Alkynes

1
??????? ?????????
Alkynes Nitriles
Å,
1.203
1.061
180.0
???????????
2
?????? p ???? ???????? s.
CH
H3C-CH3
H2CCH2
HC?CH
sp3-s
sp2-s
sp-s
??? ??????? (R ) ???? ???? ?? Ka ???? ???? ?-Pka
??? ????


sp
sp2
sp3
3
??????????
????? ?? yne.
HC?CH
????
??????
H3C-C?CH
??????
H3C-CH2-C?CH
1-?????
???????
H3C-C?C-CH3
2-?????
????
CaCO3?CO2 CaO
CaO 3C?CO CaC2
CaC2 H2O?HC?CH CaO
4
????. ?????? ?????? ?????
2 CH4 ? HC?CH 3 H2
????????? ?? HX
RCHX-CHXR or RCX2-CH2R
-2HX
R-C?C-R
?????
?? ?-R ?? ?-R, ?? ?????? ???? ?????? ???
RCCHR
?????????? ????? ?????? ???, ???? ?? ??????
??????? ?????.
NaNH2, solid NaOH, alc. KOH
5
??????
R-C?C-H B ? BH R-C?C
CH3-C?C-H BuLi ? CH3CH2CH2CH3
CH3-C?CLi
NaNH2
NH3
PKa(?C-H)25
PKa(NH3)34
R-C?C RX ? R-C?C-R X
6
?????? ?????
??????? ?????? ????? ???????, ?? ???? ???? ???
??????? ????? ??? ??????????? ?? ??????
R-CH2-CH2-R
R-CH2-CX2-R
R-C?C-R
??????????
R-CX2-CX2-R
7
?????
H, -H
R-C?C-R
????
????
???????????? ???-????
???? ?????? ?????? ??????????? (BH3/H2O2) ???
???? ???????? ???????? ?????????
8
Lindlar catalyst
?? "???????" ???????? ?? ???? Pd ?-BaSO4 ???????
?? ?????????? ????? ???????? ?????? ????? ?-???
????.
R-C?C-R
???? ???? ???? ???? ?"? ????? ?? ?????? ???????
R-C?C-R
9
NH3
Li
Li e
R-C?C-R e ?
Li
-NH2
-NH2
NH3
e
NH3
-NH2
NH4Cl LiNH2 ? LiCl 2 NH3
10
????? "???' ??
KAPA K -HN-CH2-CH2-CH2-NH2
11
??????? ?????????
Alkynes Nitriles
??????????
CH3-C?N
??????????
??????????
CH3CH2-C?N
????????????
?????? ????????? ????? ?????????
CH3-C?C-H
CH3-C?N
m0.80 D
m3.30 D
12
????
R-X MC?N ? MX R-C?N
XCl, Br, I
MNa, K
??????
?????? ?????? ?????? ????? ????? ?? ???????, ??
???? ???? ??????
??????????
????
13
?????????
R-C?N H2O ??
????
H
H2O
R-C?N
-H
-H
H
H2O/H
NH4
D