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% Document Info
\author{teganski}
\pdfinfo{
  /Title (organic-chemistry-exam-1.pdf)
  /Creator (Cheatography)
  /Author (teganski)
  /Subject (Organic Chemistry Exam 1 Cheat Sheet)
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    {\parbox{\dimexpr\textwidth-2\fboxsep\relax}{\noindent
        \hspace*{-6pt}\includegraphics[width=5.8cm]{/web/www.cheatography.com/public/images/cheatography_logo.pdf}}
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\begin{tabulary}{11cm}{L}
    \vspace{-2pt}\large{\bf{\textcolor{DarkBackground}{\textrm{Organic Chemistry Exam 1 Cheat Sheet}}}} \\
    \normalsize{by \textcolor{DarkBackground}{teganski} via \textcolor{DarkBackground}{\uline{cheatography.com/211266/cs/45736/}}}
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  \mymulticolumn{2}{p{5.377cm}}{\bf\textcolor{white}{Cheatographer}}  \\
  \vspace{-2pt}teganski \\
  \uline{cheatography.com/teganski} \\
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  \mymulticolumn{1}{p{5.377cm}}{\bf\textcolor{white}{Cheat Sheet}}  \\
   \vspace{-2pt}Published 24th February, 2025.\\
   Updated 2nd March, 2025.\\
   Page {\thepage} of \pageref{LastPage}.
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  Measure your website readability!\\
  www.readability-score.com
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\begin{document}
\raggedright
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\begin{multicols*}{3}

\begin{tabularx}{5.377cm}{p{0.50124 cm} x{0.87717 cm} x{1.42018 cm} x{1.37841 cm} }
\SetRowColor{DarkBackground}
\mymulticolumn{4}{x{5.377cm}}{\bf\textcolor{white}{Known Reaction Pathways}}  \tn
% Row 0
\SetRowColor{LightBackground}
\textasciicircum{}Reaction Type\textasciicircum{} & \textasciicircum{}Name\textasciicircum{} & \textasciicircum{}Functional Outcome\textasciicircum{} & \textasciicircum{}Key Reagents\textasciicircum{} \tn 
% Row Count 4 (+ 4)
% Row 1
\SetRowColor{white}
\mymulticolumn{4}{x{5.377cm}}{{\bf{Oxidation}}} \tn 
% Row Count 5 (+ 1)
% Row 2
\SetRowColor{LightBackground}
 & Alcohol \seqsplit{Oxidation} & 1° OH → \seqsplit{Aldehyde/Carboxylic} acid \{\{nl\}\} 2° OH → Ketone & PCC (mild), CrO\textasciitilde{}3\textasciitilde{}/H\textasciitilde{}2\textasciitilde{}SO\textasciitilde{}4\textasciitilde{} (strong), KMnO\textasciitilde{}4\textasciitilde{} \tn 
% Row Count 10 (+ 5)
% Row 3
\SetRowColor{white}
 & \seqsplit{Ozonolysis} & Cleaves Alkenes → \seqsplit{Aldehydes/Ketones} & 2. O\textasciitilde{}3\textasciitilde{} \{\{nl\}\} 2. (CH\textasciitilde{}3\textasciitilde{})\textasciitilde{}2\textasciitilde{}S or Zn/H\textasciitilde{}2\textasciitilde{}O \tn 
% Row Count 14 (+ 4)
% Row 4
\SetRowColor{LightBackground}
 & \seqsplit{Benzylic} \seqsplit{Oxidation} & Benzylic carbon → Carboxylic acid & KMnO\textasciitilde{}4\textasciitilde{}, heat \tn 
% Row Count 17 (+ 3)
% Row 5
\SetRowColor{white}
\mymulticolumn{4}{x{5.377cm}}{{\bf{Reduction}}} \tn 
% Row Count 18 (+ 1)
% Row 6
\SetRowColor{LightBackground}
 & \seqsplit{Catalytic} \seqsplit{Hydrogenation} & \seqsplit{Alkene/Alkyne} → Alkane & H\textasciitilde{}2\textasciitilde{}, Pt/Pd/Ni \tn 
% Row Count 21 (+ 3)
% Row 7
\SetRowColor{white}
 & \seqsplit{Poisioned} \seqsplit{Hydrogenation} & Alkyne → Cis-Alkene & H\textasciitilde{}2\textasciitilde{}, Lindlar's Catalyst \tn 
% Row Count 24 (+ 3)
% Row 8
\SetRowColor{LightBackground}
 & \seqsplit{Dissolving} Metal \seqsplit{Reduction} & Alkyne → Trans-Alkene & Na, NH\textasciitilde{}3\textasciitilde{} \tn 
% Row Count 28 (+ 4)
% Row 9
\SetRowColor{white}
 & \seqsplit{Carbonyl} \seqsplit{Reduction} & Aldehyde → 1° OH \{\{nl\}\} Ketone → 2° OH & NaBH\textasciitilde{}4\textasciitilde{} or LiAlH\textasciitilde{}4\textasciitilde{} \tn 
% Row Count 32 (+ 4)
\end{tabularx}
\par\addvspace{1.3em}

\vfill
\columnbreak
\begin{tabularx}{5.377cm}{p{0.50124 cm} x{0.87717 cm} x{1.42018 cm} x{1.37841 cm} }
\SetRowColor{DarkBackground}
\mymulticolumn{4}{x{5.377cm}}{\bf\textcolor{white}{Known Reaction Pathways (cont)}}  \tn
% Row 10
\SetRowColor{LightBackground}
\mymulticolumn{4}{x{5.377cm}}{{\bf{Addition}}} \tn 
% Row Count 1 (+ 1)
% Row 11
\SetRowColor{white}
 & \seqsplit{Hydrohalogenation} & Markovnikov addition of X & HX \tn 
% Row Count 4 (+ 3)
% Row 12
\SetRowColor{LightBackground}
 & \seqsplit{Hydration} & Markovnikov addition of OH & H\textasciitilde{}2\textasciitilde{}O, H\textasciitilde{}1\textasciitilde{}SO\textasciitilde{}4\textasciitilde{} \tn 
% Row Count 6 (+ 2)
% Row 13
\SetRowColor{white}
 & \seqsplit{Hydroboration-Oxidation} & \seqsplit{Anti-Markovnikov} addition of OH & 1. BH\textasciitilde{}3\textasciitilde{}, THF \{\{nl\}\} 2. H\textasciitilde{}2\textasciitilde{}O\textasciitilde{}2\textasciitilde{}, NaOH \tn 
% Row Count 9 (+ 3)
% Row 14
\SetRowColor{LightBackground}
 & \seqsplit{Halogenation} & \seqsplit{Anti-Addition} of X-X & X\textasciitilde{}2\textasciitilde{} \tn 
% Row Count 11 (+ 2)
% Row 15
\SetRowColor{white}
 & \seqsplit{Hydrogenation} & Syn-Addition of H-H & H\textasciitilde{}2\textasciitilde{}, Pd/Pt \tn 
% Row Count 13 (+ 2)
% Row 16
\SetRowColor{LightBackground}
\mymulticolumn{4}{x{5.377cm}}{{\bf{Cyclization}}} \tn 
% Row Count 14 (+ 1)
% Row 17
\SetRowColor{white}
 & \seqsplit{Epoxidation} & Alkene → Epoxide & mCPBA \tn 
% Row Count 16 (+ 2)
% Row 18
\SetRowColor{LightBackground}
 & \seqsplit{Halohdrin} \seqsplit{Cyclization} & Halohydrin → Epoxide & X\textasciitilde{}2\textasciitilde{}, H\textasciitilde{}2\textasciitilde{}O to NaOH \tn 
% Row Count 19 (+ 3)
% Row 19
\SetRowColor{white}
\mymulticolumn{4}{x{5.377cm}}{{\bf{Substitution}}} \tn 
% Row Count 20 (+ 1)
% Row 20
\SetRowColor{LightBackground}
 & S\textasciitilde{}N\textasciitilde{}1 & Forms Carbocation; Racemic & Weak nucleophile, Polar protic solvent \tn 
% Row Count 23 (+ 3)
% Row 21
\SetRowColor{white}
 & S\textasciitilde{}N\textasciitilde{}2 & Inversion of \seqsplit{Configuration} & Strong nucleophile, polar aprotic solvent \tn 
% Row Count 27 (+ 4)
% Row 22
\SetRowColor{LightBackground}
\mymulticolumn{4}{x{5.377cm}}{{\bf{Elimination}}} \tn 
% Row Count 28 (+ 1)
% Row 23
\SetRowColor{white}
 & E1 & Carbocation intermediate, Zaitsev's Rule & Weak base, polar protic solvent \tn 
% Row Count 32 (+ 4)
\end{tabularx}
\par\addvspace{1.3em}

\vfill
\columnbreak
\begin{tabularx}{5.377cm}{p{0.50124 cm} x{0.87717 cm} x{1.42018 cm} x{1.37841 cm} }
\SetRowColor{DarkBackground}
\mymulticolumn{4}{x{5.377cm}}{\bf\textcolor{white}{Known Reaction Pathways (cont)}}  \tn
% Row 24
\SetRowColor{LightBackground}
 & E2 & Concerted, \seqsplit{anti-periplanar} & Strong base (NaOEt, NaOMe, tBuOK) \tn 
% Row Count 3 (+ 3)
% Row 25
\SetRowColor{white}
\mymulticolumn{4}{x{5.377cm}}{{\bf{C-C Bond Formation}}} \tn 
% Row Count 4 (+ 1)
% Row 26
\SetRowColor{LightBackground}
 & \seqsplit{Grignard} \seqsplit{Reaction} & Adds R group to carbonyl & RMgX \tn 
% Row Count 7 (+ 3)
% Row 27
\SetRowColor{white}
\mymulticolumn{4}{x{5.377cm}}{{\bf{Protecting Groups}}} \tn 
% Row Count 8 (+ 1)
% Row 28
\SetRowColor{LightBackground}
 & Alcohol \seqsplit{Protection} & ROH → ROTMS & TMSCl, pyridine \tn 
% Row Count 11 (+ 3)
% Row 29
\SetRowColor{white}
 & Alcohol \seqsplit{Deprotection} & ROTMS → ROH & TBAF \tn 
% Row Count 14 (+ 3)
\hhline{>{\arrayrulecolor{DarkBackground}}----}
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\par\addvspace{1.3em}

\begin{tabularx}{5.377cm}{X}
\SetRowColor{DarkBackground}
\mymulticolumn{1}{x{5.377cm}}{\bf\textcolor{white}{Starting Material  → Alkane}}  \tn
% Row 0
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{\textasciicircum{}Name\textasciicircum{}} \tn 
% Row Count 1 (+ 1)
% Row 1
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Radical Halogenation}}} \tn 
% Row Count 2 (+ 1)
% Row 2
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Allylic Bromination}}} \tn 
% Row Count 3 (+ 1)
% Row 3
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Benzylic Bromination}}} \tn 
% Row Count 4 (+ 1)
% Row 4
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Benzylic Oxidation}}} \tn 
% Row Count 5 (+ 1)
\hhline{>{\arrayrulecolor{DarkBackground}}-}
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\par\addvspace{1.3em}

\begin{tabularx}{5.377cm}{X}
\SetRowColor{DarkBackground}
\mymulticolumn{1}{x{5.377cm}}{\bf\textcolor{white}{Starting Material → Alkene}}  \tn
% Row 0
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{\textasciicircum{}Name\textasciicircum{}} \tn 
% Row Count 1 (+ 1)
% Row 1
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Hydrohalogenation \{\{nl\}\} (HX Addition)}}} \tn 
% Row Count 2 (+ 1)
% Row 2
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Hydrodrohalogenation \{\{nl\}\} (HX Addition with Peroxide)}}} \tn 
% Row Count 4 (+ 2)
% Row 3
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Acid-Catalyzed Hydration}}} \tn 
% Row Count 5 (+ 1)
% Row 4
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Oxymercuration-Demurcuration}}} \tn 
% Row Count 6 (+ 1)
% Row 5
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Hydroboration-Oxidation}}} \tn 
% Row Count 7 (+ 1)
% Row 6
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Halogenation \{\{nl\}\} (X\textasciitilde{}2\textasciitilde{} Addition)}}} \tn 
% Row Count 8 (+ 1)
% Row 7
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Halohydrin Formation}}} \tn 
% Row Count 9 (+ 1)
% Row 8
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Hydrogenation}}} \tn 
% Row Count 10 (+ 1)
% Row 9
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Dihydroxylation (Syn)}}} \tn 
% Row Count 11 (+ 1)
% Row 10
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Dihydroxylation (Anti)}}} \tn 
% Row Count 12 (+ 1)
% Row 11
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Ozonlysis}}} \tn 
% Row Count 13 (+ 1)
\hhline{>{\arrayrulecolor{DarkBackground}}-}
\end{tabularx}
\par\addvspace{1.3em}

\begin{tabularx}{5.377cm}{X}
\SetRowColor{DarkBackground}
\mymulticolumn{1}{x{5.377cm}}{\bf\textcolor{white}{Starting Material → Alkyne}}  \tn
% Row 0
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{\textasciicircum{}Name\textasciicircum{}} \tn 
% Row Count 1 (+ 1)
% Row 1
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Hydrohalogenation \{\{nl\}\} (HX Addition)}}} \tn 
% Row Count 2 (+ 1)
% Row 2
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Halogenation (H\textasciitilde{}2\textasciitilde{} Addition)}}} \tn 
% Row Count 3 (+ 1)
% Row 3
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Acid-Catalyzed Hydration}}} \tn 
% Row Count 4 (+ 1)
% Row 4
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Hydroboration-Oxidation}}} \tn 
% Row Count 5 (+ 1)
% Row 5
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Hydrogenation}}} \tn 
% Row Count 6 (+ 1)
% Row 6
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Poisioned Hydrogenation}}} \tn 
% Row Count 7 (+ 1)
% Row 7
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Dissolving Metal Reduction}}} \tn 
% Row Count 8 (+ 1)
% Row 8
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Ozonolysis}}} \tn 
% Row Count 9 (+ 1)
\hhline{>{\arrayrulecolor{DarkBackground}}-}
\end{tabularx}
\par\addvspace{1.3em}

\begin{tabularx}{5.377cm}{X}
\SetRowColor{DarkBackground}
\mymulticolumn{1}{x{5.377cm}}{\bf\textcolor{white}{Starting Material  → Alcohol}}  \tn
% Row 0
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{\textasciicircum{}Name\textasciicircum{}} \tn 
% Row Count 1 (+ 1)
% Row 1
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Oxidation \{\{nl\}\} (\textasciicircum{}Primary → Aldehyde)\textasciicircum{}}}} \tn 
% Row Count 2 (+ 1)
% Row 2
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Oxidation \{\{nl\}\} \textasciicircum{}(Primary → Carboxylic Acid)\textasciicircum{}}}} \tn 
% Row Count 4 (+ 2)
% Row 3
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Williamson Ether Synthesis}}} \tn 
% Row Count 5 (+ 1)
% Row 4
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Protecting Alcohol}}} \tn 
% Row Count 6 (+ 1)
% Row 5
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Deprotecting Alcohols}}} \tn 
% Row Count 7 (+ 1)
% Row 6
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Intramolecular Williamson Ether Synthesis}}} \tn 
% Row Count 8 (+ 1)
\hhline{>{\arrayrulecolor{DarkBackground}}-}
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{\textasciicircum{}{\bf{Secondary → Ketone}}\textasciicircum{} PCC/PDC, Swern, or Jones Oxidation}  \tn 
\hhline{>{\arrayrulecolor{DarkBackground}}-}
\end{tabularx}
\par\addvspace{1.3em}

\begin{tabularx}{5.377cm}{X}
\SetRowColor{DarkBackground}
\mymulticolumn{1}{x{5.377cm}}{\bf\textcolor{white}{Starting Material → Epoxide}}  \tn
% Row 0
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{\textasciicircum{}Name\textasciicircum{}} \tn 
% Row Count 1 (+ 1)
% Row 1
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Acidic Opening}}} \tn 
% Row Count 2 (+ 1)
% Row 2
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Basic Opening}}} \tn 
% Row Count 3 (+ 1)
\hhline{>{\arrayrulecolor{DarkBackground}}-}
\end{tabularx}
\par\addvspace{1.3em}

\begin{tabularx}{5.377cm}{X}
\SetRowColor{DarkBackground}
\mymulticolumn{1}{x{5.377cm}}{\bf\textcolor{white}{Ranking Radical Stability}}  \tn
% Row 0
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{1. Benzylic/Allylic Radicals {\bf{{[}MOST STABLE{]}}}} \tn 
% Row Count 1 (+ 1)
% Row 1
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{2. Tertiary (3°) Radicals} \tn 
% Row Count 2 (+ 1)
% Row 2
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{3. Secondary (2°) Radicals} \tn 
% Row Count 3 (+ 1)
% Row 3
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{4. Primary (1°) Radicals} \tn 
% Row Count 4 (+ 1)
% Row 4
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{5. Methyl Radicals} \tn 
% Row Count 5 (+ 1)
\hhline{>{\arrayrulecolor{DarkBackground}}-}
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{Key Factors Affecting Stability:  \newline {\bf{Resonance Stabilization}} \textasciicircum{}(Allylic \& Benzylic \textgreater{} Non-resonance stablized)\textasciicircum{} \newline {\bf{Hyperconjugation}} \{\{nl\}\} \textasciicircum{}(More alkyl groups donate electron density)\textasciicircum{} \newline {\bf{Inductive Effects}} \{\{nl\}\} \textasciicircum{}(Electron-withdrawing groups destabilize)\textasciicircum{}}  \tn 
\hhline{>{\arrayrulecolor{DarkBackground}}-}
\end{tabularx}
\par\addvspace{1.3em}

\begin{tabularx}{5.377cm}{X}
\SetRowColor{DarkBackground}
\mymulticolumn{1}{x{5.377cm}}{\bf\textcolor{white}{Arrow Pushing in Radical Reactions}}  \tn
% Row 0
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Fishhook Arrows}} → movement of 1 electron} \tn 
% Row Count 1 (+ 1)
% Row 1
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Initiation}} → arrows depict homolytic cleavage} \tn 
% Row Count 3 (+ 2)
% Row 2
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Propagation}} → 1 radical reacts to form another} \tn 
% Row Count 5 (+ 2)
% Row 3
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Termination}} → 2 radicals combine to form a stable molecule} \tn 
% Row Count 7 (+ 2)
\hhline{>{\arrayrulecolor{DarkBackground}}-}
\end{tabularx}
\par\addvspace{1.3em}

\begin{tabularx}{5.377cm}{x{1.8308 cm} p{0.4577 cm} x{2.2885 cm} }
\SetRowColor{DarkBackground}
\mymulticolumn{3}{x{5.377cm}}{\bf\textcolor{white}{Number of Unique Products}}  \tn
% Row 0
\SetRowColor{LightBackground}
{\bf{NBS}} \{\{nl\}\} \textasciicircum{}(Allylic Bromination)\textasciicircum{} &  & {\bf{Cl₂/hv}} \{\{nl\}\} \textasciicircum{}(Radical Chlorination)\textasciicircum{} \tn 
% Row Count 3 (+ 3)
% Row 1
\SetRowColor{white}
{\emph{Selective}} \{\{nl\}\} \textasciicircum{}Only abstracts the {\bf{allylic hydrogen}}\textasciicircum{} &  & {\emph{Less selective}} \{\{nl\}\} \textasciicircum{}attacks {\bf{all possible C-H bonds}}\textasciicircum{} \tn 
% Row Count 7 (+ 4)
% Row 2
\SetRowColor{LightBackground}
Favors one major product due to resonance stabilization &  & {\bf{More radical products}} due to no preference \tn 
% Row Count 11 (+ 4)
% Row 3
\SetRowColor{white}
Highly Selective → Major product at most stable radical site &  & Non-selective → Multiple products \tn 
% Row Count 15 (+ 4)
\hhline{>{\arrayrulecolor{DarkBackground}}---}
\end{tabularx}
\par\addvspace{1.3em}

\begin{tabularx}{5.377cm}{x{1.55618 cm} x{1.46464 cm} x{1.55618 cm} }
\SetRowColor{DarkBackground}
\mymulticolumn{3}{x{5.377cm}}{\bf\textcolor{white}{Synthesis}}  \tn
% Row 0
\SetRowColor{LightBackground}
{\bf{ 1. Identify Target Molecule}} & Determine functional groups \& backbone & {\emph{What is the most complex feature?}} \tn 
% Row Count 4 (+ 4)
% Row 1
\SetRowColor{white}
{\bf{2. Work Backward}} & Identify possible precursors & {\emph{What reactions introduce those functional groups?}} \tn 
% Row Count 8 (+ 4)
% Row 2
\SetRowColor{LightBackground}
{\bf{3. Select Key Transformations}} & Use known reaction pathways & {\emph{Oxidation, Reduction, Substitution, Addition, Elimination}} \tn 
% Row Count 13 (+ 5)
% Row 3
\SetRowColor{white}
{\bf{4. Consider Stereo- \& Regio- Chemistry}} & Identify selective pathways & {\emph{Anti vs Syn, Markovnikov vs Anti-Markovnikov}} \tn 
% Row Count 17 (+ 4)
% Row 4
\SetRowColor{LightBackground}
{\bf{5. Check for Side Reactions}} & Minimize unwanted byproducts & {\emph{Use protecting groups if necessary}} \tn 
% Row Count 20 (+ 3)
% Row 5
\SetRowColor{white}
{\bf{6. Verify Pathway}} & Double check feasibility \& efficiency & {\emph{Are reagents compatible? Do steps make sense?}} \tn 
% Row Count 24 (+ 4)
\hhline{>{\arrayrulecolor{DarkBackground}}---}
\end{tabularx}
\par\addvspace{1.3em}

\begin{tabularx}{5.377cm}{x{1.32733 cm} x{1.8308 cm} x{1.41887 cm} }
\SetRowColor{DarkBackground}
\mymulticolumn{3}{x{5.377cm}}{\bf\textcolor{white}{Starting Material → Ether}}  \tn
% Row 0
\SetRowColor{LightBackground}
\textasciicircum{}Name\textasciicircum{} & \textasciicircum{}Reagents\textasciicircum{} & \textasciicircum{}Functional Outcome\textasciicircum{} \tn 
% Row Count 2 (+ 2)
% Row 1
\SetRowColor{white}
{\bf{Acidic Cleavage}} & xsHX \textasciicircum{}(HBr or HI)\textasciicircum{} in heat & Alkyl Halide \tn 
% Row Count 4 (+ 2)
\hhline{>{\arrayrulecolor{DarkBackground}}---}
\end{tabularx}
\par\addvspace{1.3em}

\begin{tabularx}{5.377cm}{X}
\SetRowColor{DarkBackground}
\mymulticolumn{1}{x{5.377cm}}{\bf\textcolor{white}{Oxidation State of Carbons}}  \tn
% Row 0
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{C-H bond}} → carbon gains {\bf{-1}} per hydrogen} \tn 
% Row Count 1 (+ 1)
% Row 1
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{C-C bond}} → no change {\bf{(0)}}} \tn 
% Row Count 2 (+ 1)
% Row 2
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{C-X bond}} → carbon loses {\bf{+1}} per electronegative atom} \tn 
% Row Count 4 (+ 2)
\hhline{>{\arrayrulecolor{DarkBackground}}-}
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{The {\bf{oxidation state}} of a carbon atom depends on its {\bf{bonds}} to atoms of different electronegativities}  \tn 
\hhline{>{\arrayrulecolor{DarkBackground}}-}
\end{tabularx}
\par\addvspace{1.3em}

\begin{tabularx}{5.377cm}{x{1.2531 cm} p{0.4177 cm} x{2.0885 cm} p{0.4177 cm} }
\SetRowColor{DarkBackground}
\mymulticolumn{4}{x{5.377cm}}{\bf\textcolor{white}{NMR}}  \tn
% Row 0
\SetRowColor{LightBackground}
{\bf{\textasciicircum{}1\textasciicircum{}H NMR}} \{\{nl\}\} &  & {\bf{\textasciicircum{}13\textasciicircum{}C NMR}} \{\{nl\}\} &  \tn 
% Row Count 2 (+ 2)
% Row 1
\SetRowColor{white}
{\emph{\textasciicircum{}Chemical Shift Trends\textasciicircum{}}} &  & {\emph{\textasciicircum{}Chemical Shift Trends\textasciicircum{}}} &  \tn 
% Row Count 5 (+ 3)
% Row 2
\SetRowColor{LightBackground}
{\bf{0-2 ppm}} → Alkane &  & {\bf{0-50 ppm}} → Alkane &  \tn 
% Row Count 7 (+ 2)
% Row 3
\SetRowColor{white}
{\bf{2-3 ppm}} → Allylic, benzylic, alkynyl &  & {\bf{50-100 ppm}} → Alcohol, ether, alkynes &  \tn 
% Row Count 11 (+ 4)
% Row 4
\SetRowColor{LightBackground}
{\bf{4-6 ppm}} → Alkene &  & {\bf{100-150 ppm}} → Aromatic, alkene &  \tn 
% Row Count 13 (+ 2)
% Row 5
\SetRowColor{white}
{\bf{6-8 ppm}} → Aromatic &  & {\bf{150-200 ppm}} Carbonyl (ketone, aldehyde, carboxylic acid) &  \tn 
% Row Count 16 (+ 3)
% Row 6
\SetRowColor{LightBackground}
\mymulticolumn{4}{x{5.377cm}}{{\bf{9-10 ppm}} →\{\{nl\}\}  Aldehyde} \tn 
% Row Count 17 (+ 1)
% Row 7
\SetRowColor{white}
\mymulticolumn{4}{x{5.377cm}}{{\bf{10-12 ppm}} →\{\{nl\}\} Carboxylic acid (broad)} \tn 
% Row Count 18 (+ 1)
\hhline{>{\arrayrulecolor{DarkBackground}}----}
\SetRowColor{LightBackground}
\mymulticolumn{4}{x{5.377cm}}{{\bf{Splitting Patterns}} \textasciicircum{}(n+1 rule)\textasciicircum{} \newline {\bf{Singlet}} → no adjacent protons \newline {\bf{Doublet}} → 1 adjacent proton \newline {\bf{Triplet}} → 2 adjacent protons}  \tn 
\hhline{>{\arrayrulecolor{DarkBackground}}----}
\end{tabularx}
\par\addvspace{1.3em}

\begin{tabularx}{5.377cm}{X}
\SetRowColor{DarkBackground}
\mymulticolumn{1}{x{5.377cm}}{\bf\textcolor{white}{IR Spectroscopy}}  \tn
% Row 0
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\emph{\textasciicircum{}Key Peaks\textasciicircum{}}}} \tn 
% Row Count 1 (+ 1)
% Row 1
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{O-H (Alcohol)}} → 3200-3600 cm\textasciicircum{}-1\textasciicircum{} (broad)} \tn 
% Row Count 2 (+ 1)
% Row 2
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{C-H (Alkanes)}} → 2800-3000 cm\textasciicircum{}-1\textasciicircum{}} \tn 
% Row Count 3 (+ 1)
% Row 3
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{C=O (Carbonyls)}} → \textasciitilde{}1700 cm\textasciicircum{}-1\textasciicircum{}} \tn 
% Row Count 4 (+ 1)
% Row 4
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{C=C (Alkene)}} → \textasciitilde{}1650 cm\textasciicircum{}-1\textasciicircum{}} \tn 
% Row Count 5 (+ 1)
% Row 5
\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{C≡C, C≡N}} → \textasciitilde{}2100-2200 cm\textasciicircum{}-1\textasciicircum{}} \tn 
% Row Count 6 (+ 1)
\hhline{>{\arrayrulecolor{DarkBackground}}-}
\end{tabularx}
\par\addvspace{1.3em}

\begin{tabularx}{5.377cm}{x{2.4885 cm} x{2.4885 cm} }
\SetRowColor{DarkBackground}
\mymulticolumn{2}{x{5.377cm}}{\bf\textcolor{white}{Terms to Know}}  \tn
% Row 0
\SetRowColor{LightBackground}
{\bf{Markovnikov's Rule}} → {\emph{addition reactions}} proton added to the {\emph{carbon}} with the {\bf{most}} {\emph{hydrogen}} atoms attached & {\bf{Geminal}} → 2 atoms bonded to the {\emph{same side}} of the carbon \tn 
% Row Count 6 (+ 6)
% Row 1
\SetRowColor{white}
{\bf{Anti-Markovnivkov's Rule}} → {\emph{addition reactions}} proton added to the {\emph{carbon}} with the {\bf{least}} {\emph{hydrogen}} atoms attached & {\bf{Vicinal}} → 2 atoms bonded to {\emph{same}} carbon \tn 
% Row Count 13 (+ 7)
% Row 2
\SetRowColor{LightBackground}
{\bf{Zaitsev's Rule}} → {\emph{elimination reaction}}, major product is the {\bf{more stable}} alkene with the {\bf{highly substituted}} double bond & {\bf{Syn-Addition}} → added to {\emph{same side}} of compound \tn 
% Row Count 20 (+ 7)
% Row 3
\SetRowColor{white}
{\bf{E/Z System}} → Prioritize the 2 groups attached to each carbon relative to one another. \{\{nl\}\} {\emph{Higher}} priority groups are: \{\{nl\}\} {\bf{cis/same side}} → {\bf{Z}} \{\{nl\}\} {\bf{trans/opposite sides}} → {\bf{E}} & {\bf{Anti-Addition}} → added to {\emph{different sides }}of compounds \tn 
% Row Count 31 (+ 11)
\hhline{>{\arrayrulecolor{DarkBackground}}--}
\end{tabularx}
\par\addvspace{1.3em}

\begin{tabularx}{5.377cm}{X}
\SetRowColor{DarkBackground}
\mymulticolumn{1}{x{5.377cm}}{\bf\textcolor{white}{Formation of Grignard Reagent}}  \tn
% Row 0
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{Mg(0); THF (or Et\textasciitilde{}2\textasciitilde{}O)} \tn 
% Row Count 1 (+ 1)
\hhline{>{\arrayrulecolor{DarkBackground}}-}
\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{Forms Gignard Reagent {\bf{(RMgX)}} \newline Can be used to form C-C bonds}  \tn 
\hhline{>{\arrayrulecolor{DarkBackground}}-}
\end{tabularx}
\par\addvspace{1.3em}

\begin{tabularx}{5.377cm}{x{1.2531 cm} p{0.4177 cm} x{2.0885 cm} p{0.4177 cm} }
\SetRowColor{DarkBackground}
\mymulticolumn{4}{x{5.377cm}}{\bf\textcolor{white}{Substitution Reactions}}  \tn
% Row 0
\SetRowColor{LightBackground}
S\textasciitilde{}N\textasciitilde{}1 \textasciicircum{}(Unimolecular)\textasciicircum{} &  & S\textasciitilde{}N\textasciitilde{}2 \textasciicircum{}(Bimolecular)\textasciicircum{} &  \tn 
% Row Count 2 (+ 2)
% Row 1
\SetRowColor{white}
{\bf{Mechanism}} → Two-step; carbocation formation, \seqsplit{nucleophilic} attack &  & {\bf{Mechanism}} → One-step; backside attack &  \tn 
% Row Count 8 (+ 6)
% Row 2
\SetRowColor{LightBackground}
{\bf{Rate}} → Dependent {\emph{only}} on substrate \{\{nl\}\} \textasciicircum{}rate=k{[}R-X{]}\textasciicircum{} &  & {\bf{Rate}} → Dependent on {\emph{both}} substrate \& nucleophile \{\{nl\}\} \textasciicircum{}rate=k{[}R-X{]}{[}Nu-{]}\textasciicircum{} &  \tn 
% Row Count 14 (+ 6)
% Row 3
\SetRowColor{white}
{\bf{Stereochemistry}} → Racemic mixture &  & {\bf{Stereochemistry}} → Inversion of configuration &  \tn 
% Row Count 18 (+ 4)
% Row 4
\SetRowColor{LightBackground}
{\bf{Preferred Conditions}} → Weak nucleophile, polar protic solvent &  & {\bf{Preferred Conditions}} → Strong nucleophile, polar aprotic solvent &  \tn 
% Row Count 24 (+ 6)
% Row 5
\SetRowColor{white}
Tertiary \textgreater{} Secondary \textgreater{} \textasciitilde{}\textasciitilde{}{\emph{Primary}}\textasciitilde{}\textasciitilde{} &  & Methyl \textgreater{} Primary \textgreater{} Secondary \textgreater{} \textasciitilde{}\textasciitilde{}{\emph{Tertiary}}\textasciitilde{}\textasciitilde{} &  \tn 
% Row Count 27 (+ 3)
\hhline{>{\arrayrulecolor{DarkBackground}}----}
\end{tabularx}
\par\addvspace{1.3em}

\begin{tabularx}{5.377cm}{x{1.2531 cm} p{0.4177 cm} x{2.0885 cm} p{0.4177 cm} }
\SetRowColor{DarkBackground}
\mymulticolumn{4}{x{5.377cm}}{\bf\textcolor{white}{Elimination Reactions}}  \tn
% Row 0
\SetRowColor{LightBackground}
{\bf{E1}} \textasciicircum{}(Unimolecular)\textasciicircum{} &  & {\bf{E2}} \textasciicircum{}(Bimolecular)\textasciicircum{} &  \tn 
% Row Count 2 (+ 2)
% Row 1
\SetRowColor{white}
{\bf{Mechanism}} → Two-step; carbocation \seqsplit{intermediate}, base \seqsplit{deprotonates} &  & {\bf{Mechanism}} → One-step; concerted β-H abstraction &  \tn 
% Row Count 8 (+ 6)
% Row 2
\SetRowColor{LightBackground}
{\bf{Rate}} → Dependent {\emph{only}} on substrate &  & {\bf{Rate}} → Dependent on {\emph{both}} substrate and base &  \tn 
% Row Count 12 (+ 4)
% Row 3
\SetRowColor{white}
{\bf{Regiochemistry}} → Zaitsev's Rule \{\{nl\}\} \textasciicircum{}(more substituted alkene favored)\textasciicircum{} &  & {\bf{Regiochemistry}} → Zaitsev's Rule \{\{nl\}\} \textasciicircum{}(unless bulky base → Hofmann product)\textasciicircum{} &  \tn 
% Row Count 19 (+ 7)
% Row 4
\SetRowColor{LightBackground}
{\bf{Stereochemistry}} → Forms most stable alkene &  & {\bf{Stereochemistry}} → Anti-periplanar elimination &  \tn 
% Row Count 23 (+ 4)
% Row 5
\SetRowColor{white}
{\bf{Preferred Conditions}} → Weak base, polar protic solvent &  & {\bf{Preferred Conditions}} → Strong base required &  \tn 
% Row Count 28 (+ 5)
% Row 6
\SetRowColor{LightBackground}
Tertiary \textgreater{} Secondary \textgreater{} \textasciitilde{}\textasciitilde{}{\emph{Primary}}\textasciitilde{}\textasciitilde{} &  & Primary \textgreater{} Secondary \textgreater{} Tertiary \{\{nl\}\} \textasciicircum{}(as long as β-H is anti-periplanar)\textasciicircum{} &  \tn 
% Row Count 32 (+ 4)
\hhline{>{\arrayrulecolor{DarkBackground}}----}
\end{tabularx}
\par\addvspace{1.3em}

\begin{tabularx}{5.377cm}{x{1.14425 cm} x{1.73926 cm} x{1.69349 cm} }
\SetRowColor{DarkBackground}
\mymulticolumn{3}{x{5.377cm}}{\bf\textcolor{white}{Nomenclature}}  \tn
% Row 0
\SetRowColor{LightBackground}
\textasciicircum{}Functional Group\textasciicircum{} & \textasciicircum{}Suffix (Highest Priority)\textasciicircum{} & \textasciicircum{}Prefix (Lowest Priority)\textasciicircum{} \tn 
% Row Count 2 (+ 2)
% Row 1
\SetRowColor{white}
{\bf{Alcohol (-OH)}} & -ol & hydroxy- \tn 
% Row Count 4 (+ 2)
% Row 2
\SetRowColor{LightBackground}
{\bf{Alkyne}} & -yne & alkynyl- \tn 
% Row Count 5 (+ 1)
% Row 3
\SetRowColor{white}
{\bf{Ether (R-O-R')}} & uses parent name & alkoxy- \tn 
% Row Count 7 (+ 2)
% Row 4
\SetRowColor{LightBackground}
{\bf{Epoxide}} & oxirane (cyclic naming) & epoxy- \tn 
% Row Count 9 (+ 2)
\hhline{>{\arrayrulecolor{DarkBackground}}---}
\SetRowColor{LightBackground}
\mymulticolumn{3}{x{5.377cm}}{Key Naming Rules → \{\{nl\}\} \newline Number the longest chain to give {\bf{OH}} the lowest number \{\{nl\}\} \newline Number to give triple bond the {\bf{lowest}} number, unless -OH is present \{\{nl\}\}}  \tn 
\hhline{>{\arrayrulecolor{DarkBackground}}---}
\end{tabularx}
\par\addvspace{1.3em}


% That's all folks
\end{multicols*}

\end{document}