有機化合物の炭素骨格による分類

\documentclass[b5j,9pt]{tetsujsarticle}
\usepackage{tetsuchem}
\pagestyle{fancy}

\begin{document}
\小見出し{有機化合物の炭素骨格による分類}

\begin{center}
\begin{tikzpicture}
\node[draw,rectangle,thick] (0) at (0,0) {有機化合物};
\node[draw,rectangle,thick] (1) at (3,1.5) {鎖式化合物};
\node[draw,rectangle,thick] (2) at (3,0.5) {環式化合物};
\node[draw,rectangle,thick,right] (3) at (5.5,1) {炭素環式化合物};
\coordinate (3の左) at ($(3)+(-1.55,0)$);
\node[draw,rectangle,thick,right] (4) at (5.5,0) {複素環式化合物};
\coordinate (4の左) at ($(4)+(-1.55,0)$);
\node[draw,rectangle,thick,right] (5) at (9.75,1.5) {脂環式化合物};
\coordinate (5の左) at ($(5)+(-1.4,0)$);
\node[draw,rectangle,thick,right] (6) at (9.75,0.5) {芳香族化合物};
\coordinate (6の左) at ($(6)+(-1.4,0)$);
\node[draw,rectangle,thick] (7) at (3,-0.5) {飽和化合物};
\node[draw,rectangle,thick] (8) at (3,-1.5) {不飽和化合物};
\node[left,yshift=3pt] at (1.75,0.5) {\texthtbi{yes}};
\node[left,yshift=-3pt] at (1.75,1.5) {\texthtbi{no}};
\node[left,yshift=-3pt] at (5.25,1) {\texthtbi{yes}};
\node[left,yshift=3pt] at (5.25,0) {\texthtbi{no}};
\node[left,yshift=3pt] at (9.5,0.5) {\texthtbi{yes}};
\node[left,yshift=-3pt] at (9.5,1.5) {\texthtbi{no}};
\node[left,yshift=3pt] at (1.5,-1.5) {\texthtbi{yes}};
\node[left,yshift=-3pt] at (1.5,-0.5) {\texthtbi{no}};
\draw (0) |- (1.75,1);
\draw (1.75,1) |- (1);
\draw (1.75,1) |- (2);
\draw (3) -- (3の左) -- (4の左) -- (4);
\draw (2) -- (2 -| 3の左);
\draw (5) -- (5の左) -- (6の左) -- (6);
\draw (3) -- (3 -| 5の左);
\draw (0) |- (1.5,-1);
\draw (7) -- (1.5,-0.5) -- (1.5,-1.5) -- (8);
\node[draw,densely dashed,line width=2pt,ellipse callout,callout relative pointer={(0.7cm,-0.5cm)},inner ysep=0.25cm] at (-0.5,2.15) {\small 分子内に環状構造を持つか};
\node[draw,densely dashed,line width=2pt,ellipse callout,callout relative pointer={(0cm,-2.1cm)},inner ysep=0.25cm] at (4.3,3.25) {\small 環が炭素だけで構成されているか};
\node[draw,densely dashed,line width=2pt,ellipse callout,callout relative pointer={(-0.7cm,-1cm)}] at (9.5,2.6) {\small ベンゼン環\scalebox{0.75}{\benzene}を含むか};
\node[draw,densely dashed,line width=2pt,ellipse callout,callout relative pointer={(0.7cm,0.5cm)},inner ysep=0.25cm] at (-0.75,-2.15) {\small 二重結合・三重結合があるか};
\end{tikzpicture}
\end{center}

\br1
\小見出し{アルカンの沸点・融点の変化}

\begin{center}
\begin{tikzpicture}
\draw[thick,-latex] (0,0) -- (15,0) node[right] {炭素数};
\draw[help lines] (0,-225/60) grid[xstep=1cm,ystep=1.66cm] (14.75,4.75);
\draw[thick,-latex] (0,-225/60) -- (0,5) node[above] {温度\〔\DegC〕};
\node[left] at (0,-3.33) {$-200$};
\node[left] at (0,-1.66) {$-100$};
\node[left] at (0,0) {$0$};
\node[left] at (0,1.66) {$100$};
\node[left] at (0,3.33) {$200$};
\node[anchor=south east] at (1,0) {1};
\node[anchor=south east] at (2,0) {2};
\node[anchor=south east] at (3,0) {3};
\node[anchor=south east] at (4,0) {4};
\node[anchor=south east] at (5,0) {5};
\node[anchor=south east] at (6,0) {6};
\node[anchor=south east] at (7,0) {7};
\node[anchor=south east] at (8,0) {8};
\node[anchor=south east] at (9,0) {9};
\node[anchor=south east] at (10,0) {10};
\node[anchor=south east] at (11,0) {11};
\node[anchor=south east] at (12,0) {12};
\node[anchor=south east] at (13,0) {13};
\node[anchor=south east] at (14,0) {14};
\node (c1b) at (1, -161.6/60) {};
\node (c2b) at (2, -89/60) {};
\node (c3b) at (3, -42.1/60) {};
\node (c4b) at (4, -0.5/60) {};
\node (c5b) at (5, 36.07/60) {};
\node (c6b) at (6, 69/60) {};
\node (c7b) at (7, 98/60) {};
\node (c8b) at (8, 126/60) {};
\node (c9b) at (9, 150.8/60) {};
\node (c10b) at (10, 174.2/60) {};
\node (c11b) at (11, 196/60) {};
\node (c12b) at (12, 215/60) {};
\node (c13b) at (13, 234/60) {};
\node (c14b) at (14, 254/60) {};
\fill (c1b) circle (4pt) (c2b) circle (4pt) (c3b) circle (4pt) (c4b) circle (4pt) (c5b) circle (4pt) (c6b) circle (4pt) (c7b) circle (4pt) (c8b) circle (4pt) (c9b) circle (4pt) (c10b) circle (4pt) (c11b) circle (4pt) (c12b) circle (4pt) (c13b) circle (4pt) (c14b) circle (4pt);
\draw[line width=2pt] (c1b) -- (c2b) -- (c3b) -- (c4b) -- (c5b) -- (c6b) -- (c7b) -- (c8b) -- (c9b) -- (c10b) -- (c11b) -- (c12b) -- (c13b) -- (c14b) node[above,yshift=5pt] {\parboxx{\baselineskip=0pt 直鎖アルカン\\\hfil の沸点}};
\node (c1m) at (1, -182.5/60) {};
\node (c2m) at (2, -183/60) {};
\node (c3m) at (3, -189.7/60) {};
\node (c4m) at (4, -138/60) {};
\node (c5m) at (5, -129/60) {};
\node (c6m) at (6, -95/60) {};
\node (c7m) at (7, -91/60) {};
\node (c8m) at (8, -56.8/60) {};
\node (c9m) at (9, -51/60) {};
\node (c10m) at (10, -29.7/60) {};
\node (c11m) at (11, -26/60) {};
\node (c12m) at (12, -12/60) {};
\node (c13m) at (13, -5/60) {};
\node (c14m) at (14, 6/60) {};
\draw[fill=white] (c1m) circle (4pt);
\draw[fill=black!70!white] (c2m) circle (4pt);
\draw[fill=white] (c3m) circle (4pt);
\draw[fill=black!70!white] (c4m) circle (4pt);
\draw[fill=white] (c5m) circle (4pt);
\draw[fill=black!70!white] (c6m) circle (4pt);
\draw[fill=white] (c7m) circle (4pt);
\draw[fill=black!70!white] (c8m) circle (4pt);
\draw[fill=white] (c9m) circle (4pt);
\draw[fill=black!70!white] (c10m) circle (4pt);
\draw[fill=white] (c11m) circle (4pt);
\draw[fill=black!70!white] (c12m) circle (4pt);
\draw[fill=white] (c13m) circle (4pt);
\draw[fill=black!70!white] (c14m) circle (4pt);
\draw[line width=2pt] (c1m) -- (c2m) -- (c3m) -- (c4m) -- (c5m) -- (c6m) -- (c7m) -- (c8m) -- (c9m) -- (c10m) -- (c11m) -- (c12m) -- (c13m) -- (c14m) node[below,xshift=5pt,yshift=-5pt] {\parboxx{\baselineskip=0pt 直鎖アルカン\\\hfil の融点}};
\end{tikzpicture}
\end{center}

\br1
\小見出し{トランス付加}

\begin{center}
\begin{tikzpicture}
\fill[fill=black!35!white] (0.8,0.6) -- (1.2,-0.55) -- (-1.2,-0.55) -- (-0.8,0.6) --cycle;
\node at (0,0) {\chemfig{C(<[:-150,1.14])(>:[3]) =[,1.14] C(<[:-30,1.14])(>:[1])}};
\node at (1,1) {\chemfig{Br{\hamidasi(0zw,0.15zw)[L]{${}^{\delta +}$}} -[,0.9,,,color=white] -[,1.14] Br{\hamidasi(0zw,0.15zw)[L]{${}^{\delta -}$}}}};
\draw[decorate,decoration={snake,amplitude=0.4mm,segment length=0.8mm,post length=0mm}] (1.13,1.15) -- (1.13,0.85);
\draw[-stealth] (0.2,1) .. controls (0,0.8) and (0,0.4) .. (0,0.2);
\draw[decorate,decoration={snake,amplitude=0.2mm,segment length=0.4mm,post length=0mm}] (0,0.1) -- (0,-0.04);
\draw[->] (1.4,0) -- (2,0);
\node at (3.75,0) {\chemfig{C(<[:-150,1.14])(>:[:150])(-[:60,1.14]Br{\hamidasi(-0.85zw,0.65zw)[L]{${}^{+}$}}?) -[,1.14] C?(<[:-30,1.14])(>:[:30])}\ihspace{0.5zw}\ce{ + Br-}};
\node at (3.2,-0.8) {ブロモニウムイオン};
\draw[->] (5.6,0) -- (6.2,0);
\node at (7.5,0) {\chemfig{C(<[:-125,1.14])(>:[:-160])(-[:100,1.14]Br) -[,1.14] C(<[:20,1.14])(>:[:55])(-[:-80,1.14]Br)}};
\end{tikzpicture}
\end{center}

\br1
\小見出し{シス付加}

\begin{center}
\begin{tikzpicture}
\fill[fill=black!35!white] (-1,0) -- (1,0) arc(0:180:1 and 0.5);
\node at (0,-0.3) {金属表面};
\draw (0.35,0.2) -- (0.35,0.7) node[above] {H};
\draw (-0.35,0.2) -- (-0.35,0.7) node[above] {H};
\node at (0,1.5) {\chemfig{C(<[:-150,1.14])(>:[:150]) =[,1.14] C(<[:-30,1.14])(>:[:30])}};
\draw[->] (1.5,0.7) -- (2.1,0.7);
\node at (3.3,0.7) {\chemfig{C(<[:150])(>:[:120,1.2])(-[5,1.14]H) -[,1.14] C(<[:30])(>:[:60,1.2])(-[7,1.14]H)}};
\end{tikzpicture}
\end{center}

\br1
環状アルケンに対する付加反応では，幾何異性体の片方だけが生じることになる。

\begin{center}
$\underset{\raisebox{-1zw}{\hbox{\small シクロペンテン}}}{\chemfig{=[,1.4](-[7]H)>[:55]-[:140,1.6]-[:-140,1.6]<[:-55](-[5]H)}}$\ce{ + Br2 $\cto$}$\underset{\hbox{\small トランス\,\!$-$\,\!$1,\,2-$\,\!ジブロモシクロペンタン}}{\chemfig{-[,1.7,,,line width=3pt](-[:-70,1.2]Br)(-[:70,1.55]H)>[:55]-[:160,1.5]-[:-160,1.5]<[:-55](-[:-110]H)(-[:110,1.75]Br)}}$\ihspace{1zw}（\←~トランス付加。シス形は生じない。）

\br{0.25}
※線の交点（五角形の頂点）に炭素原子がある\ihspace{15zw}

\br{0.5}
$\underset{\hbox{\small $1,\,2-$\,\!ジメチルシクロヘキセン}}{\chemfig{(>[:140]-[:40]?)(-[5]CH3)=[,1.4](>[:40]-[:140]?)(-[7]CH3)}}$\ce{ + H2 ->C[][Pt] }$\underset{\hbox{\small シス\,\!$-1,\,2-$\,\!ジメチルシクロヘキサン}}{\chemfig{(>[:140]-[:40]?)(-[:110,1.75]CH3)(-[5]H)-[,1.4,,,line width=3pt](>[:40]-[:140]?)(-[:70,1.75]CH3)(-[7]H)}}$\ihspace{1zw}（\←~シス付加。トランス形は生じない。）
\end{center}

\br1
\小見出し{共鳴安定化エネルギー}

\begin{center}
\begin{tikzpicture}[>=stealth]
\draw[->] (0,0) -- (0,7) node[above] {エネルギー};
\draw (0.5,0.25) -- (10.3,0.25) node[midway,above] {\benzenefig{*6([:-30]------)}};
\draw (0.5,2) -- (3,2) node[midway,above] {\benzenefig{[:-30]*6(-=----)} +\ce{H2}};
\draw (3,3.75) -- (5.5,3.75) node[midway,above] {\benzenefig{[:-30]*6(=-=---)} +\ce{2H2}};
\draw (6,5.5) -- (10.3,5.5) node[midway,above,xshift=-5pt] {$\underset{\hbox{（仮想分子）}}{\chemfig{-[:-60]=[::60,0.5]-[::60]=[::60,0.5]-[::60]=[::60,0.5]}}$+\ce{3H2}};
\draw (7.5,3) -- (10.3,3) node[midway,above,xshift=-10pt] {$\underset{\hbox{（実在分子）}}{\benzene}$+\ce{3H2}};
\draw[->] (1.25,2) -- (1.25,0.25) node[midway,right] {$120\,\kJmol$};
\draw[->] (3.75,3.75) -- (3.75,0.25) node[midway,right,yshift=10pt] {$2\times120\,\kJmol$};
\draw[->] (6.5,5.5) -- (6.5,0.25) node[midway,right,yshift=57pt] {\parboxx{\baselineskip=0pt $3\times120\,\kJmol$\\\hfil（推定値）}};
\draw[->] (8.25,3) -- (8.25,0.25) node[midway,right] {$206\,\kJmol$（実測値）};
\node[right,double arrow,double arrow head extend=0.2cm,fill,rotate=90,scale=0.75] at (10.2,3) {\makebox[8.7zw][l]{}};
\node[right] at (10.4,4.25) {\parboxx{\baselineskip=0pt 共鳴安定化エネルギー\\（非局在化エネルギー）}};
\end{tikzpicture}
\end{center}

\br1
\小見出し{アルコールの酸化}
\begin{center}
\setatomsep{2em}
\chemfig{R - C(-[2]H)(-[6]H) - OH}\ce{ <=>C[-2\H（酸化）][+2\H（還元）]}\chemfig{R - C(-[2]H) = O}\ce{ ->C[+\O（酸化）]}\chemfig{R - C(=[2]O) - OH}

第１級アルコール\ihspace{5zw}アルデヒド\ihspace{5zw}カルボン酸\ihspace{2zw}

\br{0.5}
\chemfig{R - C(-[2]R{\hamidasi[L]{'}})(-[6]H) - OH}\ce{ <=>C[-2\H（酸化）][+2\H（還元）]}\chemfig{R - C(-[2]R{\hamidasi[L]{'}}) = O}\ihspace{11zw}

第２級アルコール\ihspace{6zw}ケトン\ihspace{13zw}

\br{0.5}
\chemfig{R - C(-[2]R{\hamidasi[L]{'}})(-[6]R{\hamidasi[L]{''}}) -OH}\ce{ ->C[~~~~~~~~~~]}酸化されない\ihspace{11zw}

第３級アルコール\ihspace{22zw}
\end{center}

\br1
\小見出し{混成軌道}

\begin{center}
\begin{tikzpicture}[>=stealth]
\draw[->,thick] (-1.5,0,0) -- (1.5,0,0) node[anchor=west] {$y$};
\draw[->,thick] (0,-1.5,0) -- (0,1.5,0) node[anchor=south] {$z$};
\draw[->,thick] (0,0,-1.5) -- (0,0,1.5) node[anchor=north east] {$x$};
\draw[shading=ball,ball color=gray] (0,0,0) .. controls (0.3535,-0.3535,1) and (0.3535,-0.3535,1.25) .. (0,0,1.25) .. controls (-0.3535,0.3535,1.25) and (-0.3535,0.3535,1) .. (0,0,0) .. controls (0.3535,-0.3535,-1) and (0.3535,-0.3535,-1.25) .. (0,0,-1.25) .. controls (-0.3535,0.3535,-1.25) and (-0.3535,0.3535,-1) .. (0,0,0);
\end{tikzpicture}
\begin{tikzpicture}[>=stealth]
\draw[->,thick] (-1.5,0,0) -- (1.5,0,0) node[anchor=west] {$y$};
\draw[->,thick] (0,-1.5,0) -- (0,1.5,0) node[anchor=south] {$z$};
\draw[->,thick] (0,0,-1.5) -- (0,0,1.5) node[anchor=north east] {$x$};
\draw[shading=ball,ball color=gray] (0,0,0) .. controls (1,0.5,0) and (1.25,0.5,0) .. (1.25,0,0) .. controls (1.25,-0.5,0) and (1,-0.5,0) .. (0,0,0) .. controls (-1,0.5,0) and (-1.25,0.5,0) .. (-1.25,0,0) .. controls (-1.25,-0.5,0) and (-1,-0.5,0) .. (0,0,0);
\end{tikzpicture}
\begin{tikzpicture}[>=stealth]
\draw[->,thick] (-1.5,0,0) -- (1.5,0,0) node[anchor=west] {$y$};
\draw[->,thick] (0,-1.5,0) -- (0,1.5,0) node[anchor=south] {$z$};
\draw[->,thick] (0,0,-1.5) -- (0,0,1.5) node[anchor=north east] {$x$};
\draw[shading=ball,ball color=gray] (0,0,0) .. controls (0.5,1,0) and (0.5,1.25,0) .. (0,1.25,0) .. controls (-0.5,1.25,0) and (-0.5,1,0) .. (0,0,0) .. controls (0.5,-1,0) and (0.5,-1.25,0) .. (0,-1.25,0) .. controls (-0.5,-1.25,0) and (-0.5,-1,0) .. (0,0,0);
\end{tikzpicture}
\end{center}


\end{document}