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Alkuna

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Alkuna adalah hidrokarbon tak jenuh yang memiliki ikatan rangkap tiga. Secara umum,
rumus kimianya CnH2n-2. Salah satunya adalah etuna yang disebut juga sebagai asetilen
dalam perdagangan atau sebagai pengelasan.

[sunting] Tata Nama


Semua anggota alkuna berakhiran -una.

[sunting] Rantai karbon lurus

Untuk alkuna rantai lurus, dinamakan sesuai dengan alkana dengan jumlah atom karbon
yang sama, namun diakhiri dengan -una. Berikut adalah alkuna dengan jumlah atom
karbon 2-10 disebut:

 Etuna, C2H2
 Propuna, C3H4
 Butuna, C4H6
 Pentuna, C5H8
 Heksuna, C6H10
 Heptuna, C7H12
 Oktuna, C8H14
 Nonuna, C9H16
 Dekuna, C10H18

[sunting] Rantai karbon bercabang

Untuk memberikan nama alkuna dengan rantai bercabang sama mirip dengan alkana
rantai bercabang. Namun "rantai utama" pada proses penamaan haruslah melalui ikatan
rangkap 3, dan prioritas penomoran dimulai dari ujung yang terdekat ke ikatan rangkap 3.

Artikel bertopik kimia ini adalah sebuah rintisan. Anda dapat membantu Wikipedia
  dengan mengembangkannya.
Alkyne
From Wikipedia, the free encyclopedia

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A 3D model of acetylene, the simplest alkyne


Not to be confused with Alkane or Alkene.

Alkynes are hydrocarbons that have a triple bond between two carbon atoms, with the
formula CnH2n-2. Alkynes are traditionally known as acetylenes, although the name
acetylene also refers specifically to C2H2, known formally as ethyne using IUPAC
nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic but tend to be
more reactive.

Contents
[hide]
 1 Chemical properties
 2 Structure and bonding
o 2.1 Terminal and internal alkynes
 3 Synthesis
 4 Reactions
o 4.1 Addition of hydrogen, halogens, and related reagents
o 4.2 Cycloadditions and oxidation
o 4.3 Reactions specific for terminal alkynes
 5 Alkynes in nature and medicine
 6 See also

 7 References

[edit] Chemical properties


Alkynes are characteristically more unsaturated than alkenes. Thus they add two
equivalents of bromine whereas an alkene adds only one equivalent. Other reactions are
listed below. Alkynes are usually more reactive than alkenes. They show greater
tendency to polymerize or oligomerize than alkenes do. The resulting polymers, called
polyacetylenes (which do not contain alkyne units) are conjugated and can exhibit
semiconducting properties.

[edit] Structure and bonding


In acetylene, the H-C≡C bond angles are 180°. By virtue of this bond angle, alkynes tend
to be rod-like. Correspondingly, cyclic alkynes are rare. Benzyne is highly unstable. The
C≡C bond distance of 121 picometers is much shorter than the C=C distance in alkenes
(134 pm) or the C-C bond in alkanes (153 pm).

Illustrative alkynes: a, two depictions of propyne, b, the naturally-occurring 1-


phenylhepta-1,3,5-heptatriyne, and c, the strained cycloheptyne.

The triple bond is very strong with a bond strength of 839 kJ/mol. The sigma bond
contributes 369 kJ/mol, the first pi bond contributes 268 kJ/mol and the second pi bond of
202 kJ/mol bond strength. Bonding usually discussed in the context of molecular orbital
theory, which recognizes the triple bond as arising from overlap of s and p orbitals. In the
language of valence bond theory, the carbon atoms in an alkyne bond are sp hybridized:
they each have two unhybridized p orbitals and two sp hybrid orbitals. Overlap of an sp
orbital from each atom forms one sp-sp sigma bond. Each p orbital on one atom overlaps
one on the other atom, forming two pi bonds, giving a total of three bonds. The remaining
sp orbital on each atom can form a sigma bond to another atom, for example to hydrogen
atoms in the parent acetylene]. The two sp orbitals project on opposite sides of the carbon
atom.

[edit] Terminal and internal alkynes

Internal alkynes feature carbon substituents on each acetylenic carbon. Symmetrical


examples include diphenyl acetylene and 3-hexyne. A representative unsymmetrical
internal alkyne is propiolic acid. Terminal alkynes have at least one hydrogen atom
bonded to a sp hybridized carbon (those involved in the triple bond. An example would
be methylacetylene (propyne using IUPAC nomenclature). Terminal alkynes and
acetylene are mildly acidic. The acidic hydrogen on terminal alkynes can be replaced by
a variety of groups resulting in halo-, silyl-, and alkoxoalkynes.

[edit] Synthesis
Commercially, the dominant alkyne is acetylene itself, which is used as a fuel and a
precursor to other compounds, e.g., acrylates. Hundreds of millions of kilograms are
produced annually by dehydrogenation of natural gas:

2 CH4 → HC≡CH + 3 H2

Propyne, also industrially useful, is also prepared by thermal cracking of hydrocarbons.


Most other industrially useful alkyne derivatives are prepared from acetylene, e.g. via
condensation with formaldehyde.[1]

Specialty alkynes are prepared by dehydrohalogenation of vicinal alkyl dihalides or vinyl


halides.[2] Metal acetylides can be coupled with primary alkyl halides. Via the Fritsch-
Buttenberg-Wiechell rearrangement, alkynes are prepared from vinyl bromides. Alkynes
can be prepared from aldehydes using the Corey-Fuchs reaction and from aldehydes or
ketones by the Seyferth-Gilbert homologation. In the alkyne zipper reaction, alkynes are
generated from other alkynes by treatment with a strong base.

[edit] Reactions
Featuring a reactive functional group, alkynes participate in many organic reactions.

[edit] Addition of hydrogen, halogens, and related reagents

Alkynes characteristically undergo reactions that show that they are "doubly
unsaturated," meaning that each alkyne unit is capable of adding two equivalents of H2,
halogens or related HX reagents (X = halide, pseudohalide, etc.). Depending on catalysts
and conditions, alkynes add one or two equivalents of hydrogen. Hydrogenation to the
alkene is usually more desirable since alkanes are less useful:

RC≡CR' + H2 → cis-RCH=CR'H

The largest scale application of this technology is the conversion of acetylene to ethylene
in refineries. The steam cracking of alkanes affords a few percent acetylene, which is
selectively hydrogenated in the presence of a palladium/silver catalyst. For more complex
alkynes, the Lindlar catalyst is widely recommended to avoid formation of the alkane, for
example in the conversion of phenylacetylene to styrene.[3]

Similarly, halogenation of alkynes gives the vinyl dihalides or alkyl tetrahalides:


RC≡CR' + 2 Br2 → RCBr2CRBr2

The addition of nonpolar E-H bonds across C≡C is general for silanes, boranes, and
related hydrides. The hydroboration of alkynes gives vinylic boranes which oxidize to the
corresponding aldehyde or ketone.

Hydrohalogenation gives the corresponding vinyl halides or alkyl dihalides, again


depending on the number of equivalents of HX added. The addition of water to alkynes is
a related reaction except the initial enol intermediate converts to the ketone or aldehyde.
Illustrative is the hydration of phenylacetylene gives acetophenone,[4] and the
(Ph3P)AuCH3-catalyzed hydration of 1,8-nonadiyne to 2,8-nonanedione:[5]

PhC≡CH + H2O → PhCOCH3


HC≡CC6H12C≡CH + 2H2O → CH3COC6H12COCH3

[edit] Cycloadditions and oxidation

Alkynes undergo diverse cycloaddition reactions. Most notable is the Diels-Alder


reaction with 1,3-dienes to give 1,4-cyclohexadienes. This general reaction has been
extensively developed and electrophilic alkynes are especially effective dienophiles. The
"cycloadduct" derived from the addition of alkynes to 2-pyrone eliminates carbon dioxide
to give the aromatic compound. Other specialized cycloadditions include multicomponent
reactions such as alkyne trimerisation to give aromatic compounds and the
[2+2+1]cycloaddition of an alkyne, alkene and carbon monoxide in the Pauson–Khand
reaction. Non-carbon reagents also undergo cyclization, e.g. Azide alkyne Huisgen
cycloaddition to give triazoles. Cycloaddition processes involving alkynes are often
catalyzed by metals, e.g. enyne metathesis and alkyne metathesis, which allows the
scrambling of carbyne (RC) centers:

RC≡CR + R'C≡CR' 2 RC≡CR'

Oxidative cleavage of alkynes proceeds via cycloaddition to metal oxides. Most


famously, potassium permanganate converts alkynes to a pair of carboxylic acids.

[edit] Reactions specific for terminal alkynes

In addition to undergoing the reactions characteristic of internal alkynes, terminal alkynes


are reactive as weak acids, with pKa values (25) between that of ammonia (35) and
ethanol (16). The acetylide conjugate base to be stabilized as a result of the high s
character of the sp orbital, in which the electron pair resides. Electrons in an s orbital
benefit from closer proximity to the positively charged atom nucleus, and are therefore
lower in energy. Treatment of terminal alkynes with a strong base gives the
corresponding metal acetylides:

RC≡CH + MX → RC≡CM + HX (MX = NaNH2, LiBu, RMgX)


The reactions of alkynes with certain metal cations, e.g. Ag+ also gives acetylides. Thus,
few drops of diamminesilver(I) hydroxide (Ag(NH3)2OH) reacts with terminal alkynes
signaled by formation of a white precipitate of the silver acetylide. Acetylide derivatives
are synthetically useful nucleophiles that participate in C-C bond forming reactions, as
illustrated in the area called "Reppe Chemistry".

In the Favorskii reaction, terminal alkynes add to carbonyl compounds to give the
hydroxyalkyne. Coupling of terminal alkynes to give di-alkynes is effected in the Cadiot-
Chodkiewicz coupling, Glaser coupling, and the Eglinton coupling reactions. Terminal
alkynes can also be coupled to aryl or vinyl halides as in the Sonogashira coupling.

[edit] Alkynes in nature and medicine


Alkynes are relatively rare in nature. Triynes, species with the linkage RC≡C-C≡C-
C≡CR', occur in certain plants (Ichthyothere, Chrysanthemum, and other members of the
Asteraceae family). These compounds are highly bioactive, e.g. as nematocides.[6] 1-
Phenylhepta-1,3,5-triyne is illustrative of a naturally occurring triyne.

Alkynes occur in some pharmaceuticals, including the contraceptive norethynodrel. A


carbon-carbon triple bond is also present in marketed drugs such as the antiretroviral
Efavirenz and the antifungal Terbinafine. Molecules called ene-diynes feature a ring
containing an alkene ("ene") between two alkyne groups ("diyne"). These compounds,
e.g. calicheamicin, are some of the most aggressive antitumor drugs known, so much so
that the ene-diyne subunit is sometimes referred to as a "warhead." Ene-diynes undergo
rearrangement via the Bergman cyclization, generating highly reactive radical
intermediates that attack DNA within the tumor.[7]
Alkuna
(Kimia Kelas 2 > Hidrokarbon)
236h

< Sebelum Sesudah >

Alkuna merupakan deret senyawa hidrokarbon tidak jenuh yang dalam tiap
molekulnya mengandung satu ikatan rangkap 3 diantara dua atom C yang
berurutan. Untuk membentuk ikatan rangkap 3 atau 3 ikatan kovalen diperlukan 6
elektron, sehingga tinggal satu elektron pada tiap-tiap atom C tersisa untuk
mengikat atom H. Jumlah atom H, yang dapat diikat berkurang dua, maka rumus
umumnya menjadi
CnH2n+2 - 4H = CnH2n-2

Seperti halnya alkena, alkuna juga mempunyai suku pertama dengan harga n = 2,
sehingga rumus molekulnya C2H2, sedang rumus strukturnya H - C C - H. Senyawa
alkuna tersebut mempunyai nama etuna atau dengan nama lazim asetilena.
Asetilena merupakan suatu gas yang dihasilkan dari reaksi karbon dengan air dan
banyak digunakan oleh tukang las untuk menyambung besi.

CaC2 (s) + 2 H20 (l)  C2H2 (g) + Ca(OH)2 (aq)


karbida asetilena

Tata nama alkuna sama dengan alkana atau alkena, bagian pertama menunjuk pada
jumlah sedang bagian kedua adalah akhiran -una, tetapi suku pertamanya juga
mempunyai n = 2 seperti alkena. Etuna merupakan suku alkuna satu-satunya yang
dapat dibuat. Suku-suku alkuna lain sering diberi nama atau dianggap sebagai
turunan etuna. Jadi propuna disebut metil asetilena.

Seperti pada alkana, suku-suku rendah pada alkena dan alkuna pun hanya
mempunyai satu rumus struktur, tetapi pada suku ketiga (jangan lupa harga n-nya
4) dapat kita tuliskan lebih dari satu rumus struktur yaitu ,

pada alkena

1-butena
CH2=CH-CH2-CH3
2-butena
CH3-CH=CH-CH3
CH2=C-CH3
2-metil-1-propena |
CH3

pada alkuna

CH3C-CH2-CH3
1-butuna
CH3-CC-CH3 2-butuna
Jadi peristiwa isomeri terjadi pula pada alkena dan alkuna, bahkan penyebabnya
dua. Kalau pada alkana hanya pada rantainya berbeda (disebut isomeri rantai), pada
alkena dan alkuna dapat pula disebabkan ikatan rangkapnya berpindah tempat
(disebut isomeri posisi) karena itu letak ikatan rangkap pada suku-suku alkena dan
alkuna yang lebih tinggi selalu diberi nomor seperti terlihat di atas.
Alkuna
Ditulis oleh Sukarmin pada 29-09-2009

Alkuna merupakan hidrokarbon tak jenuh yang mempunyai ikatan rangkap tiga C=C.
Suku alkana yang paling kecil terdiri dari dua atom C, yaitu etuna. Nama alkuna sesuai
dengan nama alkana dengan mengganti akhiran – ana menjadi -una.

Nama Struktur Rumus molekul


Etena CH=CH C2H4
Propena CH=C-CH3 C3H4
Butena CH=C-CH2-CH3 C4H6
Pentena CH=C- CH2- CH2?-CH3 C5H8

Dari tabel diatas rumus molekul secara umum dapat dirumuskan:

CnH2n-2

Tata nama alkena

Tata nama alkuna menurut IUPAC sama dengan tatanama alkena, lang-kah-langkah
untuk memberi nama alkuna adalah sebagai berikut:

1. Tentukan rantai induk, yaitu rantai karbon terpanjang dari ujung satu ke ujung yang
lain yang melewati ikatan rangkap, berilah nama alkuna sesuai jumlah atom C pada rantai
induk.

2. Penomoran.            Penomoran dimulai dari ujung rantai induk yang terdekat dengan
rangkap.

3. Jika terdapat cabang berilah nama cabang dengan alkil sesuai jumlah atom C cabang
tersebut. Jika terdapat lebih dari satu cabang, aturan penamaan sesuai dengan aturan pada
tatanama alkana.

4. Urutan penamaan: nomor cabang-nama cabang-nomor rangkap-rantai induk.

Contoh:
Penentuan rantai induk salah Meskipun mempunyai rantai terpanjang, tetapi tidak
melewati rangkap.

ISOMER ALKUNA

Etuna (C2H2), propena (C3H4) tidak mempunyai isomeri katena hanya ada satu struktur.

Isomer dari butuna (C4H6):

Isomer pentuna (C5H8)


Sifat Alkuna
Ditulis oleh Sukarmin pada 28-09-2009

Sifat fisis

Sifat fisis alkuna, yakni titik didih mirip dengan alkana dan alkena. Semakin tinggi suku
alkena, titik didih semakin besar. Pada suhu kamar, tiga suku pertama berwujud gas, suku
berikutnya berwujud cair sedangkan pada suku yang tinggi berwujud padat.

Tabel 6. Beberapa sifat fisik alkuna

Titik F
Nama alkena Rumus Mr Titik leleh Kerapatan
didih pa
molekul (oC) (g/Cm3 )
(0 C) 25
Etuna
C2H2 26 -81 -85 - G
Propuna
C3H4 40 -103 -23 - G
1-Butuna
C4H6 54 -126 8 - G
1-Pentuna
C5H8 68 -90 40 0,690 C
1-Heksuna C6H10 -132 71 0,716 C
82
1-Hepuna C7H12 -81 100 0,733 C
96
1-Oktuna C8H14 -79 126 0,740 C
110
1-Nonusa C9H16 -50 151 0,766 C
124
1-Dekuna C10H18 -44 174 0,765 C
138

Sifat kimia

Adanya ikatan rangkap tiga yang dimiliki alkuna memungkinkan terjadinya reaksi adisi,
polimerisasi, substitusi dan pembakaran

1. reaksi adisi pada alkuna

o Reaksi alkuna dengan halogen (halogenisasi)


Perhatikan reaksi di atas, reaksi pada tahap 2 berlaku aturan markonikov.

o     Reaksi alkuna dengan hidrogen halida

Reaksi di atas mengikuti aturan markonikov, tetapi jika pada reaksi alkena dan alkuna
ditambahkan peroksida maka akan berlaku aturan antimarkonikov. Perhatikan reaksi
berikut:

o Reaksi alkuna dengan hidrogen

2. Polimerisasi alkuna

3. Substitusi alkuna Substitusi (pengantian) pada alkuna dilakukan dengan menggantikan


satu atom H yang terikat pada C=C di ujung rantai dengan atom lain.
4. Pembakaran alkuna Pembakaran alkuna (reaksi alkuna dengan oksigen) akan
menghasilkan CO2 dan H2O.

2CH=CH + 5 O2 � 4CO2 + 2H2O

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