{IR Spectrum of acetic acid.} + \centering + \begin{tabular}{|c|c|c|} + \hline + Wavenumber / \si{\per\centi\metre} & Strength & Assignment \\ + \hline + 1703.9 & Strong & \ce{C=O} Absorption close to acid range (1725-1705 \si{\per\centi\metre}) \\ + \hline + 3032.6 & Weak and Broad & \ce{O-H} Absorption close to carboxylic acid range (3000-2500 \si{\per\centi\metre}) \\ + \hline + \end{tabular} +\end{table} +\begin{table}[h] + \caption{$^1$H NMR Spectrum of acetic acid.} + \centering + \begin{tabular}{|c|c|c|c|} + \hline + Chemical Shift / ppm & $J$-Coupling & Integral Area & Summary \\ + \hline + 10.67 & Singlet & 0.90 & Single proton in \ce{-COOH} group. Exchange decoupled. \\ + \hline + Approx. 7.4 & Singlet & Not Integrated & Characteristic for \ce{CDCl3} (Solvent). \\ + \hline + 2.19 & Singlet & 3.00 & Three $\alpha$-protons to carboxyl group. \\ + \hline + \end{tabular} +\end{table} + +%\subsubsection{Product} +\begin{table}[h] + \caption{IR Spectrum of Product.} + \centering + \begin{tabular}{|c|c|c|} + \hline + Wavenumber / \si{\per\centi\metre} & Strength & Assignment \\ + \hline + 1738.0 & Strong & \ce{C=O} Absorption in the ester range (1740-1710 \si{\per\centi\metre}) \\ + \hline + 2882.5 & Weak & \ce{C-H} Absorption \\ + \hline + 2970.5 & Weak & \ce{C-H} Absorption \\ + \hline + \end{tabular} +\end{table} +\begin{table}[h] + \caption{$^1$H NMR Spectrum of Product.} + \centering + \begin{tabular}{|c|c|c|p{7.9cm}|} + \hline + Chemical Shift / ppm & $J$-Coupling & Integral Area & Summary \\ + \hline + Approx. 7.4 & Singlet & 0.030 & Characteristic for \ce{CDCl3} (Solvent) \\ + \hline + 4.14 & Triplet & 1.98 & Two protons (\ce{RCOO-C\underline{H}}). Coupled to two protons. \\ + \hline + 2.17 & Singlet & 3.28 & Three protons in unique environment \\ + \hline + Approx. 1.8 & Quartet (Unclear) & 1.90 & Two protons coupled three or four protons: splitting pattern difficult to interpret. \\ + \hline + 1.06 & Triplet (Small right-hand peak) & 2.75 & Three protons coupled to two protons. \\ + \hline + \end{tabular} +\end{table} +These spectra are consistent with propyl acetate as a product since the starting materials both had a broad peak corresponding to \ce{O-H} absorptions in their IR spectra, however this is absent in the product's IR spectrum. Also the NMR spectrum for the product shows it has four distinct hydrogen environments with the expected chemical shifts and (mostly) the expected splitting pattens for propyl acetate. In the IR spectra the \ce{C=O} absorption has shifted position from being at \SI{1703.9}{\per\centi\metre} in acetic acid to \SI{1738.0}{\per\centi\metre} in the product: this higher wavenumber is expected for the production of an ester. + +%These spectra are consistent with the product made being propyl acetate since the IR spectrum clearly shows the \ce{C=O} bond in the correct range for an ester and appropriate \ce{C-H} bond absorptions while the $^1$H NMR spectrum shows the correct number of environments, appropriate chemical shifts and roughly correct splitting pattens and areas for propyl acetate. The lack of the broad \ce{O-H} peak in the IR spectrum (which is present in both reactants) also indicates the formation of propyl acetate and little/no reactant impurities. The ambiguity in the splitting pattens in the $^1$H NMR spectrum around 1.6 ppm as well as the deviations of the areas of the peaks from the expected values may be due to the presence of impurities in the product mixture and also possibly due to the solvent residual water peak at 1.5 ppm. + +\end{document} diff --git a/7a/Equation.png b/7a/Equation.png new file mode 100755 index 0000000..71ceb1e Binary files /dev/null and b/7a/Equation.png differ diff --git a/7a/Mechanism.png b/7a/Mechanism.png new file mode 100755 index 0000000..51431e4 Binary files /dev/null and b/7a/Mechanism.png differ diff --git a/bibliographies/additionaltextbooks.bib b/bibliographies/additionaltextbooks.bib new file mode 100644 index 0000000..82b6875 --- /dev/null +++ b/bibliographies/additionaltextbooks.bib @@ -0,0 +1,8 @@ +@book{klein-organic, + title = {Organic Chemistry}, + author = {David Klein}, + year = {2015}, + publisher = {Wiley}, + edition = {2} +} + diff --git a/bibliographies/coretextbooks.bib b/bibliographies/coretextbooks.bib new file mode 100644 index 0000000..97636e5 --- /dev/null +++ b/bibliographies/coretextbooks.bib @@ -0,0 +1,35 @@ +@book{housecroft&constable, + title = {Chemistry: An Introduction to Organic, Inorganic and Physical Chemistry}, + author = {Catherine E. Housecroft and Edwin C. Constable}, + year = {2010}, + publisher = {Prentice Hall}, + address = {Harlow}, + edition = {4} +} + +@book{weller-inorganic, + title = {Inorganic Chemistry}, + author = {Mark Weller and Tine Overton and Jonathan Rourke and Fraser Armstrong}, + year = {2010}, + publisher = {Oxford University Press}, + address = {Oxford}, + edition = {6} +} + +@book{clayden-organic, + title = {Organic Chemistry}, + author = {Jonathan Clayden and Nick Greeves and Stuart Warren}, + year = {2012}, + publisher = {Oxford University Press}, + address = {Oxford}, + edition = {2} +} + +@book{atkins-physical, + title = {Physical Chemistry}, + author = {Peter Atkins and Julio de Paula}, + year = {2014}, + publisher = {Oxford University Press}, + address = {Oxford}, + edition = {10} +} diff --git a/bibliographies/reference.bib b/bibliographies/reference.bib new file mode 100644 index 0000000..d4e2040 --- /dev/null +++ b/bibliographies/reference.bib @@ -0,0 +1,8 @@ +@book{crc-handbook, + title={CRC Handbook of Chemistry and Physics}, + editor={W. M. Haynes}, + year={2016}, + publisher={CRC Press}, + address={Boca Raton}, + edition={97} +}