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\author{teganski}
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  /Title (organic-chemistry-exam-1.pdf)
  /Creator (Cheatography)
  /Author (teganski)
  /Subject (Organic Chemistry Exam 1 Cheat Sheet)
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        \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}Not Yet Published.\\
   Updated 23rd February, 2025.\\
   Page {\thepage} of \pageref{LastPage}.
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  Measure your website readability!\\
  www.readability-score.com
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\begin{document}
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\begin{multicols*}{3}

\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 
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% Row 2
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\mymulticolumn{1}{x{5.377cm}}{3. Secondary (2°) Radicals} \tn 
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\mymulticolumn{1}{x{5.377cm}}{4. Primary (1°) Radicals} \tn 
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% Row 4
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\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{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}
\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{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}}--}
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\begin{tabularx}{5.377cm}{X}
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\mymulticolumn{1}{x{5.377cm}}{\bf\textcolor{white}{Oxidation State of Carbons}}  \tn
% Row 0
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\mymulticolumn{1}{x{5.377cm}}{{\bf{C-H bond}} → carbon gains {\bf{-1}} per hydrogen} \tn 
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% Row 1
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\mymulticolumn{1}{x{5.377cm}}{{\bf{C-C bond}} → no change {\bf{(0)}}} \tn 
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% Row 2
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\mymulticolumn{1}{x{5.377cm}}{{\bf{C-X bond}} → carbon loses {\bf{+1}} per electronegative atom} \tn 
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\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}}-}
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\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}
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\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 
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\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Hydrodrohalogenation \{\{nl\}\} (HX Addition with Peroxide)}}} \tn 
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\mymulticolumn{1}{x{5.377cm}}{{\bf{Acid-Catalyzed Hydration}}} \tn 
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\SetRowColor{LightBackground}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Oxymercuration-Demurcuration}}} \tn 
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\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 
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\mymulticolumn{1}{x{5.377cm}}{{\bf{Halohydrin Formation}}} \tn 
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\mymulticolumn{1}{x{5.377cm}}{{\bf{Hydrogenation}}} \tn 
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\SetRowColor{white}
\mymulticolumn{1}{x{5.377cm}}{{\bf{Dihydroxylation (Syn)}}} \tn 
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% 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}{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}{p{0.4977 cm} p{0.4977 cm} }
\SetRowColor{DarkBackground}
\mymulticolumn{2}{x{5.377cm}}{\bf\textcolor{white}{Starting Material → Alkyne}}  \tn
% Row 0
\SetRowColor{LightBackground}
\mymulticolumn{2}{x{5.377cm}}{} \tn 
% Row Count 0 (+ 0)
\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}


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

\end{document}