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<img src="/icons/checkmark_gray.svg" alt="/icons/checkmark_gray.svg"
width="40px" /> **Alkenes :**
- Alkenes are **unsaturated hydrocarbons ( C = C )**
→ Addition reactions to form saturated **C-C bonds.**
- C = C is a region of **high electron density.** → reaction with **electron
deficient particles. ⇒ Electrophiles**
- Alkanes can be made by a series of reactions including :
- Elimination
- Dehydration
- Cracking
**Elimination Reaction :**
- Alkenes can be produced from the elimination reaction of a **halogenoalkane**
- An **elimination reaction** is one in which a **small molecule** is lost
- In the case of halogenoalkanes, the small molecule that is eliminated is a
hydrogen halide, HX, where X is the halogen
- The halogenoalkane is heated with **ethanolic sodium hydroxide.**
- The eliminated H+ in HBr reacts with the ethanoic OH- to form water.
[[Link]]([Link]
[Link]/1521f175-26c1-4eac-ad50-03863dc626e2/0da4aa12-9952-4e71-90c3-
126f02610194/[Link])
- The eliminated Br- in HBr reacts with Na+ to form NaBr.
- The eliminated Br- in HBr reacts with Na + to form NaBr .
[[Link]]([Link]
[Link]/1521f175-26c1-4eac-ad50-03863dc626e2/aa1e4045-d546-4093-84f1-
42ade54954d2/[Link])
**Dehydration reaction :**
- Alkenes can also be produced from the elimination reaction of alcohols in which a
water molecule is lost
- This is called a **dehydration** reaction
- Alcohol vapour is passed over a hot catalyst of **aluminium oxide power
( Al2O3 )**
- Concentrated acid, pieces of porous pot or pumice can also be used as
catalysts.
[[Link]]([Link]
[Link]/1521f175-26c1-4eac-ad50-03863dc626e2/f4baf625-
70eb-431f-b42f-13e899278602/[Link])
![[Link]]([Link]
26c1-4eac-ad50-03863dc626e2/be5b7b3d-964f-418c-9dd8-a4202e253bf1/[Link])
- The smaller alkenes ( such as ethene, propene and butene ) are all **gases** at
room temperature and can be **collected** over **water.**
![[Link]]([Link]
[Link]/1521f175-26c1-4eac-ad50-03863dc626e2/32bae4e7-540f-4fdb-81fe-
2a52ea22ea7f/[Link])
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<img src="/icons/checkmark_gray.svg" alt="/icons/checkmark_gray.svg"
width="40px" /> **Alkene Reactions :**
- Electrophilic reactions are typical to **alkenes .**
- Electrophiles include **H+** or **Br +**
**Electrophilic reaction of HBr to ethene :**
- A molecule of hydrogen bromide ( HBr ) is **polar** as the hydrogen and bromine
atoms have different **electronegativities.**
- The bromine has a stronger pull on the electrons in the H-Br bond.
⇒ As a result of this, the Br atom has a partial negative and the H atom a partial
positive charge
[[Link]]([Link]
[Link]/1521f175-26c1-4eac-ad50-03863dc626e2/f31a2736-9023-4f6d-84ec-
c068c879ac28/[Link])
- In an addition reaction, the H atom acts as an electrophile and accepts a pair of
electrons from the C-C bond in the alkene.
- This results in the formation of a highly reactive carbocation intermediate which
reacts with the bromide ion, Br-
- For example, the mechanism for the electrophilic addition of hydrogen bromide and
ethene is :
[[Link]]([Link]
[Link]/1521f175-26c1-4eac-ad50-03863dc626e2/170c7c05-c5fd-4b55-8c67-
ea9e411b9f75/[Link])
**Electrophilic reaction of bromine :**
- Bromine ( Br2 ) unlike HBr is a **non-polar** molecule as both atoms have similar
electronegativities and therefore equally share the electrons in the covalent bond.
- However, when a bromine molecule gets closer to the double bond of an alkene, the
**high electron density** in the double bond repels the electron pair in Br-Br away
from the closest Br atom.
- As a result of this, the closest Br atom to the double bond is slightly positive
and the further Br atom is slightly negatively charged.
- In an addition reaction, the closest Br atom acts as an electrophile and accepts
a pair of electrons from the C - C bond in the alkene.
- The Br - Br bond breaks heterolytically, forming a Br- ion
- This results in the formation of a highly reactive **carbocation intermediate**
which reacts with the Br- ( nucleophile )
[[Link]]([Link]
[Link]/1521f175-26c1-4eac-ad50-03863dc626e2/30d2b2d8-63c8-44ec-a2f2-
714e42b72333/[Link])
**Electrophilic reaction with steam & Hydrogenation :**
**Hydrogenation :**
- Reaction of alkene and hydrogen to form an alkane
- Use of catalyst **Platinum** or **Nickel**
- Temperature of about **140 degrees Celsius.**
![[Link]]([Link]
4eac-ad50-03863dc626e2/c79b848a-bb9e-47b8-9d43-2ffcd1610f81/[Link])
**Hydration of Ethene :**
- React with steam
- Temperature : 320 degrees Celsius
- Using concentrated phosphoric acid ( H3PO4 ) catalyst
![[Link]]([Link]
4eac-ad50-03863dc626e2/d8c6c192-e221-4cf0-9180-2075cd5e1a88/[Link])
**Oxidation alkenes using KMnO4**
- Alkenes can also be **oxidised** by **acidified potassium manganate (VII)**
(KMnO4) which is a very powerful **oxidising agent.**
- Alkenes can be oxidised by both **hot** and **cold** KMnO4, which will result in
different products being formed.
**Alkene with cold dilute KMnO4**
- The **pale purple** solution → **colourless**
- Forms a product called **diol.**
![[Link]]([Link]
4eac-ad50-03863dc626e2/70ffdc7d-1f3f-4976-a204-cf2599f4d8fb/[Link])
**Alkene with hot concentrated KMnO4**
- harsher conditions which cause the C-C double bond to completely break.
- The O-H groups in the diol formed are further oxidised to **ketones, aldehydes,
carboxylic acids** or **carbon dioxide gas.**
![[Link]]([Link]
4eac-ad50-03863dc626e2/66b36153-3b39-4798-8e0d-e709990c70d4/[Link])
- The reactions of alkenes with hot concentrated KMnO can be used to determine the
position of the double bond in larger alkenes
![[Link]]([Link]
[Link]/1521f175-26c1-4eac-ad50-03863dc626e2/f60fec3e-
9ff6-435d-9d35-9911aaca7181/3.2-Hydrocarbons-Determining-Position-of-Double-
[Link])
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<img src="/icons/checkmark_gray.svg" alt="/icons/checkmark_gray.svg"
width="40px" /> **Markovnikov’s Rule :**
- **Carbocations** are positively charged carbon atoms with only **three covalent
bonds** instead of four.
**Inductive Effect :**
- The **alkyl group** attached to the positively charged carbon atoms are ‘electron
donating groups’
- This is also known as the **inductive effect** of alkyl groups
- The inductive effect is indicated by the use of arrowheads on the bonds to show
the alkyl groups pushing electrons towards the positively charged carbon. ⇒ **Less
positively charged carbocation.**
⇒ **Tertiary carbocations** are the most stable as they have three electron-
donating alkyl groups which energetically stabilise the carbocation.
- Due to the positive charge on the carbon atom, carbocations are still
**electrophiles.**
![[Link]]([Link]
[Link]/1521f175-26c1-4eac-ad50-03863dc626e2/f9892524-
a329-4d6a-bde0-a0fab7607969/[Link])
**Markovnikov’s Rule :**
- Markovnikov’s rule predicts the outcome of electrophillic addition reactions and
states that :
- In an electrophillic addition reaction of a hydrogen halide (HX) to an
alkene, the halogen ends up bonded to the most substituted carbon atom.
- In an electrophillic addition reaction of an interhalogen to an alkene, the
most electronegative halogen ends up bonded to the most substituted carbon atom.
- Markovnikov addition applies to electrophillic addition reactions with
**unsymmetrical alkenes.**
- Markovnikov addition favours the formation of the **major product.**
- Anti-Markovnikov addition favours the formation of the minor product.
- In electrophillic addition ractions, an electrophile reacts with the **double
bond of alkenes** ( as previously discussed )
[[Link]]([Link]
[Link]/1521f175-26c1-4eac-ad50-03863dc626e2/9d192aa1-a4c0-4d6b-93db-
b4102ba157f6/[Link])
- The electrophile can attach in 2 possible ways :
1. Breaking the C = C bond and attaching to the least substituted carbon
1. This will give the **most** stable carbocation as an intermediate that will
form the **major** product
2. Breaking the C = C bond and attaching to the most substituted carbon
1. This will give the **least** stable carbocation as an intermediate that will
form the **minor** product.
[[Link]]([Link]
[Link]/1521f175-26c1-4eac-ad50-03863dc626e2/f3972984-
b3ef-49a4-8bfb-e1508d3ad6af/[Link])
- The nucleophile ưill bond to the posiruve carbon atom of the **carbocation.**
- The more stable carbocation produces the major product.
- The less stable carbocation produces the minor product.
[[Link]]([Link]
[Link]/1521f175-26c1-4eac-ad50-03863dc626e2/c5103437-d374-4281-a04b-
aa26165392bd/[Link])
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<aside>
<img src="/icons/checkmark_gray.svg" alt="/icons/checkmark_gray.svg"
width="40px" /> **Addition Polymerisation :**
- Addition polymerisation is the reaction of many monomers containing at least one
double C-C bond to form the long-chain polymers as the only product.
- **Monomers** are small, reactive molecules that react togerther to make the
polymer
- A **polymer** is a long-chain molecule made up of many **repeating units**
( monomers )
- In an addition polymerisation reaction, the C-c double bond is broken to link
together the monomers and form a polymer.
![[Link]]([Link]
[Link]/1521f175-26c1-4eac-ad50-03863dc626e2/c2bfb641-
bbc7-48ba-9972-45d6d43ba543/[Link])
![[Link]]([Link]
[Link]/1521f175-26c1-4eac-ad50-03863dc626e2/6b49fb9d-
ebfd-4b18-80f1-77a0242803c6/[Link])
- Other alkenes and **substituted** alkenes can also polymerise to make polymers
with different **properties**
- E.g. poly(chloroethene), also known as PVC is the most versatile plastic used.
![[Link]]([Link]
1521f175-26c1-4eac-ad50-03863dc626e2/22ef0f19-43c9-4abd-8f1e-a1f3abcb7b78/3.2-
[Link])
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