Alkenes Flashcards
WHOLE lot more to learn, so treat it royal :D
What are alkenes?
- Unsaturated hydrocarbonds!
- Can be Branched, Cyclic and Linear!
What is a π - bond?
- Where 2 P-Orbitals sideways overlap, with e- density ABOVE AND BELOW line joining BOTH C atoms
- Always occurs where C=C takes place!
Difference with σ-bond and π-bond?
- Pi = 2 regions of e- density ABOVE AND BELOW line - weaker than sigma bond, 2 p orbitals overlaping
Sigma = everything of opposite!
How can we describe the C=C bond in detail?
- Bonding around carbon with 3 sigma, 1 pi bond (always!!!) = 3 REGIONS OF e- DENSITY!
- 3 bonding regions, 0 lone pairs = 120’
- pi bond locks 2 carbons in position, preventing ROTATION AROUND C=C BOND!
What gives C=C bond its strict rigidity?
- Due to pi-bonds e- density position ABOVE AND BELOW plane of sigma-bond!
- will mean that groups attached per carbon will be fixed, relative to each other!
What is Stereoisomersim?
Where same structural formula, different arrangement in space!
What is E/Z Isomerism?
- This is when different groups attached to each carbon in C=C has different arrangement in space, restricted due to no rotations!
italics = both conditions needed to be met!
What makes an E and Z isomer?
- E = group in common will be on opposite sides of molecule, mirroring position in space!
- Z = group in common will be on the same side of molecule in space!
ZAME side on the SAME side!
Difference with Cis-Trans and E/Z Isomerism
- CIS-TRANS = Special case of E/Z isomerism, where carbons in C=C must still have differing groups, but 1 OF THE GROUPS MUST BE THE SAME IN BOTH CARBONS!
- TRANS = same group attached to C=C on opposite side of molecule! = TRANS = E
Hence, ALL cis-trans are a type of E/Z, but not vice versa
What is Cahn-Ingold-Prelog nomenclature?
- Atoms attached per carbon atom in C=C are given PRIORITY BASED ON ATOMIC NUMBER
- Groups of higher priority on same side = Z isomer
What to do with Cahn-Ingold-Prelog when with complex groups?
- we have to observe the FIRST POINT OF DIFFERENCE on the complex groups!
- if this point has higher atomic number, higher priority is then assigned!
Why are alkenes more reactive than alkanes?
- Due to pi-bond precense, meaning high e- density outside of C=C
- Greater exposure, with weaker pi-bonds = less energy required to break, and donate electrons…
How does Hydrogenation and Halogenation work?
- HYDRO: Hydrogen gas + nickel catalyst, at very high tempratures (removing double bond»_space; alkane)
- HALO: Halogen gas reacted under room temprature, rapidly, (removing double bond via ADDITION»_space; alkane)
How does Hydration and Bromine Test work?
- HYDRATE: Alkene + H2O under phosphoric acid catalyst presence, gives extra H and OH group = ALCOHOL!
- BT: Identifying presence of C=C bond, being unsaturated, Orange-Brown>Colourless
Mechanism for Electrophilic Addition?
- Halogen Halide/Halogen as polar/iunduced molecule has gained e- pair from alkene C=C, while undergoing heterolctic fission
- Carbocation formed, anion gained e- pair, and bonds to carbocation
- New molecule formed! (all shown via CURLY ARROWS!!!!!!)
What is Markownikoff’s Rule?
- This describes when a halogen halide reacts with an asymmetrical alkene, the hydrogen atom will attach itself to the carbon atom with the most hydrogen atoms!
TO REMEMBER: “The rich get richer”, carbon with most H = richest!
Describe carbocation stability!
- The more hydrogen atoms present on C, the LOWER THE STABILITY
- LOWER STABILITY = GREATER CHANCE FOR HALIDE TO ATTACH TO C OF CARBOCATION (+)
- Hence, primary>secondary>tertaity carbocation is order!
- Order due to more alkyl groups present, the greater the spread of positive charge via carbocation, meaning greater stability
How to draw 2,3,4 ect repeating monomers?
- Draw the monomers joined together, with a line continuing from both ends (n not even needed)
Environmental concerns for POLYMERSSSSS WASTE!
- Incinerating for energy source (but PVC will release HCL into air if burnt = toxic)
- Feedstock recyclying, suitable for unsorted + unwashed polymers, products used as raw material in manufacure of new polymers
- Biodegradeable/photodegradeable polymers, natural breakdownvia microorganisms!