Ch2 Hydrocarbon Alkyne
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Transcript of Ch2 Hydrocarbon Alkyne
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Prepared by:
Arbanah Muhammad
CH 2_3: UNSAU!A"#H$#!%CA!&%N ' Alkyne(
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). Alkyne(
2. N*menclature %+ Alkyne(
3. Pr*pertie( %+ Alkyne(
,. Synthe(i( %+ Alkyne(-. !eacti*n( %+ Alkyne(
TOPIC COVERED:
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Alkynes
Unsaturated hydrocarbon
Contain carbon carbon triple bonds
Alkynes
General formula
Aliphatic hydrocarbons
!CC!
CnH2n2
Example:
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1. Similar to alkanes and alkenes
Density
Boilin point
!eltin point
In"rease as t#e
n$m%er o& "ar%on
in"rease.
P#ysi"al properties
'. Sol$%ility
( Sol$%le in nonpolar sol)ent
( *ot sol$%le in +ater
,. -o+ density%oilin point and meltin point
/. Properties )ary %ased on "#ain si0e
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-inear
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*amin Alkynes
Similar to Alkenes:
1. Longest chain must contain the triple bond
2. Number of carbons so that the triple bond has the lowestpossible value
. !ndicate the position of the triple bond
". Change ending to - yne
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"/erci(e:
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"/erci(e: #ra0 the (tructure +r*m the +*ll*0in1 UPAC
name:
(propyl '( o"tyne
'(trimet#yl ,( #eptyne
1(%romo#ex(,(yne
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Synt#esis o& alkynes
De#ydro#aloenation
2eminal di#alide
Vi"inal di#alide
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Synt#esis o& alkynes
De#ydro#aloenation o& di#aloalkane
'*a*3'
4
C C
4
3
3
R R5
'*3,
6 RC CR7
6
2eminal di#alide
Sodi$m amidealkyne
Ammonia
'*a4
Sodi$m #alide
6
i. eminal dihalide
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Rea"tion:
R8C C8R7
1ststep
'ndstep
43
*a*3'
4
C C
4
3
3
R R5 6
*3,
*a466
*a*3'6
*3, *a466
R8C C8R7
43
R8C C8R7
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'*a*3'
4
C C
4
3 3
R R5
'*3,
6 RC CR7
6
Vi"inal di#alide
Sodi$m amidealkyne
Ammonia
'*a4
Sodi$m #alide
6
De#ydro#aloenation o& di#aloalkane
ii. Vi"inal di#alide
Synt#esis o&alkynes
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Exer"ise:
Pro)ide a rea"tion to prod$"e o"tyne &rom
t#e rea"tion o&
19 2eminal di#aloalkane
'9 Vi"inal di#aloalkae
it# sodi$m amide
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Rea"tion o& alkynes
1. 3ydroenation'. De#ydro#aloenation
,. 3ydration
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Rea"tion o& alkynes
"atalyst ; Pt Pd *i or R#
"atRC CR7 6 '3'
1. 3ydroenation o& Alkynes
Alkyne
RC CR7"at
3'
"at3'
1ststep
'ndstep
"is alkene
R R5
3 3
CC6
6
Alkane
RC
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=ollo+ !arkoniko)5s r$le
Alkynes are sli#tly less rea"ti)e t#an alkenes
RC
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C3,>C3'9,C C3 3Br
3Br
1ststep
'ndstep
6
6
C3,>C3'9,C C3
3Br
C3,>C3'9,C C3
3Br
Rea"tion o& alkynes
Br
C3,>C3'9,C C3
''(di%romo#exane
3Br
3
Example
1(#exyne3ydroen
%romide'(%romo(1(#exene
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6 'Cl'
Cl
Cl
C3C C3,3C CC3,
,. 3aloenation o& alkynes
Rea"tion o& alkynes
"atalyst
Catalyst; AlCl,? =eCl,
tetra"#loropropane
1(propene
RC
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Rea"tion o& alkynes
RC CR7 3'O6
/. 3ydration o& alkynes
RC3'CR7
O
3'SO/
3SO/
R5 ; alkyl@ etone
R5 ; 3@ Alde#yde
C3,C3'CC3,C3,C3'C C3
O
Example
1(%$tyne '(%$tanone
3'O63'SO/
3SO/
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Exer"ise:
#at is t#e prod$"ts o& t#e rea"tion o&
#exyne +it#:
19 3ydroen
'9 3ydroen &lo$ride
,9 C#loride
/9 ater