ALKENA DAN ALKUNA

Alkane RCH2CH2R CnH2n+2

This is the maximum H/C

ratio for a given number of
carbon atoms.

Alkene RCH=CHR

CnH2n

Each double bond reduces

the number of hydrogen
atoms by 2.

Alkyne
RCCR
Alkuna

CnH2n-2

Each triple bond reduces the

number of hydrogen atoms
by 4.

Alkena dan Alkuna

Alkena:

Seny. hidrokarbon jenuh yg

mengandung ikatan rangkap 2

H2C

H2C

CH2

CHCH2CH3

1-Butena

Etena

Sikloheksena

Alkuna:

Siklopentena

Seny hidrokarbon tak jenuh yg

mengandung ikatan rangkap 3
HC

CH

Etuna

H3CC

CCH3

2-Butuna

IUPAC Rules for Alkene and

Cycloalkene Nomenclature
1. The ene suffix (ending) indicates an alkene or cycloalkene.
2. The longest chain chosen for the root name must include both carbon
atoms of the double bond.
3. The root chain must be numbered from the end nearest a double bond
carbon atom. If the double bond is in the center of the chain, the nearest
substituent rule is used to determine the end where numbering starts.
4. The smaller of the two numbers designating the carbon atoms of the
double bond is used as the double bond locator. If more than one double
bond is present the compound is named as a diene, triene or equivalent
prefix indicating the number of double bonds, and each double bond is
assigned a locator number.
5. In cycloalkenes the double bond carbons are assigned ring locations #1
and #2. Which of the two is #1 may be determined by the nearest
substituent rule.
6. Substituent groups containing double bonds are:
H2C=CH Vinyl group
H2C=CHCH2 Allyl group

IUPAC Rules for Alkyne

Nomenclature

1. The yne suffix (ending) indicates an alkyne or cycloalkyne.

2. The longest chain chosen for the root name must include both carbon
atoms of the triple bond.
3. The root chain must be numbered from the end nearest a triple bond
carbon atom. If the triple bond is in the center of the chain, the nearest
substituent rule is used to determine the end where numbering starts.
4. The smaller of the two numbers designating the carbon atoms of the
triple bond is used as the triple bond locator.
5. If several multiple bonds are present, each must be assigned a locator
number. Double bonds precede triple bonds in the IUPAC name, but the
chain is numbered from the end nearest a multiple bond, regardless of its
nature.
6. Because the triple bond is linear, it can only be accomodated in rings
larger than ten carbons. In simple cycloalkynes the triple bond carbons are
assigned ring locations #1 and #2. Which of the two is #1 may be
determined by the nearest substituent rule.
7. Substituent groups containing triple bonds are:
HCC Ethynyl group
HCCHCH2 Propargyl group

Tatanama Alkena dan Alkuna

Mengacu sistem IUPAC, alkena diberi nama dg mengganti akiran

ana dari alkana dg ena (jika memp 2 ikatan rangkap maka disebut
diena, sementara hidrokarbon dg 3 ikatan rangkap 2 disebut triena.
Alkuna diberi akhiran una
Rantai terpanjang: rantai utama yg mengandung ikatan rangkap 2
atau 3
Pemberian nomor dimulai dari C ujung yg paling dekat dg ikatan
rangkap
CH3

CH3
H3CH2CHC

H2C

CCH3

CCH3

CH2

2-metil-1,3-butadiena

2-metil-2-pentena
H3CC

CCH

H3C
C

2-Butuna
H

H3CC

C
CH3

trans-2-butena

CCH2CH3

CH

Sifat Fisika Alkena dan Alkuna

Alkena

dan alkuna relatif lebih reaktif

daripada alkana, namun tidak luar biasa
polar
Dg demikian sifat fisiknya hampir sama
dg alkana
Kepolaran alkuna > alkena > alkana
Baik alkana, alkena, dan alkuna tidak
larut dlm air

Sintesis Alkena
Alkena dpt disintesis dari alkilhalida dan basa kuat melalui

reaksi eliminasi bimolekuler(E2)

HO

H2
C

Kalor
CHCH3

HOH

H2C

CHCH3

Br

(CH3)2CHOH

H2SO4
o

100 C

H3CHC

CH2

+ H2O

Br-

Mekanisme Reaksi Sintesis Alkena

Tahap 1. protonasi
OH

OH2

H
H3C

CH

CH3

H3C

CH

CH3

-H2O

H3C

H
C

CH3

Tahap 2. Lepasnya H+
H
H2C

H
C

H
CH3

H2C

H
C

CH3

-H+

H2C

H
C

CH3

Sintesis Alkuna
Alkuna dpt disintesis dari alkilhalida dan basa kuat melalui

2 reaksi eliminasi bimolekuler(E2)

Br
RHC

Br

Br

OR dalam etanol

CHR

-HBr

RHC

CR

Br
RHC

CR

NaNH2, KOH pekat + Kalor

-HBr

RC

CR

Adisi Halogen Halida pada Alkena dan

Alkuna
Reaksi adisi kebalikan dari reaksi eliminasi
H2C

HC

CH2

CH

CH3CH2X
etil halida

HX

HX

H2C

CHX

HX

CH3CHX2

Mekanisme reaksi adisinya (substitusi elektrofilik)

H
H2C

CH2

Cl

CH2

H
H2C

H2C

CH2

+ Cl

H2C

CH2
Cl

+ Cl

Refresh

H3CHC

CH2

HCl
(adisi)

Aturan Markonikov
Dalam reaksi adisi HX kepada alkena tak-simetris, H+ dari

HX menuju ke karbon berikatan rangkap yg telah lebih

banyak memiliki hidrogen
Contoh
Cl

H3CHC

CH2

HCl

H3CHC

H
CH2

bukan H CHC
3

Cl

2-kloro propana
Br
(H3C)2C

CHCH3

HBr

(H3C)2C

CH2

CHCH3
H

Penalaran Aturan Markonikov

Penalaran aturan Markonikov dilakukan dg mempelajari

mekanisme reaksi adisi HX pada alkena, dg didasarkan

pada kestabilan karbokation
Tingkat kestabilan karbokation tersier > sekunder > primer
H+
H3CHC

H
H3CHC

CH2

H3CH2C

CH2

Karbokation (C+) primer tdk stabil

Keadaan transisi
H

H
H3CHC

CH2

CH2

H3CHC

CH2

Keadaan transisi

H3C

C
H

CH3

C+ sekunder lebih stabil

Jadi
Cl

H
H3CHC

CH2

Cl
H3C

C
H

CH3

H3CHC

CH2
H

2-kloro propana

H
(H3C)2C

CHCH3

Br

(H3C)2C

CH2CH3

(H3C)2C

CHCH3
H

Adisi Halogen (Br2 dan Cl2) pada

Alkena dan Alkuna
Jika Br2 dan ikatan pi mulai bergabung, elektron pi dapat

menyebabkan Br2 terpolarisasi sehingga ujung molekul

bromida sebagian positif dan ujung lainya (parsial)
negatif

Langkah 1.
R

R
C

Br

Br
C

Br

Br

R
C

ion bromonium

Langkah 2. masuknya Br

Br

Br

Br

C
R

dibromo alkana

Br

Adisi Halogen dan Air

Jika alkena + Br2 ato Cl2 + air

1,2-halohidrin
contoh
H CHC
3

Camp. Adisi
OH

CH2

Br2

+ H2O

H3CHC

Mekanismenya:
Br
H3CHC

CH2

1-Bromo-2-propanol
(1,2-bromohidrin)

Br
CH2

Br

Br

Br

-Br

H3CHC

OH
CH2

H3CHC

CH2

OH
H

-H+
Br
H3CHC
OH

CH2

HBr

Contoh soal

Selesaikan reaksi berikut dg menunjukkan

intermediet bermuatan positif!
CH3

a.

H3CHC

CCH3

+ Br2

CCl4

CH3

b.

H3CHC

CCH3

+ Br2

+ H2 O

Adisi H2SO4 dan H2O pada alkena dan

alkuna
H2SO4 berfungsi sebagai katalisator yg merupakan

seny asam pengadisi ikatan rangkap

Mekanisme reaksinya:
H

OSO3H

H3CHC

CH2

H+

+ OSO3H
CH3CHCH3
OH

CH3CHCH3
OH
H

-H

CH3CHCH3
OH

2-propanol

Contoh Soal
Selesaikan reaksi berikut dan apa produk utamanya!

a.

H3CH2CHC

CH2

CH2CH3

b.

+ H2O

H+
H+

+ H2O

Tuliskan persamaan reaksi yg memperlihatkan bagaimana

membuat senyawa berikut:
OH

H3C

CH

CH2CH2CH2CH3