Alkenes Flashcards
What do curly arrows represent?
The movement of electrons
What does the double bond of alkenes have?
A high electron density
What happens due to the high electron density of carbon carbon double bonds in alkenes?
Makes the bond more susceptible to attack by electrophiles
What are electrophiles?
Electron loving species
What is electrophilic addition?
The addition of an electrophile to a double bond
What does electrophilic addition include?
Hydrogen (hydrogenation reaction)
Steam
Hydrogen halide
Halogens
Which catalyst does hydrogenation use and what does it produce?
A nickel or platinum catalyst and it produces an alkane
Occurs under heat
What catalyst does reaction with steam use and what does it produce?
Phosphoric acid catalyst and it produces an alcohol
Occurs under heat
What do electrophilic additions with hydrogen halides and halogens produce and what conditions do they occur under?
Halogenoalkanes
Happens at room temperature
What is hydrogenisation extensively used for in industry?
To manufacture margarine
How is margarine produced?
- Naturally occurring vegetable oils are unsaturated
- Reacted with H2 and become C-C
- Process changes properties of vegetable oils and converts it to solid
What can alkenes be oxidised and acidified by?
Potassium Manganate (VII) (KMnO4) - very powerful oxidising agent
What happens when alkenes are shaken with cold, dilute KMnO4)?
Pale purple solution turns colourless and product is a diol ( colour change can be used to distinguish between alkenes and alkanes as alkanes don’t change colour)
How can we think of the reaction between an alkene and an oxidising agent?
As an oxidation reaction followed by an addition
What are the steps in reacting an alkene with oxidising agent?
- Potassium manganate solution provides an oxygen atom
- Water in solution provides another oxygen and 2 hydrogen atoms, so addition of 2 OH groups across the double bond
What is heterolytic fission?
Breaking a covalent bond so that the more electronegative atom takes both the electrons from the bond to form a negative ion and leave behind a positive ion
What is the charge of hydrogen halides?
They are polar
e.g. HBr = H is positive, Br is negative
Which atom in HBr would be the electrophile?
H as it is electron deficient
What happens in an addition reaction of an alkene and a hydrogen halide?
The H atom acts as an electrophile and accepts a pair of electrons from the C=C in the alkene
What happens to the H-Br bond during electrophilic addition?
Breaks heterolytically, forming a Br- ion
What happens after the H has received the electron pair from the C=C in electrophilic addition?
Results in formation of a highly reactive carbocation intermediate which reacts with the Br- (nucleophile), to form halogenoalkanes
What is the charge of halogen molecules?
Non-polar
What happens when a Br molecule gets closer to the double bond of an alkene?
The high electron density in the double bond repels the electron pair in the Br-Br away from the closest Br atom
What happens in terms of charge on each Br atom as it gets closer to the C=C in an alkene?
Br closest becomes an electrophile and Br furthest away gets a negative charge (there is an induced dipole)