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Oxidation and Addition Reactions of Alkenes

The document summarizes various reaction types of alkenes, including: 1. Addition reactions such as hydrohalogenation, hydration, halogenation, and hydrogenation. 2. Oxidation reactions using strong oxidizers like KMnO4 and O3, which can cleave double bonds or hydroxylate carbons, and epoxidation using m-CPBA. 3. Polymerization reactions where small alkene units combine through an initiator like a peracid to form polymers.

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Lara Alhaddad
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70 views14 pages

Oxidation and Addition Reactions of Alkenes

The document summarizes various reaction types of alkenes, including: 1. Addition reactions such as hydrohalogenation, hydration, halogenation, and hydrogenation. 2. Oxidation reactions using strong oxidizers like KMnO4 and O3, which can cleave double bonds or hydroxylate carbons, and epoxidation using m-CPBA. 3. Polymerization reactions where small alkene units combine through an initiator like a peracid to form polymers.

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Lara Alhaddad
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Reactions of alkenes:

i) Addition Reactions:
Previously, we have covered all types of addition
reactions.
1) Addition of HX (Hydrohalogenation)
2) Addition of H2O (Hydration) in Markovnikov’s
manner and anti-Markovnikov’s manner.
3) Addition of X2 (Halogenation) [as anti-addition
mechanism]
4) Addition of H2(Hydrogenation) [as syn-addition
mechanism]
ii) Oxidation Reactions
A) Oxidation by KMnO4
1) In acidic medium (H2O/H+)
KMnO4 is a powerful oxidizing agent which oxidize alkenes
leading to double bond cleavage. In this reaction the KMnO4
reagent attack the double bond and break the double bond
from the middle leading to carbonyl compounds through a
complicated mechanism. The General reaction is as follows;
Notice that; if any of the R-groups will be replaced by –H, the reaction will
proceeds normal but the resulted aldehydes RCH=O will be further
oxidized to carboxylic acids RCOOH because the KMNO4 in acidic medium
is very strong oxidizing agent as seen in the following examples.


B) Oxidation by KMnO4 in basic medium (H2O/OH-).
 In this reaction the KMnO4 is less powerful than in acidic
medium. The double bond will not completely breakage,
but both carbons of the double bond will be hydroxylated
leading to the cis-vicinal diols (two alcohol groups beside
each other in same direction) (see the general example)
 More examples:
C) Oxidation by ozone O3:
Oxidation by ozone O3 is the same as by KMnO4 in acidic medium, but
without further oxidation to aldehydes that formed. For example;
D) Epoxidation of alkenes by m-CPBA (meta-Chloroperoxybenzoic
Acid. In this case alkenes are oxidized to form epoxides.

EX 1:

EX 2:
 Notice that, the resulted epoxide reacts in acidic
medium (H2O/ H+) to give trans-1,2-diol in which the
two -OH groups are in opposite direction as follows:

Notice that, if the two groups (as -OH groups) are


neighboring to each other, or on adjacent carbons, then
they are called vicinal. (in this case vicinal diol)
‫‪‬‬ ‫‪iii) Polymerization of alkenes:‬‬
‫‪‬‬ ‫‪this means that small units are coming together to form a‬‬
‫‪polymer (multi-units). This process needs an initiator which‬‬
‫‪initiate the process. In this reaction type the initiator is a‬‬
‫‪peracid.‬‬

‫‪‬‬ ‫بلمرة األلكينات‪ :‬وتعني اتحاد مجموعة من جزيئات األلكين مع بعضها‬


‫البعض لتكون البوليمر‪ .‬وهذه العملية بحاجة الى بادئ وهو الذي يجعل‬
‫التفاعل يبدأ‪ .‬وفي التفاعالت الخاصة باأللكينات يكون هو البيراسيد وله‬
‫أشكال مختلفة منها البيربنزويك أسيد كما في المثال التالي‪.‬‬
 Ex: Ethylene (ethene) can be polymerized to form
polyethylene as a polymer.

This reaction proceeds in three main steps; initiation, propagation


and termination.
.‫ البداية ثم المتسلسلة ثم النهاية‬:‫وهذا التفاعل يتم بالخطوات التالية‬

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