Chapter 13 - Alkenes Flashcards
What is the general formula of an alkene?
CnH2n
What is a pi bond?
The sideways overlap of 2 p orbitals, one from each carbon atom of the double bond - each C atom contributes one electron to the electron pair in the pi bond.
How does a pi bond affect the geometry of an alkene?
The pi bond locks the two C atoms in position, preventing them from rotating around the double bond
What is the shape and bond angle around a double bond, and why?
Trigonal planar, 120 degrees
Due to 3 regions of electron density around each carbon atom, which repel as far as possible
What is a stereoisomer?
Structures with the same molecular formula, but with a different arrangement of the atoms in space
Why is there stereoisomerism around a double bond?
Because rotation around the double bond is restricted and the groups attached to each carbon atom are therefore fixed relative to each other
What conditions must a molecule satisfy to demonstrate E/Z isomerism?
- a C=C double bond
- different groups attached to each carbon atom of the double bond
What is the difference between cis-trans isomerism and E/Z isomerism?
Cis-trans isomers must have one of the attached groups on each carbon atoms as the same
How do you decide if a molecule is a Z or E isomer?
If groups of higher priority are on same side of double bond, the compound is Z isomer
If groups of higher priority are diagonally placed across the double bond, the compound is E isomer
How do you assign priority to the substituent groups for E/Z isomerism?
The higher the atomic number, the higher the priority.
If the two atoms attached to a carbon atom in the double bond are the same, you have to find the first point off difference - whichever has higher atomic number is higher priority
Why are alkenes more reactive than alkanes?
Due to their pi bond - which more readily breaks as the electrons are more exposed than the electrons in a sigma bond. It is easier to break pi bond than sigma bond
What are the conditions required when alkenes undergo hydrogenation, and what products are formed?
Conditions: nickel catalyst, 423K
Addition reaction forms alkane as hydrogen added across double bond
What are the conditions required when alkenes undergo halogenation, and what products are formed?
Conditions: room temp
Forms haloalkane as double bond opens up for diatomic halogen molecule
How can bromine water be used to test for unsaturation?
Bromine adds across the C=C double bond in alkenes and bromine water (usually orange) decolourises.
What are the conditions required when alkenes undergo addition with hydogen halides, and what products are formed?
Conditions: room temperature
Forms haloalkanes