=for timestamp
Do Feb 23 16:49:10 CET 2006

=head3 Carbonylverbindungen

Funktionelle Gruppe:

=for strukturformel
 /O\
  ∥
  C
 / \
1   2
[/] ^{/}
[\] ^{\backslash}
[1] \text{R}_1
[2] \text{R}_2

M<<< \setlength{\arraycolsep}{0pt} \begin{array}{ccccc} {}  & ^{/} & \text{O} & ^{\backslash} &  \\ {}  &  & \vert\vert{} &  &  \\ {}  &  & \text{C} &  &  \\ {}  & ^{/} &  & ^{\backslash} &  \\ {} \text{R}_1 &  &  &  & \text{R}_2  \end{array} >>>

=over

=item 1.

I<Alkanale> (Aldehyde)

=for strukturformel
 /O\
  ∥
  C
 / \
H   2
[/] ^{/}
[\] ^{\backslash}
[2] \text{R}_2

M<<< \setlength{\arraycolsep}{0pt} \begin{array}{ccccc} {}  & ^{/} & \text{O} & ^{\backslash} &  \\ {}  &  & \vert\vert{} &  &  \\ {}  &  & \text{C} &  &  \\ {}  & ^{/} &  & ^{\backslash} &  \\ {} \text{H} &  &  &  & \text{R}_2  \end{array} >>>

=over

=item a)

I<Beispiele>

=for comment
Stukturformeln:
H
 \   \
  C=O
 /   /
H
--
    H H
   / /
H-C-C
   \ `
    H o
[`] \backslash\!\backslash{}
[o] \underline{\text{O}}|
--
       o
 | |  ´
-C-C-C
 | |  \
       H
[´] /\!/
[o] \overline{\text{O}}|
--
[[1]]
  H
 /
C
 `
  o
[`] \backslash\!\backslash{}
[o] \underline{\text{O}}|
[[.]]
\text{C}_5\text{H}_{11}{-}<<1>>
--
   o
  ´
-C
  \
   H
[´] /\!/
[o] \overline{\text{O}}|

=for latex
\begin{scriptsize}

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

=for latex
\end{scriptsize}


=for timestamp
Mi Mär  8 17:54:03 CET 2006

=for comment
Bedeutung und Verwendung in dieser Stunde, nicht letzter.

=item b)

I<Chemische Eigenschaften>

Oxidierbar zu Carbonsäure

=for extstrukturformel
[[1]]
1
 \   \
  C=O
 /   /
H
[1] \text{R}_1
[[2]]
    o
   ´
1-C
   \
    p-H
[1] \text{R}_1
[o] \overline{\text{O}}|
[p] \overline{\underline{\text{O}}}
[´] /\!/
[[.]]
<<1>> + 2\,\text{OH}^- \longrightarrow <<2>> + \text{H}_2\text{O} + 2\,e^-

M<<< { \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^- >>>

→ Nachweis: Silberspiegel- oder Fehlingprobe

=back

=item 2.

I<Ketone> (Alkanone)

=for strukturformel
 /O\
  ∥
  C
 / \
1   2
[/] ^{/}
[\] ^{\backslash}
[1] \text{R}_1
[2] \text{R}_2

M<<< \setlength{\arraycolsep}{0pt} \begin{array}{ccccc} {}  & ^{/} & \text{O} & ^{\backslash} &  \\ {}  &  & \vert\vert{} &  &  \\ {}  &  & \text{C} &  &  \\ {}  & ^{/} &  & ^{\backslash} &  \\ {} \text{R}_1 &  &  &  & \text{R}_2  \end{array} >>>

M<\text{R}_1, \text{R}_2 \neq \text{H}>

=over

=item a)

I<Beispiele>

=over

=item Propanon (Aceton)

=for strukturformel
 /O\
  ∥
  C
 / \
1   2
[/] ^{/}
[\] ^{\backslash}
[1] \text{H}_3\text{C}
[2] \text{C}\text{H}_3

M<<< \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} >>>

Siedepunkt: 56 °C

[Verwendung:] Lösungsmittel, Tränengas

=item Butanon

=for strukturformel
 /O\
  ∥
  C
 / \
1   2
[/] ^{/}
[\] ^{\backslash}
[1] \text{H}_3\text{C}
[2] \text{C}_2\text{H}_5

M<<< \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} >>>

=back

=item b)

I<Chemische Eigenschaften>

nicht weiter oxidierbar → Unterscheidung von den Alkanalen

=back


=for timestamp
Do Mär  9 17:57:07 CET 2006

=item 3.

I<Nucleophile Addition an die Carbonylgruppe>

=over

=item Versuch

Trichlorethanal + Wasser

=item Beobachtung

Feststoff entsteht.

=item Erklärung

=for extstrukturformel
[[1]]
  3   o
  |  ´
1-C-C
  |  \
  2   H
[´] /\!/
[o] \overline{\text{O}}|
[1] |\overline{\underline{\text{Cl}}}
[2] |\underline{\text{Cl}}|
[3] |\overline{\text{Cl}}|
[[3]]
  3   o-H
  |  /
1-C-C-o-H
  |  \
  2   H
[o] \overline{\underline{\text{O}}}
[1] |\overline{\underline{\text{Cl}}}
[2] |\underline{\text{Cl}}|
[3] |\overline{\text{Cl}}|
[[2]]
H-o-H
[o] \overline{\underline{\text{O}}}
[[.]]
<<1>> + <<2>> \longrightarrow <<3>> \text{ (Chloralhydrat)}

M<<< { \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)} >>>

=back

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


=for timestamp
Di Mär 14 17:53:07 CET 2006

=for timestamp
Mi Mär 15 18:40:48 CET 2006

→ Typische gemeinsame Reaktion der Alkanale und Alkanone

Starke Polarität der Carbonylgruppe aufgrund der hohen Elektronegativität des
Sauerstoffatoms

=for extstrukturformel
[[1]]
c=o
[c] ^{\delta^+}\text{C}
[o] {\text{O}_/^\backslash}^{\delta^-}
[[2]]
c-o
[c] ^\oplus\text{C}
[o] \overline{\underline{\text{O}}}|^\ominus
[[.]]
<<1>> \leftrightarrow <<2>>

M<<< { \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} } >>>

Allgemein:

=for extstrukturformel
[[1]]
1
 \   \
  C=O
 /   /
2
[1] \text{R}_1
[2] \text{R}_2
[[2]]
|n-H
[n] \text{Nu}
[[3]]
1   o-H
 \ /
  C
 / \
2   n
[1] \text{R}_1
[2] \text{R}_2
[n] \text{Nu}
[o] \overline{\underline{\text{O}}}
[[.]]
<<1>> + <<2>> \longrightarrow <<3>>

M<<< { \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} } >>>

Nucleophile: Wasser, Ammoniak, Hydrogenchlorid, Blausäure (HCN), alle Alkanole
(M<\text{R}{-}\overline{\underline{\text{O}}}{-}\text{H}>)

=over

=item *

I<Säurekatalysierter Mechanismus>

=helper MyBook::Helper::XFig

#FIG 3.2
Landscape
Center
Metric
A4      
100.00
Single
-2
1200 2
6 4050 854 5011 1470
6 4679 854 5011 1186
1 3 0 1 0 7 50 -1 -1 0.000 1 0.0000 4845 1020 159 159 4845 1020 4950 1140
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4740 1020 4920 1020
-6
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4050 1260 4410 1275
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4275 1035 4230 1470
4 0 0 50 -1 4 18 0.0000 0 210 195 4560 1410 H\001
-6
6 4965 2624 5926 3240
6 5594 2624 5926 2956
1 3 0 1 0 7 50 -1 -1 0.000 1 0.0000 5760 2790 159 159 5760 2790 5865 2910
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5655 2790 5835 2790
-6
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4965 3030 5325 3045
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5190 2805 5145 3240
4 0 0 50 -1 4 18 0.0000 0 210 195 5475 3180 H\001
-6
6 6374 1378 6706 1710
1 3 0 1 0 7 50 -1 -1 0.000 1 0.0000 6540 1544 159 159 6540 1544 6645 1664
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6435 1544 6615 1544
-6
6 2460 675 2835 1875
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 18
	 2700 1815 2685 1785 2715 1755 2745 1740 2775 1740 2805 1725
	 2820 1755 2820 1785 2805 1815 2775 1830 2745 1860 2715 1860
	 2685 1875 2715 1875 2745 1875 2775 1875 2805 1875 2835 1875
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 3
	 2610 930 2655 855 2655 1065
4 0 0 50 -1 4 18 0.0000 0 210 180 2460 885 R\001
4 0 0 50 -1 4 18 0.0000 0 210 180 2490 1800 R\001
-6
6 5535 660 5910 1860
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 18
	 5775 1800 5760 1770 5790 1740 5820 1725 5850 1725 5880 1710
	 5895 1740 5895 1770 5880 1800 5850 1815 5820 1845 5790 1845
	 5760 1860 5790 1860 5820 1860 5850 1860 5880 1860 5910 1860
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 3
	 5685 915 5730 840 5730 1050
4 0 0 50 -1 4 18 0.0000 0 210 180 5535 870 R\001
4 0 0 50 -1 4 18 0.0000 0 210 180 5565 1785 R\001
-6
6 6120 1770 7995 2400
4 0 0 50 -1 4 12 0.0000 0 135 1350 6120 1905 Carboxoniumion\001
4 0 0 50 -1 4 12 0.0000 0 180 1875 6120 2130 [stabil wg. Mesomerie-\001
4 0 0 50 -1 4 12 0.0000 0 180 1140 6120 2355 stabilisierung]\001
-6
6 3000 2430 3375 3630
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 18
	 3240 3570 3225 3540 3255 3510 3285 3495 3315 3495 3345 3480
	 3360 3510 3360 3540 3345 3570 3315 3585 3285 3615 3255 3615
	 3225 3630 3255 3630 3285 3630 3315 3630 3345 3630 3375 3630
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 3
	 3150 2685 3195 2610 3195 2820
4 0 0 50 -1 4 18 0.0000 0 210 180 3000 2640 R\001
4 0 0 50 -1 4 18 0.0000 0 210 180 3030 3555 R\001
-6
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3255 1170 3495 1185
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3255 1245 3480 1260
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3675 1050 3885 1215
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3855 1320 3660 1515
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4830 930 4845 1110
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 2
	0 0 1.00 105.00 150.00
	 5025 1305 5520 1305
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 33
	0 0 1.00 105.00 150.00
	 3345 1095 3345 1065 3375 1035 3375 1005 3405 990 3420 960
	 3450 945 3465 915 3495 900 3525 885 3555 870 3585 855
	 3615 840 3645 840 3675 840 3705 840 3735 840 3765 840
	 3795 840 3825 840 3855 840 3885 840 3915 855 3945 870
	 3960 900 3975 930 3990 960 4005 990 4005 1020 3975 1035
	 3945 1050 3915 1065 3885 1080
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 53
	0 0 1.00 105.00 150.00
	 3810 1485 3810 1515 3810 1545 3810 1575 3825 1605 3855 1635
	 3870 1665 3885 1695 3900 1725 3915 1755 3945 1770 3960 1800
	 3990 1815 4020 1830 4035 1860 4065 1890 4095 1905 4125 1920
	 4155 1935 4185 1935 4215 1950 4245 1950 4275 1950 4305 1950
	 4335 1950 4365 1950 4395 1950 4425 1950 4455 1950 4485 1950
	 4515 1950 4545 1950 4575 1950 4605 1950 4635 1935 4665 1905
	 4695 1890 4710 1860 4725 1830 4740 1800 4755 1770 4785 1740
	 4800 1710 4815 1680 4830 1650 4830 1620 4845 1590 4845 1560
	 4845 1530 4845 1500 4815 1485 4785 1470 4770 1440
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 7455 1260 7680 1275
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 7575 1110 7560 1410
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 2
	0 0 1.00 105.00 150.00
	 9405 1170 9720 1170
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 2
	0 0 1.00 105.00 150.00
	 7755 1845 9345 1830
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 2
	0 0 1.00 105.00 150.00
	 2370 2970 2850 2955
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3840 2865 4065 2610
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4410 2445 4620 2460
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3780 3135 4065 3375
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 8100 1200 8370 1215
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 8760 1200 9045 1215
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 8475 1065 8655 1065
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 8445 1395 8685 1365
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4335 3555 4560 3555
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4065 3705 4275 3720
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4140 3360 4320 3420
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6705 600 6915 615
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6705 960 6915 915
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4140 2580 4365 2610
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4140 2295 4365 2280
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5760 2685 5760 2880
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6405 1200 6630 945
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6975 780 7185 795
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6510 1440 6525 1635
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 2700 915 2925 1125
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 2970 1395 2745 1560
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5865 990 6090 1200
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6135 1470 5910 1635
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 59
	 8040 720 8010 720 7995 750 7980 780 7965 810 7980 840
	 8010 840 8025 870 7995 900 8025 915 7995 930 7965 945
	 7995 960 8025 960 8055 960 8025 975 7995 990 7980 1020
	 8010 1020 8040 1020 8025 1050 7995 1050 7980 1080 8010 1080
	 8040 1080 8040 1110 8040 1140 8010 1155 7995 1185 7965 1185
	 7995 1200 8025 1200 8055 1200 8025 1200 7995 1215 7980 1245
	 8010 1245 8040 1260 8055 1290 8040 1320 8070 1335 8040 1350
	 8025 1380 7995 1395 7995 1425 8025 1440 7995 1455 8025 1470
	 8040 1500 8025 1530 8025 1560 8055 1560 8040 1590 8070 1590
	 8100 1605 8070 1620 8055 1650 8055 1680 8025 1680
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3300 2655 3525 2865
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3570 3135 3345 3300
4 0 0 50 -1 4 18 0.0000 0 210 225 3555 1380 O\001
4 0 0 50 -1 4 18 0.0000 0 210 225 4125 2550 O\001
4 0 0 50 -1 4 18 0.0000 0 210 195 4665 2565 H\001
4 0 0 50 -1 4 18 0.0000 0 210 225 4065 3660 O\001
4 0 0 50 -1 4 18 0.0000 0 210 225 8460 1320 O\001
4 0 0 50 -1 4 18 0.0000 0 210 195 9105 1320 H\001
4 0 0 50 -1 4 18 0.0000 0 210 225 6690 885 O\001
4 0 0 50 -1 4 18 0.0000 0 210 195 7230 900 H\001
4 0 0 50 -1 4 18 0.0000 0 210 210 2970 1350 C\001
4 0 0 50 -1 4 18 0.0000 0 210 210 6135 1425 C\001
4 0 0 50 -1 4 18 0.0000 0 210 195 7770 1305 H\001
4 0 0 50 -1 4 18 0.0000 0 210 210 3570 3090 C\001
4 0 0 50 -1 4 18 0.0000 0 210 195 4635 3645 H\001

=hend

=item *

I<Basenkatalysierter Mechanismus>

=helper MyBook::Helper::XFig

#FIG 3.2
Landscape
Center
Metric
A4      
100.00
Single
-2
1200 2
6 5535 660 5910 1860
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 18
	 5775 1800 5760 1770 5790 1740 5820 1725 5850 1725 5880 1710
	 5895 1740 5895 1770 5880 1800 5850 1815 5820 1845 5790 1845
	 5760 1860 5790 1860 5820 1860 5850 1860 5880 1860 5910 1860
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 3
	 5685 915 5730 840 5730 1050
4 0 0 50 -1 4 18 0.0000 0 210 180 5535 870 R\001
4 0 0 50 -1 4 18 0.0000 0 210 180 5565 1785 R\001
-6
6 3000 2430 3375 3630
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 18
	 3240 3570 3225 3540 3255 3510 3285 3495 3315 3495 3345 3480
	 3360 3510 3360 3540 3345 3570 3315 3585 3285 3615 3255 3615
	 3225 3630 3255 3630 3285 3630 3315 3630 3345 3630 3375 3630
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 3
	 3150 2685 3195 2610 3195 2820
4 0 0 50 -1 4 18 0.0000 0 210 180 3000 2640 R\001
4 0 0 50 -1 4 18 0.0000 0 210 180 3030 3555 R\001
-6
6 4873 885 5205 1217
1 3 0 1 0 7 50 -1 -1 0.000 1 0.0000 5039 1051 159 159 5039 1051 5144 1171
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4934 1051 5114 1051
-6
6 8445 1065 8685 1395
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 8475 1065 8655 1065
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 8445 1395 8685 1365
4 0 0 50 -1 4 18 0.0000 0 210 225 8460 1320 O\001
-6
6 7003 300 7335 632
1 3 0 1 0 7 50 -1 -1 0.000 1 0.0000 7169 466 159 159 7169 466 7274 586
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 7064 466 7244 466
-6
6 6616 1650 7065 1980
6 6616 1650 6856 1980
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6646 1650 6826 1650
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6616 1980 6856 1950
4 0 0 50 -1 4 18 0.0000 0 210 225 6631 1905 O\001
-6
4 0 0 50 -1 4 18 0.0000 0 210 195 6870 1921 H\001
-6
6 3960 1050 4949 1530
6 3960 1050 4320 1485
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3960 1275 4320 1290
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4185 1050 4140 1485
-6
6 4500 1170 4949 1500
6 4500 1170 4740 1500
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4530 1170 4710 1170
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4500 1500 4740 1470
4 0 0 50 -1 4 18 0.0000 0 210 225 4515 1425 O\001
-6
4 0 0 50 -1 4 18 0.0000 0 210 195 4754 1441 H\001
-6
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4440 1185 4440 1530
-6
6 4950 2790 5939 3270
6 4950 2790 5310 3225
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4950 3015 5310 3030
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5175 2790 5130 3225
-6
6 5490 2910 5939 3240
6 5490 2910 5730 3240
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5520 2910 5700 2910
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5490 3240 5730 3210
4 0 0 50 -1 4 18 0.0000 0 210 225 5505 3165 O\001
-6
4 0 0 50 -1 4 18 0.0000 0 210 195 5744 3181 H\001
-6
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5430 2925 5430 3270
-6
6 2265 675 3869 1875
6 2265 675 2640 1875
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 18
	 2505 1815 2490 1785 2520 1755 2550 1740 2580 1740 2610 1725
	 2625 1755 2625 1785 2610 1815 2580 1830 2550 1860 2520 1860
	 2490 1875 2520 1875 2550 1875 2580 1875 2610 1875 2640 1875
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 3
	 2415 930 2460 855 2460 1065
4 0 0 50 -1 4 18 0.0000 0 210 180 2265 885 R\001
4 0 0 50 -1 4 18 0.0000 0 210 180 2295 1800 R\001
-6
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3060 1170 3300 1185
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3060 1245 3285 1260
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3480 1050 3690 1215
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3660 1320 3465 1515
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 33
	0 0 1.00 105.00 150.00
	 3150 1095 3150 1065 3180 1035 3180 1005 3210 990 3225 960
	 3255 945 3270 915 3300 900 3330 885 3360 870 3390 855
	 3420 840 3450 840 3480 840 3510 840 3540 840 3570 840
	 3600 840 3630 840 3660 840 3690 840 3720 855 3750 870
	 3765 900 3780 930 3795 960 3810 990 3810 1020 3780 1035
	 3750 1050 3720 1065 3690 1080
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 2505 915 2730 1125
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 2775 1395 2550 1560
4 0 0 50 -1 4 18 0.0000 0 210 225 3360 1380 O\001
4 0 0 50 -1 4 18 0.0000 0 210 210 2775 1350 C\001
-6
6 5893 2670 6225 3002
1 3 0 1 0 7 50 -1 -1 0.000 1 0.0000 6059 2836 159 159 6059 2836 6164 2956
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5954 2836 6134 2836
-6
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 2
	0 0 1.00 105.00 150.00
	 5025 1305 5520 1305
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 7455 1260 7680 1275
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 7575 1110 7560 1410
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 2
	0 0 1.00 105.00 150.00
	 9405 1170 9720 1170
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 2
	0 0 1.00 105.00 150.00
	 7755 1845 9345 1830
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 2
	0 0 1.00 105.00 150.00
	 2370 2970 2850 2955
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3840 2865 4065 2610
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4410 2445 4620 2460
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3780 3135 4065 3375
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 8100 1200 8370 1215
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 8760 1200 9045 1215
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4335 3555 4560 3555
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4065 3705 4275 3720
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4140 3360 4320 3420
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6705 600 6915 615
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6705 960 6915 915
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4140 2580 4365 2610
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4140 2295 4365 2280
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6405 1200 6630 945
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5865 990 6090 1200
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6135 1470 5910 1635
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 59
	 8040 720 8010 720 7995 750 7980 780 7965 810 7980 840
	 8010 840 8025 870 7995 900 8025 915 7995 930 7965 945
	 7995 960 8025 960 8055 960 8025 975 7995 990 7980 1020
	 8010 1020 8040 1020 8025 1050 7995 1050 7980 1080 8010 1080
	 8040 1080 8040 1110 8040 1140 8010 1155 7995 1185 7965 1185
	 7995 1200 8025 1200 8055 1200 8025 1200 7995 1215 7980 1245
	 8010 1245 8040 1260 8055 1290 8040 1320 8070 1335 8040 1350
	 8025 1380 7995 1395 7995 1425 8025 1440 7995 1455 8025 1470
	 8040 1500 8025 1530 8025 1560 8055 1560 8040 1590 8070 1590
	 8100 1605 8070 1620 8055 1650 8055 1680 8025 1680
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3300 2655 3525 2865
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3570 3135 3345 3300
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 7005 615 7035 915
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6345 1425 6555 1635
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 31
	0 0 1.00 105.00 150.00
	 7110 885 7095 855 7125 840 7155 825 7185 810 7200 780
	 7230 780 7260 780 7290 765 7320 765 7350 750 7380 750
	 7410 750 7440 750 7470 750 7500 750 7530 750 7560 750
	 7590 750 7620 750 7650 750 7680 765 7710 780 7725 810
	 7755 825 7770 855 7785 885 7800 915 7815 945 7830 975
	 7845 1005
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 54
	0 0 1.00 105.00 150.00
	 4380 1605 4350 1620 4335 1650 4335 1680 4320 1710 4290 1725
	 4275 1755 4245 1770 4215 1800 4185 1815 4155 1830 4125 1845
	 4095 1845 4065 1860 4035 1875 4005 1890 3975 1905 3945 1905
	 3915 1905 3885 1905 3855 1920 3825 1920 3795 1920 3765 1920
	 3735 1920 3705 1920 3675 1920 3645 1920 3615 1920 3585 1920
	 3555 1905 3510 1905 3465 1905 3435 1890 3405 1875 3375 1860
	 3345 1845 3315 1830 3285 1800 3255 1785 3225 1770 3195 1740
	 3165 1725 3150 1695 3135 1665 3105 1650 3075 1635 3060 1605
	 3030 1590 3000 1560 2970 1530 2940 1515 2925 1485 2910 1455
4 0 0 50 -1 4 18 0.0000 0 210 225 4125 2550 O\001
4 0 0 50 -1 4 18 0.0000 0 210 195 4665 2565 H\001
4 0 0 50 -1 4 18 0.0000 0 210 225 4065 3660 O\001
4 0 0 50 -1 4 18 0.0000 0 210 195 9105 1320 H\001
4 0 0 50 -1 4 18 0.0000 0 210 225 6690 885 O\001
4 0 0 50 -1 4 18 0.0000 0 210 210 6135 1425 C\001
4 0 0 50 -1 4 18 0.0000 0 210 195 7770 1305 H\001
4 0 0 50 -1 4 18 0.0000 0 210 210 3570 3090 C\001
4 0 0 50 -1 4 18 0.0000 0 210 195 4635 3645 H\001

=hend

=for timestamp
Mi Mär 15 20:48:31 CET 2006

=item *

Beispiele:

=over

=item *

Nucleophile Addition von M<\text{NH}_3> an Propanal:

=for extstrukturformel
[[1]]
      o
     ´
1-2-C
     \
      H
[1] \text{H}_3\text{C}
[2] \text{CH}_2
[´] /\!/
[o] \overline{\text{O}}|
[[2]]
      o-H
     /
1-2-C-nh
     \
      H
[1] \text{H}_3\text{C}
[2] \text{CH}_2
[o] \overline{\underline{\text{O}}}
[n] \underline{\text{N}}
[h] \text{H}_2
[[.]]
<<1>> + |\text{NH}_3 \longrightarrow <<2>>

M<<< { \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} } >>>

=item *

Nucleophile Addition von HCN an Propanal:

=for extstrukturformel
[[1]]
      o
     ´
1-2-C
     \
      H
[1] \text{H}_3\text{C}
[2] \text{CH}_2
[´] /\!/
[o] \overline{\text{O}}|
[[2]]
      o*
     /
1-2-C-C≡n
     \
      H
[1] \text{H}_3\text{C}
[2] \text{CH}_2
[o] \overline{\underline{\text{O}}}|
[*] ^\ominus
[n] \text{N}|
[[.]]
<<1>> + ^\ominus|\text{C}{\equiv}\text{N}| \longrightarrow <<2>>

M<<< { \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} } >>>

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

=back

=for timestamp
Di Mär 14 17:53:07 CET 2006

=item *

I<Addition von Alkanalen>

=over

=item 1.

Halbacetalbildung

=helper MyBook::Helper::XFig

#FIG 3.2
Landscape
Center
Metric
A4      
100.00
Single
-2
1200 2
6 2460 675 3180 1800
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 2700 915 2925 1125
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 2970 1395 2745 1560
4 0 0 50 -1 4 18 0.0000 0 210 180 2460 885 R\001
4 0 0 50 -1 4 18 0.0000 0 210 195 2490 1800 H\001
4 0 0 50 -1 4 18 0.0000 0 210 210 2970 1350 C\001
-6
6 3060 2415 3780 3540
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3300 2655 3525 2865
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3570 3135 3345 3300
4 0 0 50 -1 4 18 0.0000 0 210 180 3060 2625 R\001
4 0 0 50 -1 4 18 0.0000 0 210 195 3090 3540 H\001
4 0 0 50 -1 4 18 0.0000 0 210 210 3570 3090 C\001
-6
6 7770 1095 8040 1425
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 3
	 7995 1290 8040 1215 8040 1425
4 0 0 50 -1 4 18 0.0000 0 210 180 7770 1305 R\001
-6
6 4590 3405 4860 3735
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 3
	 4815 3600 4860 3525 4860 3735
4 0 0 50 -1 4 18 0.0000 0 210 180 4590 3615 R\001
-6
6 4050 854 5011 1470
6 4679 854 5011 1186
1 3 0 1 0 7 50 -1 -1 0.000 1 0.0000 4845 1020 159 159 4845 1020 4950 1140
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4740 1020 4920 1020
-6
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4050 1260 4410 1275
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4275 1035 4230 1470
4 0 0 50 -1 4 18 0.0000 0 210 195 4560 1410 H\001
-6
6 4965 2624 5926 3240
6 5594 2624 5926 2956
1 3 0 1 0 7 50 -1 -1 0.000 1 0.0000 5760 2790 159 159 5760 2790 5865 2910
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5655 2790 5835 2790
-6
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4965 3030 5325 3045
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5190 2805 5145 3240
4 0 0 50 -1 4 18 0.0000 0 210 195 5475 3180 H\001
-6
6 5625 750 6345 1875
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5865 990 6090 1200
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6135 1470 5910 1635
4 0 0 50 -1 4 18 0.0000 0 210 180 5625 960 R\001
4 0 0 50 -1 4 18 0.0000 0 210 195 5655 1875 H\001
4 0 0 50 -1 4 18 0.0000 0 210 210 6135 1425 C\001
-6
6 6374 1378 6706 1710
1 3 0 1 0 7 50 -1 -1 0.000 1 0.0000 6540 1544 159 159 6540 1544 6645 1664
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6435 1544 6615 1544
-6
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3255 1170 3495 1185
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3255 1245 3480 1260
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3675 1050 3885 1215
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3855 1320 3660 1515
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4830 930 4845 1110
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 2
	0 0 1.00 105.00 150.00
	 5025 1305 5520 1305
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 33
	0 0 1.00 105.00 150.00
	 3345 1095 3345 1065 3375 1035 3375 1005 3405 990 3420 960
	 3450 945 3465 915 3495 900 3525 885 3555 870 3585 855
	 3615 840 3645 840 3675 840 3705 840 3735 840 3765 840
	 3795 840 3825 840 3855 840 3885 840 3915 855 3945 870
	 3960 900 3975 930 3990 960 4005 990 4005 1020 3975 1035
	 3945 1050 3915 1065 3885 1080
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 53
	0 0 1.00 105.00 150.00
	 3810 1485 3810 1515 3810 1545 3810 1575 3825 1605 3855 1635
	 3870 1665 3885 1695 3900 1725 3915 1755 3945 1770 3960 1800
	 3990 1815 4020 1830 4035 1860 4065 1890 4095 1905 4125 1920
	 4155 1935 4185 1935 4215 1950 4245 1950 4275 1950 4305 1950
	 4335 1950 4365 1950 4395 1950 4425 1950 4455 1950 4485 1950
	 4515 1950 4545 1950 4575 1950 4605 1950 4635 1935 4665 1905
	 4695 1890 4710 1860 4725 1830 4740 1800 4755 1770 4785 1740
	 4800 1710 4815 1680 4830 1650 4830 1620 4845 1590 4845 1560
	 4845 1530 4845 1500 4815 1485 4785 1470 4770 1440
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 7455 1260 7680 1275
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 7575 1110 7560 1410
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 59
	 9090 675 9060 675 9045 705 9030 735 9015 765 9030 795
	 9060 795 9075 825 9045 855 9075 870 9045 885 9015 900
	 9045 915 9075 915 9105 915 9075 930 9045 945 9030 975
	 9060 975 9090 975 9075 1005 9045 1005 9030 1035 9060 1035
	 9090 1035 9090 1065 9090 1095 9060 1110 9045 1140 9015 1140
	 9045 1155 9075 1155 9105 1155 9075 1155 9045 1170 9030 1200
	 9060 1200 9090 1215 9105 1245 9090 1275 9120 1290 9090 1305
	 9075 1335 9045 1350 9045 1380 9075 1395 9045 1410 9075 1425
	 9090 1455 9075 1485 9075 1515 9105 1515 9090 1545 9120 1545
	 9150 1560 9120 1575 9105 1605 9105 1635 9075 1635
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 2
	0 0 1.00 105.00 150.00
	 9405 1170 9720 1170
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 2
	0 0 1.00 105.00 150.00
	 7755 1845 9345 1830
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 2
	0 0 1.00 105.00 150.00
	 2370 2970 2850 2955
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3840 2865 4065 2610
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4410 2445 4620 2460
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3780 3135 4065 3375
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 8100 1200 8370 1215
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 8760 1200 9045 1215
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 8475 1065 8655 1065
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 8445 1395 8685 1365
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4335 3555 4560 3555
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4065 3705 4275 3720
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4140 3360 4320 3420
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6705 600 6915 615
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6705 960 6915 915
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4140 2580 4365 2610
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4140 2295 4365 2280
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5760 2685 5760 2880
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6405 1200 6630 945
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6975 780 7185 795
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6510 1440 6525 1635
4 0 0 50 -1 4 18 0.0000 0 210 225 3555 1380 O\001
4 0 0 50 -1 4 18 0.0000 0 210 225 4125 2550 O\001
4 0 0 50 -1 4 18 0.0000 0 210 195 4665 2565 H\001
4 0 0 50 -1 4 18 0.0000 0 210 225 4065 3660 O\001
4 0 0 50 -1 4 18 0.0000 0 210 225 8460 1320 O\001
4 0 0 50 -1 4 18 0.0000 0 210 195 9105 1320 H\001
4 0 0 50 -1 4 18 0.0000 0 210 225 6690 885 O\001
4 0 0 50 -1 4 18 0.0000 0 210 195 7230 900 H\001

=hend

=item 2.

Vollacetalbildung

=helper MyBook::Helper::XFig

#FIG 3.2
Landscape
Center
Metric
A4      
100.00
Single
-2
1200 2
6 8400 3375 8670 3705
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 3
	 8625 3570 8670 3495 8670 3705
4 0 0 50 -1 4 18 0.0000 0 210 180 8400 3585 R\001
-6
6 6870 2385 7590 3510
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 7110 2625 7335 2835
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 7380 3105 7155 3270
4 0 0 50 -1 4 18 0.0000 0 210 180 6870 2595 R\001
4 0 0 50 -1 4 18 0.0000 0 210 195 6900 3510 H\001
4 0 0 50 -1 4 18 0.0000 0 210 210 7380 3060 C\001
-6
6 8730 2760 9090 3060
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 8730 2895 9090 2895
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 8940 2760 8910 3060
-6
6 3060 2280 4860 3735
6 3060 2415 3780 3540
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3300 2655 3525 2865
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3570 3135 3345 3300
4 0 0 50 -1 4 18 0.0000 0 210 180 3060 2625 R\001
4 0 0 50 -1 4 18 0.0000 0 210 195 3090 3540 H\001
4 0 0 50 -1 4 18 0.0000 0 210 210 3570 3090 C\001
-6
6 4590 3405 4860 3735
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 3
	 4815 3600 4860 3525 4860 3735
4 0 0 50 -1 4 18 0.0000 0 210 180 4590 3615 R\001
-6
6 4125 2280 4620 2610
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4410 2445 4620 2460
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4140 2580 4365 2610
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4140 2295 4365 2280
4 0 0 50 -1 4 18 0.0000 0 210 225 4125 2550 O\001
-6
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3840 2865 4065 2610
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3780 3135 4065 3375
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4335 3555 4560 3555
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4065 3705 4275 3720
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4140 3360 4320 3420
4 0 0 50 -1 4 18 0.0000 0 210 195 4665 2565 H\001
4 0 0 50 -1 4 18 0.0000 0 210 225 4065 3660 O\001
-6
6 7623 2598 7905 2880
1 3 0 1 0 7 50 -1 -1 0.000 1 0.0000 7764 2739 134 134 7764 2739 7884 2799
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 7689 2724 7854 2739
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 7764 2634 7779 2829
-6
6 5010 2553 5925 3120
6 5643 2553 5925 2835
1 3 0 1 0 7 50 -1 -1 0.000 1 0.0000 5784 2694 134 134 5784 2694 5904 2754
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5709 2679 5874 2694
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5784 2589 5799 2784
-6
6 5010 2820 5370 3120
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5010 2955 5370 2955
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5220 2820 5190 3120
-6
4 0 0 50 -1 4 18 0.0000 0 210 195 5490 3060 H\001
-6
6 2790 4095 7410 5550
6 3405 4410 3900 4740
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3690 4575 3900 4590
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3420 4710 3645 4740
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 3420 4425 3645 4410
4 0 0 50 -1 4 18 0.0000 0 210 225 3405 4680 O\001
-6
6 4455 4230 5175 5355
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4695 4470 4920 4680
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 4965 4950 4740 5115
4 0 0 50 -1 4 18 0.0000 0 210 180 4455 4440 R\001
4 0 0 50 -1 4 18 0.0000 0 210 195 4485 5355 H\001
4 0 0 50 -1 4 18 0.0000 0 210 210 4965 4905 C\001
-6
6 5985 5220 6255 5550
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 3
	 6210 5415 6255 5340 6255 5550
4 0 0 50 -1 4 18 0.0000 0 210 180 5985 5430 R\001
-6
6 5520 4095 6015 4425
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5805 4260 6015 4275
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5535 4395 5760 4425
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5535 4110 5760 4095
4 0 0 50 -1 4 18 0.0000 0 210 225 5520 4365 O\001
-6
6 2850 4455 3165 4800
6 3030 4620 3165 4800
2 1 0 1 0 7 50 -1 -1 3.000 0 0 -1 0 0 16
	 3030 4665 3045 4635 3075 4620 3105 4620 3135 4620 3150 4650
	 3150 4680 3150 4710 3120 4725 3090 4740 3075 4770 3045 4785
	 3075 4800 3105 4800 3135 4800 3165 4800
-6
4 0 0 50 -1 4 18 0.0000 0 210 180 2850 4665 R\001
-6
6 6060 4095 6375 4440
6 6240 4260 6375 4440
2 1 0 1 0 7 50 -1 -1 3.000 0 0 -1 0 0 16
	 6240 4305 6255 4275 6285 4260 6315 4260 6345 4260 6360 4290
	 6360 4320 6360 4350 6330 4365 6300 4380 6285 4410 6255 4425
	 6285 4440 6315 4440 6345 4440 6375 4440
-6
4 0 0 50 -1 4 18 0.0000 0 210 180 6060 4305 R\001
-6
6 6495 4383 7410 4950
6 7128 4383 7410 4665
1 3 0 1 0 7 50 -1 -1 0.000 1 0.0000 7269 4524 134 134 7269 4524 7389 4584
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 7194 4509 7359 4524
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 7269 4419 7284 4614
-6
6 6495 4650 6855 4950
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6495 4785 6855 4785
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 6705 4650 6675 4950
-6
4 0 0 50 -1 4 18 0.0000 0 210 195 6975 4890 H\001
-6
2 1 0 1 0 7 50 -1 -1 3.000 0 0 -1 1 0 2
	0 0 1.00 105.00 150.00
	 2790 4845 4350 4845
2 1 0 1 0 7 50 -1 -1 3.000 0 0 -1 0 0 2
	 3195 4590 3360 4590
2 1 0 1 0 7 50 -1 -1 3.000 0 0 -1 0 0 46
	 3990 4215 3960 4230 3945 4260 3975 4275 4005 4275 3975 4290
	 4020 4305 4050 4320 4005 4335 3975 4335 3945 4335 3975 4350
	 4005 4350 3975 4365 3990 4395 3990 4425 3960 4440 3990 4455
	 3960 4485 3930 4485 3930 4515 3960 4530 3990 4530 3990 4560
	 3960 4575 3930 4575 3960 4590 3990 4605 4020 4605 3990 4635
	 3960 4635 3930 4650 3960 4665 3990 4665 3975 4695 3960 4725
	 3990 4725 3990 4755 3960 4785 3945 4815 3975 4830 3975 4860
	 3975 4890 3975 4920 3975 4950 3960 4980
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5235 4680 5460 4425
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5175 4950 5460 5190
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5730 5370 5955 5370
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5460 5520 5670 5535
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 5535 5175 5715 5235
4 0 0 50 -1 4 18 0.0000 0 210 195 3975 4695 H\001
4 0 0 50 -1 4 18 0.0000 0 210 225 5460 5475 O\001
-6
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 1 0 2
	0 0 1.00 105.00 150.00
	 5985 2940 6810 2940
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 7590 3105 7875 3345
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 8145 3525 8370 3525
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 7875 3675 8085 3690
2 1 0 1 0 7 50 -1 -1 0.000 0 0 -1 0 0 2
	 7950 3330 8130 3390
2 1 2 1 0 7 50 -1 -1 3.000 0 0 -1 0 0 189
	 3765 2865 3765 2895 3795 2925 3810 2955 3840 2970 3870 2985
	 3900 2985 3930 2985 3960 2970 3990 2970 4020 2970 4050 2970
	 4080 2955 4110 2955 4140 2955 4170 2955 4200 2955 4230 2955
	 4260 2955 4305 2955 4335 2955 4365 2955 4395 2955 4425 2955
	 4455 2940 4485 2940 4515 2940 4545 2955 4575 2955 4605 2970
	 4635 2985 4665 3000 4695 3015 4725 3045 4755 3075 4785 3075
	 4815 3105 4845 3120 4875 3135 4905 3135 4935 3150 4965 3165
	 4995 3180 5025 3180 5055 3180 5085 3180 5115 3195 5145 3195
	 5175 3195 5205 3210 5235 3210 5265 3210 5295 3225 5325 3225
	 5355 3225 5385 3225 5415 3225 5445 3225 5475 3225 5505 3225
	 5535 3225 5565 3225 5595 3210 5610 3180 5625 3150 5655 3150
	 5685 3135 5715 3105 5745 3090 5775 3075 5805 3045 5835 3015
	 5865 3000 5880 2970 5910 2940 5925 2910 5955 2895 5970 2865
	 5985 2835 6000 2805 6000 2775 6015 2745 6030 2715 6030 2685
	 6045 2655 6045 2625 6060 2595 6060 2565 6060 2535 6045 2505
	 6015 2490 6000 2460 5970 2445 5940 2430 5895 2415 5865 2415
	 5835 2400 5805 2400 5775 2400 5745 2415 5715 2415 5685 2430
	 5655 2430 5625 2445 5595 2475 5565 2475 5535 2505 5505 2520
	 5475 2535 5445 2535 5415 2550 5385 2550 5355 2550 5325 2565
	 5295 2565 5265 2565 5235 2565 5205 2565 5175 2565 5145 2565
	 5115 2565 5085 2550 5085 2520 5070 2490 5070 2460 5040 2430
	 5025 2400 4995 2385 4980 2355 4950 2340 4920 2310 4875 2280
	 4845 2265 4815 2250 4785 2235 4755 2220 4725 2205 4695 2190
	 4665 2190 4635 2175 4605 2175 4575 2160 4545 2160 4515 2145
	 4485 2145 4455 2130 4425 2130 4395 2115 4365 2115 4335 2100
	 4305 2100 4275 2100 4245 2100 4215 2100 4185 2100 4155 2115
	 4125 2115 4095 2115 4065 2130 4035 2130 4005 2145 3975 2160
	 3945 2160 3930 2190 3900 2205 3885 2235 3855 2250 3840 2280
	 3810 2295 3795 2325 3780 2355 3765 2385 3735 2415 3735 2445
	 3720 2475 3720 2505 3705 2535 3705 2565 3690 2595 3690 2625
	 3690 2655 3690 2685 3705 2715 3705 2745 3720 2775 3735 2805
	 3750 2835 3765 2865 3765 2895
2 1 0 1 0 7 50 -1 -1 3.000 0 0 -1 0 0 16
	 9375 3045 9390 3015 9420 3000 9450 3000 9480 3000 9495 3030
	 9495 3060 9495 3090 9465 3105 9435 3120 9420 3150 9390 3165
	 9420 3180 9450 3180 9480 3180 9510 3180
2 1 2 1 0 7 50 -1 -1 3.000 0 0 -1 1 0 122
	0 0 1.00 105.00 150.00
	 4980 2220 4995 2190 5025 2160 5055 2130 5085 2115 5115 2085
	 5145 2070 5175 2055 5205 2025 5250 2010 5295 1995 5325 1980
	 5370 1965 5400 1950 5430 1935 5460 1920 5490 1920 5520 1905
	 5550 1890 5580 1875 5610 1860 5640 1830 5670 1830 5700 1830
	 5730 1815 5760 1815 5790 1815 5835 1800 5865 1800 5895 1800
	 5925 1785 5970 1785 6000 1785 6030 1785 6060 1770 6105 1770
	 6135 1755 6165 1755 6195 1755 6225 1740 6255 1740 6300 1740
	 6330 1725 6360 1725 6405 1725 6435 1710 6465 1710 6510 1695
	 6540 1695 6585 1695 6630 1695 6660 1695 6690 1695 6720 1695
	 6750 1695 6840 1725 6870 1725 6915 1725 6945 1725 7035 1755
	 7080 1755 7125 1755 7155 1755 7200 1755 7230 1770 7260 1770
	 7290 1785 7320 1785 7350 1800 7380 1815 7410 1815 7440 1815
	 7530 1845 7560 1845 7590 1860 7620 1860 7665 1860 7695 1875
	 7725 1875 7770 1890 7815 1905 7845 1920 7875 1920 7935 1980
	 7965 1980 7995 1995 8100 2040 8145 2055 8175 2055 8205 2070
	 8250 2070 8280 2085 8310 2085 8340 2100 8370 2115 8400 2115
	 8445 2145 8490 2160 8535 2175 8565 2175 8595 2190 8625 2205
	 8655 2205 8670 2235 8700 2235 8745 2265 8790 2295 8820 2310
	 8865 2340 8895 2370 8925 2385 8955 2415 8985 2415 9015 2430
	 9045 2445 9075 2460 9105 2460 9150 2475 9180 2490 9210 2520
	 9240 2535 9270 2550
2 1 0 1 0 7 50 -1 -1 3.000 0 0 -1 1 0 2
	0 0 1.00 105.00 150.00
	 9825 2880 10350 2880
4 0 0 50 -1 4 18 0.0000 0 210 225 7875 3630 O\001
4 0 0 50 -1 4 18 0.0000 0 210 195 9150 3015 H\001
4 0 0 50 -1 4 18 0.0000 0 210 225 9495 3000 O\001

=hend


=back

=item *

I<Weitere Nachweise der Aldehydgruppe>

=over

=item *

M<\text{Aldehyd} + \text{KMnO}_4 \longrightarrow>

[Aldehyde werden oxidiert, andere Moleküle -- z.B. M<\text{KMnO}_4> --
reduziert.]

=for timestamp
Mi Mär 15 18:40:48 CET 2006

=item *

Aldehyd + SCHIFFsches Reagenz M<\longrightarrow> Farbvertiefung

=back

=back

=for timestamp
Di Mär 14 17:53:07 CET 2006

[Addition von Blausäure zur Kettenverlängerung]


=for timestamp
Mi Mär 15 18:40:48 CET 2006

[Wenn ein C oder ein N eines M<\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 M<\overline{\underline{\text{O}}}> zum C → damit
trägt das M<\underline{\text{O}}> die positive Ladung.]

=back