«K12/K13» Carbonylverbindungen «PDF», «POD»

0.0.0.1 ↑ Carbonylverbindungen

Funktionelle Gruppe:

\setlength{\arraycolsep}{0pt} \begin{array}{ccccc} {} & ^{/} & \text{O} & ^{\backslash} & \\ {} & & \vert\vert{} & & \\ {} & & \text{C} & & \\ {} & ^{/} & & ^{\backslash} & \\ {} \text{R}_1 & & & & \text{R}_2 \end{array}$\begin{array}{ccccc}\hfill \hfill & \hfill {}^{∕}\hfill & \hfill \text{O}\hfill & \hfill {}^{\setminus }\hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \mid \mid \hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \text{C}\hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill {}^{∕}\hfill & \hfill \hfill & \hfill {}^{\setminus }\hfill & \hfill \hfill \\ \hfill {\text{R}}_1\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill {\text{R}}_2\hfill \end{array}$

1. Alkanale (Aldehyde)

   \setlength{\arraycolsep}{0pt} \begin{array}{ccccc} {} & ^{/} & \text{O} & ^{\backslash} & \\ {} & & \vert\vert{} & & \\ {} & & \text{C} & & \\ {} & ^{/} & & ^{\backslash} & \\ {} \text{H} & & & & \text{R}_2 \end{array}$\begin{array}{ccccc}\hfill \hfill & \hfill {}^{∕}\hfill & \hfill \text{O}\hfill & \hfill {}^{\setminus }\hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \mid \mid \hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \text{C}\hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill {}^{∕}\hfill & \hfill \hfill & \hfill {}^{\setminus }\hfill & \hfill \hfill \\ \hfill \text{H}\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill {\text{R}}_2\hfill \end{array}$

   a)

   Beispiele

   Name	Struk­tur­for­mel	Siedepunkt (°C)	Was­ser­lös­lich­keit	Bedeutung und Verwendung
   Methanal (Formaldehyd)	\setlength{\arraycolsep}{0pt} \begin{array}{cccccc} {} \text{H} & & & & & \\ {} & \backslash{} & & & & \backslash{} \\ {} & & \text{C} & = & \text{O} & \\ {} & / & & & & / \\ {} \text{H} & & & & & \end{array}$\begin{array}{cccccc}\hfill \text{H}\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \setminus \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \setminus \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \text{C}\hfill & \hfill =\hfill & \hfill \text{O}\hfill & \hfill \hfill \\ \hfill \hfill & \hfill ∕\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill ∕\hfill \\ \hfill \text{H}\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill \end{array}$	-19	+	Konservation organischer Stoffe, Desinfektionsmittel
   Ethanal (Acetaldehyd)	\setlength{\arraycolsep}{0pt} \begin{array}{ccccccc} {} & & & & \text{H} & & \text{H} \\ {} & & & / & & / & \\ {} \text{H} & - & \text{C} & - & \text{C} & & \\ {} & & & \backslash{} & & \backslash\!\backslash{} & \\ {} & & & & \text{H} & & \underline{\text{O}}| \end{array}$\begin{array}{ccccccc}\hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \text{H}\hfill & \hfill \hfill & \hfill \text{H}\hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill ∕\hfill & \hfill \hfill & \hfill ∕\hfill & \hfill \hfill \\ \hfill \text{H}\hfill & \hfill -\hfill & \hfill \text{C}\hfill & \hfill -\hfill & \hfill \text{C}\hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \setminus \hfill & \hfill \hfill & \hfill \setminus \setminus \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \text{H}\hfill & \hfill \hfill & \hfill \underset{¯}{\text{O}}\mid \hfill \end{array}$	21	+	Zwischenprodukt beim Alkoholabbau
   Propanal (Propionaldehyd)	\setlength{\arraycolsep}{0pt} \begin{array}{cccccccc} {} & & & & & & & \overline{\text{O}}| \\ {} & | & & | & & & /\!/ & \\ {} - & \text{C} & - & \text{C} & - & \text{C} & & \\ {} & | & & | & & & \backslash{} & \\ {} & & & & & & & \text{H} \end{array}$\begin{array}{cccccccc}\hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \overline{\text{O}}\mid \hfill \\ \hfill \hfill & \hfill \mid \hfill & \hfill \hfill & \hfill \mid \hfill & \hfill \hfill & \hfill \hfill & \hfill ∕∕\hfill & \hfill \hfill \\ \hfill -\hfill & \hfill \text{C}\hfill & \hfill -\hfill & \hfill \text{C}\hfill & \hfill -\hfill & \hfill \text{C}\hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \mid \hfill & \hfill \hfill & \hfill \mid \hfill & \hfill \hfill & \hfill \hfill & \hfill \setminus \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \text{H}\hfill \end{array}$	48	-	Kunst- und Duftstoffe, Arzneimittel (XXX)
   Hexanal (Capronaldehyd)	\text{C}_5\text{H}_{11}{-}{ \setlength{\arraycolsep}{0pt} \begin{array}{ccc} {} & & \text{H} \\ {} & / & \\ {} \text{C} & & \\ {} & \backslash\!\backslash{} & \\ {} & & \underline{\text{O}}| \end{array} }${\text{C}}_5{\text{H}}_{11}-\begin{array}{ccc}\hfill \hfill & \hfill \hfill & \hfill \text{H}\hfill \\ \hfill \hfill & \hfill ∕\hfill & \hfill \hfill \\ \hfill \text{C}\hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \setminus \setminus \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \underset{¯}{\text{O}}\mid \hfill \end{array}$	130	-	Anstrichmittel (XXX)
   Benz­al­de­hyd	[Ben­zol­grup­pe mit \setlength{\arraycolsep}{0pt} \begin{array}{cccc} {} & & & \overline{\text{O}}| \\ {} & & /\!/ & \\ {} - & \text{C} & & \\ {} & & \backslash{} & \\ {} & & & \text{H} \end{array}$\begin{array}{cccc}\hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \overline{\text{O}}\mid \hfill \\ \hfill \hfill & \hfill \hfill & \hfill ∕∕\hfill & \hfill \hfill \\ \hfill -\hfill & \hfill \text{C}\hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \setminus \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \text{H}\hfill \end{array}$ dran]	180	-	Duft- und Aromastoffe

   b)

   Chemische Eigenschaften

   Oxidierbar zu Carbonsäure

   { \setlength{\arraycolsep}{0pt} \begin{array}{cccccc} {} \text{R}_1 & & & & & \\ {} & \backslash{} & & & & \backslash{} \\ {} & & \text{C} & = & \text{O} & \\ {} & / & & & & / \\ {} \text{H} & & & & & \end{array} } + 2\,\text{OH}^- \longrightarrow { \setlength{\arraycolsep}{0pt} \begin{array}{ccccccc} {} & & & & \overline{\text{O}}| & & \\ {} & & & /\!/ & & & \\ {} \text{R}_1 & - & \text{C} & & & & \\ {} & & & \backslash{} & & & \\ {} & & & & \overline{\underline{\text{O}}} & - & \text{H} \end{array} } + \text{H}_2\text{O} + 2\,e^-$\begin{array}{cccccc}\hfill {\text{R}}_1\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \setminus \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \setminus \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \text{C}\hfill & \hfill =\hfill & \hfill \text{O}\hfill & \hfill \hfill \\ \hfill \hfill & \hfill ∕\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill ∕\hfill \\ \hfill \text{H}\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill \end{array}+2{\text{OH}}^{-}\to \begin{array}{ccccccc}\hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \overline{\text{O}}\mid \hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill ∕∕\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill \\ \hfill {\text{R}}_1\hfill & \hfill -\hfill & \hfill \text{C}\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \setminus \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \overline{\underset{¯}{\text{O}}}\hfill & \hfill -\hfill & \hfill \text{H}\hfill \end{array}+{\text{H}}_2\text{O}+2e^{-}$

   → Nachweis: Silberspiegel- oder Fehlingprobe

2. Ketone (Alkanone)

   \setlength{\arraycolsep}{0pt} \begin{array}{ccccc} {} & ^{/} & \text{O} & ^{\backslash} & \\ {} & & \vert\vert{} & & \\ {} & & \text{C} & & \\ {} & ^{/} & & ^{\backslash} & \\ {} \text{R}_1 & & & & \text{R}_2 \end{array}$\begin{array}{ccccc}\hfill \hfill & \hfill {}^{∕}\hfill & \hfill \text{O}\hfill & \hfill {}^{\setminus }\hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \mid \mid \hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \text{C}\hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill {}^{∕}\hfill & \hfill \hfill & \hfill {}^{\setminus }\hfill & \hfill \hfill \\ \hfill {\text{R}}_1\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill {\text{R}}_2\hfill \end{array}$

   \text{R}_1, \text{R}_2 \neq \text{H}${\text{R}}_1,{\text{R}}_2\ne \text{H}$

   a)

   Beispiele

   Propanon (Aceton)

   \setlength{\arraycolsep}{0pt} \begin{array}{ccccc} {} & ^{/} & \text{O} & ^{\backslash} & \\ {} & & \vert\vert{} & & \\ {} & & \text{C} & & \\ {} & ^{/} & & ^{\backslash} & \\ {} \text{H}_3\text{C} & & & & \text{C}\text{H}_3 \end{array}$\begin{array}{ccccc}\hfill \hfill & \hfill {}^{∕}\hfill & \hfill \text{O}\hfill & \hfill {}^{\setminus }\hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \mid \mid \hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \text{C}\hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill {}^{∕}\hfill & \hfill \hfill & \hfill {}^{\setminus }\hfill & \hfill \hfill \\ \hfill {\text{H}}_3\text{C}\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \text{C}{\text{H}}_3\hfill \end{array}$

   Siedepunkt: 56 °C

   [Verwendung:] Lösungsmittel, Tränengas

   Butanon

   \setlength{\arraycolsep}{0pt} \begin{array}{ccccc} {} & ^{/} & \text{O} & ^{\backslash} & \\ {} & & \vert\vert{} & & \\ {} & & \text{C} & & \\ {} & ^{/} & & ^{\backslash} & \\ {} \text{H}_3\text{C} & & & & \text{C}_2\text{H}_5 \end{array}$\begin{array}{ccccc}\hfill \hfill & \hfill {}^{∕}\hfill & \hfill \text{O}\hfill & \hfill {}^{\setminus }\hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \mid \mid \hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \text{C}\hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill {}^{∕}\hfill & \hfill \hfill & \hfill {}^{\setminus }\hfill & \hfill \hfill \\ \hfill {\text{H}}_3\text{C}\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill {\text{C}}_2{\text{H}}_5\hfill \end{array}$

   b)

   Chemische Eigenschaften

   nicht weiter oxidierbar → Unterscheidung von den Alkanalen

3. Nucleophile Addition an die Carbonylgruppe

   Versuch

   Trichlorethanal + Wasser

   Beobachtung

   Feststoff entsteht.

   Erklärung

   { \setlength{\arraycolsep}{0pt} \begin{array}{ccccccc} {} & & |\overline{\text{Cl}}| & & & & \overline{\text{O}}| \\ {} & & | & & & /\!/ & \\ {} |\overline{\underline{\text{Cl}}} & - & \text{C} & - & \text{C} & & \\ {} & & | & & & \backslash{} & \\ {} & & |\underline{\text{Cl}}| & & & & \text{H} \end{array} } + { \setlength{\arraycolsep}{0pt} \begin{array}{ccccc} {} \text{H} & - & \overline{\underline{\text{O}}} & - & \text{H} \end{array} } \longrightarrow { \setlength{\arraycolsep}{0pt} \begin{array}{ccccccccc} {} & & |\overline{\text{Cl}}| & & & & \overline{\underline{\text{O}}} & - & \text{H} \\ {} & & | & & & / & & & \\ {} |\overline{\underline{\text{Cl}}} & - & \text{C} & - & \text{C} & - & \overline{\underline{\text{O}}} & - & \text{H} \\ {} & & | & & & \backslash{} & & & \\ {} & & |\underline{\text{Cl}}| & & & & \text{H} & & \end{array} } \text{ (Chloralhydrat)}$\begin{array}{ccccccc}\hfill \hfill & \hfill \hfill & \hfill \mid \overline{\text{Cl}}\mid \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \overline{\text{O}}\mid \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \mid \hfill & \hfill \hfill & \hfill \hfill & \hfill ∕∕\hfill & \hfill \hfill \\ \hfill \mid \overline{\underset{¯}{\text{Cl}}}\hfill & \hfill -\hfill & \hfill \text{C}\hfill & \hfill -\hfill & \hfill \text{C}\hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \mid \hfill & \hfill \hfill & \hfill \hfill & \hfill \setminus \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \mid \underset{¯}{\text{Cl}}\mid \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \text{H}\hfill \end{array}+\begin{array}{ccccc}\hfill \text{H}\hfill & \hfill -\hfill & \hfill \overline{\underset{¯}{\text{O}}}\hfill & \hfill -\hfill & \hfill \text{H}\hfill \end{array}\to \begin{array}{ccccccccc}\hfill \hfill & \hfill \hfill & \hfill \mid \overline{\text{Cl}}\mid \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \overline{\underset{¯}{\text{O}}}\hfill & \hfill -\hfill & \hfill \text{H}\hfill \\ \hfill \hfill & \hfill \hfill & \hfill \mid \hfill & \hfill \hfill & \hfill \hfill & \hfill ∕\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill \\ \hfill \mid \overline{\underset{¯}{\text{Cl}}}\hfill & \hfill -\hfill & \hfill \text{C}\hfill & \hfill -\hfill & \hfill \text{C}\hfill & \hfill -\hfill & \hfill \overline{\underset{¯}{\text{O}}}\hfill & \hfill -\hfill & \hfill \text{H}\hfill \\ \hfill \hfill & \hfill \hfill & \hfill \mid \hfill & \hfill \hfill & \hfill \hfill & \hfill \setminus \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \mid \underset{¯}{\text{Cl}}\mid \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \text{H}\hfill & \hfill \hfill & \hfill \hfill \end{array}\text{ (Chloralhydrat)}$

   Die Addition[sbereitschaft] von Wassermolekülen an die Carbonylgruppe ist eine chemische Eigenschaft der Alkanale und Alkanone. Es bilden sich Hydrate.

   → Typische gemeinsame Reaktion der Alkanale und Alkanone

   Starke Polarität der Carbonylgruppe aufgrund der hohen Elektronegativität des Sauerstoffatoms

   { \setlength{\arraycolsep}{0pt} \begin{array}{ccc} {} ^{\delta^+}\text{C} & = & {\text{O}_/^\backslash}^{\delta^-} \end{array} } \leftrightarrow { \setlength{\arraycolsep}{0pt} \begin{array}{ccc} {} ^\oplus\text{C} & - & \overline{\underline{\text{O}}}|^\ominus \end{array} }$\begin{array}{ccc}\hfill {}^{{\delta }^{+}}\text{C}\hfill & \hfill =\hfill & \hfill {{\text{O}}_{∕}^{\setminus }}^{{\delta }^{-}}\hfill \end{array}\leftrightarrow \begin{array}{ccc}\hfill {}^{\oplus }\text{C}\hfill & \hfill -\hfill & \hfill \overline{\underset{¯}{\text{O}}}{\mid }^{\ominus }\hfill \end{array}$

   Allgemein:

   { \setlength{\arraycolsep}{0pt} \begin{array}{cccccc} {} \text{R}_1 & & & & & \\ {} & \backslash{} & & & & \backslash{} \\ {} & & \text{C} & = & \text{O} & \\ {} & / & & & & / \\ {} \text{R}_2 & & & & & \end{array} } + { \setlength{\arraycolsep}{0pt} \begin{array}{cccc} {} | & \text{Nu} & - & \text{H} \end{array} } \longrightarrow { \setlength{\arraycolsep}{0pt} \begin{array}{ccccccc} {} \text{R}_1 & & & & \overline{\underline{\text{O}}} & - & \text{H} \\ {} & \backslash{} & & / & & & \\ {} & & \text{C} & & & & \\ {} & / & & \backslash{} & & & \\ {} \text{R}_2 & & & & \text{Nu} & & \end{array} }$\begin{array}{cccccc}\hfill {\text{R}}_1\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \setminus \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \setminus \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \text{C}\hfill & \hfill =\hfill & \hfill \text{O}\hfill & \hfill \hfill \\ \hfill \hfill & \hfill ∕\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill ∕\hfill \\ \hfill {\text{R}}_2\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill \end{array}+\begin{array}{cccc}\hfill \mid \hfill & \hfill \text{Nu}\hfill & \hfill -\hfill & \hfill \text{H}\hfill \end{array}\to \begin{array}{ccccccc}\hfill {\text{R}}_1\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \overline{\underset{¯}{\text{O}}}\hfill & \hfill -\hfill & \hfill \text{H}\hfill \\ \hfill \hfill & \hfill \setminus \hfill & \hfill \hfill & \hfill ∕\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \text{C}\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill ∕\hfill & \hfill \hfill & \hfill \setminus \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill \\ \hfill {\text{R}}_2\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \text{Nu}\hfill & \hfill \hfill & \hfill \hfill \end{array}$

   Nucleophile: Wasser, Ammoniak, Hydrogenchlorid, Blausäure (HCN), alle Alkanole (\text{R}{-}\overline{\underline{\text{O}}}{-}\text{H}$\text{R}-\overline{\underset{¯}{\text{O}}}-\text{H}$)

   • Säurekatalysierter Mechanismus

     

   • Basenkatalysierter Mechanismus

     

   • Beispiele:

     • Nucleophile Addition von \text{NH}_3${\text{NH}}_3$ an Propanal:

       { \setlength{\arraycolsep}{0pt} \begin{array}{ccccccc} {} & & & & & & \overline{\text{O}}| \\ {} & & & & & /\!/ & \\ {} \text{H}_3\text{C} & - & \text{CH}_2 & - & \text{C} & & \\ {} & & & & & \backslash{} & \\ {} & & & & & & \text{H} \end{array} } + |\text{NH}_3 \longrightarrow { \setlength{\arraycolsep}{0pt} \begin{array}{ccccccccc} {} & & & & & & \overline{\underline{\text{O}}} & - & \text{H} \\ {} & & & & & / & & & \\ {} \text{H}_3\text{C} & - & \text{CH}_2 & - & \text{C} & - & \underline{\text{N}} & \text{H}_2 & \\ {} & & & & & \backslash{} & & & \\ {} & & & & & & \text{H} & & \end{array} }$\begin{array}{ccccccc}\hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \overline{\text{O}}\mid \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill ∕∕\hfill & \hfill \hfill \\ \hfill {\text{H}}_3\text{C}\hfill & \hfill -\hfill & \hfill {\text{CH}}_2\hfill & \hfill -\hfill & \hfill \text{C}\hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \setminus \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \text{H}\hfill \end{array}+\mid {\text{NH}}_3\to \begin{array}{ccccccccc}\hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \overline{\underset{¯}{\text{O}}}\hfill & \hfill -\hfill & \hfill \text{H}\hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill ∕\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill \\ \hfill {\text{H}}_3\text{C}\hfill & \hfill -\hfill & \hfill {\text{CH}}_2\hfill & \hfill -\hfill & \hfill \text{C}\hfill & \hfill -\hfill & \hfill \underset{¯}{\text{N}}\hfill & \hfill {\text{H}}_2\hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \setminus \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \text{H}\hfill & \hfill \hfill & \hfill \hfill \end{array}$

     • Nucleophile Addition von HCN an Propanal:

       { \setlength{\arraycolsep}{0pt} \begin{array}{ccccccc} {} & & & & & & \overline{\text{O}}| \\ {} & & & & & /\!/ & \\ {} \text{H}_3\text{C} & - & \text{CH}_2 & - & \text{C} & & \\ {} & & & & & \backslash{} & \\ {} & & & & & & \text{H} \end{array} } + ^\ominus|\text{C}{\equiv}\text{N}| \longrightarrow { \setlength{\arraycolsep}{0pt} \begin{array}{ccccccccc} {} & & & & & & \overline{\underline{\text{O}}}| & ^\ominus & \\ {} & & & & & / & & & \\ {} \text{H}_3\text{C} & - & \text{CH}_2 & - & \text{C} & - & \text{C} & {\equiv} & \text{N}| \\ {} & & & & & \backslash{} & & & \\ {} & & & & & & \text{H} & & \end{array} }${\begin{array}{ccccccc}\hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \overline{\text{O}}\mid \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill ∕∕\hfill & \hfill \hfill \\ \hfill {\text{H}}_3\text{C}\hfill & \hfill -\hfill & \hfill {\text{CH}}_2\hfill & \hfill -\hfill & \hfill \text{C}\hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \setminus \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \text{H}\hfill \end{array}+}^{\ominus }\mid \text{C}\equiv \text{N}\mid \to \begin{array}{ccccccccc}\hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \overline{\underset{¯}{\text{O}}}\mid \hfill & \hfill {}^{\ominus }\hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill ∕\hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill \\ \hfill {\text{H}}_3\text{C}\hfill & \hfill -\hfill & \hfill {\text{CH}}_2\hfill & \hfill -\hfill & \hfill \text{C}\hfill & \hfill -\hfill & \hfill \text{C}\hfill & \hfill \equiv \hfill & \hfill \text{N}\mid \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \setminus \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill \\ \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \hfill & \hfill \text{H}\hfill & \hfill \hfill & \hfill \hfill \end{array}$

       [zuvor: \text{H}{-}\text{C}{\equiv}\text{N} \longrightarrow \text{H}^+ + ^\ominus|\text{C}{\equiv}\text{N}|$\text{H}-\text{C}\equiv \text{N}\to {\text{H}}^{+}{+}^{\ominus }\mid \text{C}\equiv \text{N}\mid$, da Blausäure ja eine Säure ist]

   • Addition von Alkanalen

     1. Halbacetalbildung

        

     2. Vollacetalbildung

        

   • Weitere Nachweise der Aldehydgruppe

     • \text{Aldehyd} + \text{KMnO}_4 \longrightarrow$\text{Aldehyd}+{\text{KMnO}}_4\to$

       [Aldehyde werden oxidiert, andere Moleküle – z.B. \text{KMnO}_4${\text{KMnO}}_4$ – reduziert.]

     • Aldehyd + SCHIFFsches Reagenz \longrightarrow$\to$ Farbvertiefung

   [Addition von Blausäure zur Kettenverlängerung]

   [Wenn ein C oder ein N eines \text{C}{\equiv}\text{N}$\text{C}\equiv \text{N}$ potentiell angreifen könnte, greift bei uns immer das C an.]

   [Wichtig: Mesomeriestabiliserung der positiven Ladung des C-Atoms (Überklappen eines Elektronenpaars des \overline{\underline{\text{O}}}$\overline{\underset{¯}{\text{O}}}$ zum C → damit trägt das \underline{\text{O}}$\underset{¯}{\text{O}}$ die positive Ladung.]