Chemistry, Third edition

(Wang) #1
ALKENES

Hydrogen (H 2 ) H–H


The addition of hydrogen to an alkene is called hydrogenation and the product is an


alkane. Hydrogenation is carried out in the presence of a catalyst (nickel, palladium


or other platinum metals) and at a high pressure of hydrogen:


HH
Ni ||
RCH=CH 2 H—H—RCH—CH 2
500 °C

Hydrogen halides (HCl) H–Cl, (HBr) H–Br and (HI) H–I


The gaseous hydrogen halides react directly with the alkene to produce halogenoalkanes:


Cl H
||
RCH=CH 2 H—ClRCH—CH 2

Sulfuric acid (H 2 SO 4 ) H–OSO 3 H


Alkenes react with cold, concentrated sulfuric acid to form alkyl hydrogensulfates:


OSO 3 HH
||
RCH=CH 2 H—OSO 3 HRCH——CH 2


  1. Oxidation


Alkenes can be oxidized by cold, slightly alkaline potassium permanganate (man-


ganate(VII)) to make substances called 1,2 diols, containing two OH groups on


adjacent carbon atoms. The potassium permanganate solution turns from purple to


brown. This is another test (theBaeyer test) that is often used to detect unsatura-


tion in a hydrocarbon:


OH OH
KMnO 4 ||
CH 2 =CH 2 —CH 2 —CH 2
ethane-1,2-diol


  1. Polymerization


Under the right conditions, alkenes will undergo addition reactions with each other.


The reaction is called polymerization. For example, many ethene molecules will join


together to form polythene – the double bonds break and the molecules link up:


O 2 , heat, pressure
n(CH 2 =CH 2 ) —————···CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 ···
wheren= a large number or catalyst
(typically 20 000)

The product can also be written as


···(—CH 2 —CH 2 —)n···

Long chain molecules called polymers are formed from the small ethene


molecules, themonomers. The long, thin molecules of a polymer may also be called


linear macromolecules. Polythene is an unreactive solid; it can be easily moulded


and is used for plastic bags, bottles, washing-up bowls and plastic piping. The word


‘plastic’ means ‘easily moulded’. Substituted ethene molecules can undergo the same


addition reaction to give other polymers:


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