Chapter 3 Alkenes

ORGANIC CHEMISTRY 1 CHM 207 CHAPTER 3: ALKENES NOR AKMALAZURA JANI

ALKENES ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]

IUPAC RULES ,[object Object],This chain contains 6 carbon atoms

[object Object],This is the longest continuous chain. Select it as the parent compound. Name the parent compound octene. This chain contains 8 carbon atoms

RULE 3. Number the carbon chain of the parent compound starting with the end nearer to the double bond. Use the smaller of the two numbers on the double-bonded carbon to indicate the position of the double bond. Place this number in front of the alkene name.

IUPAC RULES This end of the chain is closest to the double bond. Begin numbering here.

IUPAC RULES The name of the parent compound is 1-octene. 8 7 4 3 2 1 6 5

RULE 4. Branched chains and other groups are treated as in naming alkanes. Name the substituent group, and designate its position on the parent chain with a number.

IUPAC RULES This is an ethyl group. 8 7 4 3 2 1 6 5 The ethyl group is attached to carbon 4. 4 4-ethyl-1-octene

[object Object],[object Object],[object Object],[object Object],[object Object]

ALKENES AS SUBSTITUENTS ,[object Object],[object Object]

CYCLOALKENES ,[object Object],[object Object],[object Object],[object Object]

NOMENCLATURE OF cis-trans ISOMERS ,[object Object],[object Object]

PHYSICAL PROPERTIES OF ALKENES ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]

[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]

[object Object],[object Object],[object Object],Vector sum = propene, μ = 0.33 D cis -2-butene, bp 4 o C Vector sum = 0 propene, μ = 0 trans -2-butene, bp 1 o C Vinylic bonds

[object Object],[object Object],Vector sum = propene, μ = 0.33 D cis -2-butene, bp 4 o C Vector sum = 0 propene, μ = 0 trans -2-butene, bp 1 o C

PREPARATION OF ALKENES ,[object Object],[object Object],conc. H 2 SO 4 R-CH 2 -CH 2 -OH R-CH=CH 2 + H 2 O ii) Dehydrohalogenation of haloalkanes NaOH/ethanol R-CH 2 -CH 2 -X reflux R-CH=CH 2 + HX NaOH can be replaced by KOH

[object Object],[object Object],Dehydration of alcohols Dehydrohalogenation of haloalkanes

REACTIVITY OF ALKENES ,[object Object],[object Object],[object Object],[object Object]

REACTIONS OF ALKENES ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]

[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]

* Reaction with HCl needs a catalyst such as AlCl 3

MARKOVNIKOV’S RULE ,[object Object],[object Object]

[object Object],[object Object]

Step 2: Rapid reaction with a negative ion. The negative ion (Y - ) acts as nucleophile and attacks the positively charged carbon atom to give product of the addition reaction. Mechanism of electrophilic addition reactions: - C=C : electron rich part of the alkene molecule - Electrophiles: electron-seeking Step 1: Formation of carbocation. Attack of the pi bond on the electrophile to form carbocation. δ + δ -

ADDITION OF HYDROGEN HALIDES TO UNSYMMETRICAL ALKENES AND MARKOVNIKOV’S RULE

[object Object],[object Object],[object Object],[object Object]

[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],H +

[object Object],[object Object],H + = catalyst H +

[object Object],[object Object],[object Object],ANTI-MARKOVNIKOV’S RULE: FREE RADICAL ADDITION OF HYDROGEN BROMIDE

[object Object],[object Object],[object Object],[object Object],[object Object],OXIDATION

EPOXIDATION OF ALKENES ,[object Object],[object Object]

[object Object],[object Object],[object Object],[object Object],[object Object],HYDROXYLATION OF ALKENES glycol

* Also known as Baeyer’s test

[object Object],[object Object],[object Object],[object Object],OZONOLYSIS OF ALKENES

REACTIONS OF ALKENES WITH HOT, ACIDIFIED KMnO 4

[object Object],[object Object],[object Object],[object Object],POLYMERIZATION OF ALKENES

[object Object],[object Object],[object Object],[object Object],[object Object],UNSATURATION TESTS FOR ALKENES

[object Object],[object Object],[object Object]

[object Object],[object Object],DETERMINATION OF THE POSITION OF THE DOUBLE BOND

[object Object],[object Object],USES OF ALKENES

[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],POLYETHENE (PE)

POLYVINYL CHLORIDE (PVC) ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]

USES OF ETHANOL ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]

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Chapter 3 Alkenes