Organic Chemistry, Alkanes and Alkenes (Chapter 11, 12 and 13) Flashcards
What happens during the hydrogenation of alkenes if two double bonds are present?
Both double bonds are hydrogenated, so 2H2 is needed
Cis =
Z
How do photodegradable polymers decompose?
Carbonyl (C=O) bonds in the backbone of a polymer absorb light energy and break, fracturing the polymer chain
They are initially converted to waxy compounds when exposed to light, and then to carbon dioxide and water in the presence of bacteria
What is the equation for initiation?
Br — Br =(UV)= Br• + Br•
What is an alkene?
An unsaturated hydrocarbon containing a carbon-carbon double bond comprising a pi bond and a sigma bond
What happens during the first propagation step in radical substitution?
A bromine radical reacts with a C-H bond in the methane, forming a methyl radical (CH3•) and HBr
What is an elimination reaction?
The removal of a small molecule from a saturated compound to make an unsaturated compound
How does bond enthalpy affect the reactivity of the pi bond?
- A pi bond has a lower bond enthalpy than a sigma bond
- Therefore, the pi bond is weaker and is broken more easily
Why are radicals very reactive intermediates and what does this result in?
Because they have a single unpaired electron
This results in reactions occurring via a radical mechanism which is very difficult to control
What is an electrophile?
1) An electron pair acceptor
2) Atoms or groups of atoms that are attracted to an electron-rich centre and can accept an electron pair
3) They are always positively charged or partially positively charged
Via what does addition of a hydrogen halide to an unsymmetrical alkene form the major product?
The most stable carbocation
What is the molecular formula?
The number and type of each element present in a molecule e.g. C3H8O
What is the hydration of alkenes mainly used for?
To produce ethanol from ethene
How reactive are alkanes?
Not very - alkanes do not react with most common reagents
Explain carbocation stability
1) Each alkyl group donates and pushes electrons towards the positive charge of the carbocation (which is spread over the alkyl groups)
2) The more alkyl groups attached to the positively charged carbon atom, the more the charge is spread out, making the ion more stable
3) Therefore, the tertiary carbocation is more stable than the secondary, which is more stable than the primary
What do alkenes undergo addition reactions with?
Hydrogen ( + nickel catalyst)
Halogens
Hydrogen halides
Steam ( + acid catalyst)
What is the major product?
The more common product
The product formed from the secondary (or largest e.g tertiary etc) carbocation e.g. 2-bromopropane
What is the equation for the hydration of propene?
Propene + H2O (g) = propan-1-ol or propan-2-ol
Why is UV light needed for the reaction of alkanes and halogens?
The high-energy UV radiation present in sunlight provides the initial energy for a reaction to take place
Define aromatic
A compound containing a benzene ring
What are bioplastics?
They are made from plant starch, cellulose, plant oils and proteins
They offer a renewable and sustainable alternative to oil-based products
The use of them protects our environment and conserves valuable oil reserves
When the n is written in front of the monomer, what does it signify?
Many units of the monomer
What are compostable polymers?
Biodegradable polymers that degrade and leave no visible or toxic residues
Define aliphatic
A compound containing carbon and hydrogen joined together in straight chains, branched chains or non-aromatic rings
What is the ‘more highly substituted carbon atom’?
The carbon atom of the alkene with the greater number of hydrogen atoms and smaller number of carbon atoms
When do alkenes not obey their general formula?
When they are cyclic or polyunsaturated
How are photodegradable polymers made?
By blending the polymer with light-sensitive additives that catalyse the breakdown of the polymer
What is carbocation stability linked to?
The electron donating ability of alkyl groups
What is an alkane?
A saturated hydrocarbon containing single C–C and C–H bonds as σ-bonds
What is the minor product?
The less common product
The product formed from the primary carbocation e.g. 1-bromopropane
What is a sigma bond?
- A single covalent bond
- The overlap of orbitals directly between the bonding atoms
- It has free rotation
What happens during hydration reactions of alkenes?
Alkenes react with steam ( H2O (g) ) to form alcohols, in the presence of a phosphoric acid catalyst (H3PO4)
What is an example of a compostable polymer?
Poly(lactic acid) - it is being used in packaging and is made from corn starch (a renewable resource)
What are addition reactions of alkenes?
They involved the addition of a small molecule across the double bond, causing the pi bond to break and new bonds to form
Why is substitution at different positions in the carbon chain not a limitation for methane or ethane?
For methane, all four hydrogen atoms are bonded to the same carbon atom so only one monobromo compound, CH3Br is possible
Bromoethane could not have any structural isomers
When does heterolytic fission happen?
In a polar bond with an electronegativity difference
What is the skeletal formula?
The simplified organic formula, shown by removing hydrogen atoms from alkyl chains, leaving just a carbon skeleton and associated functional groups
- angle in C bonds = 109.5
- — = C1 - C2
What makes alkenes much more reactive than alkanes?
Because of the presence of the pi bond
What is electrophilic addition?
The mechanism for addition reactions to form saturated compounds
What is a monomer?
A small molecule that combines with many other monomers to form a polymer
What is cis isomerism?
When the hydrogen atoms on each carbon atom are on the same side of the double bond
What happens when polymers are recycled?
1) Discarded polymers have to be sorted by type
2) Once sorted, the polymers are chopped into flakes, washed, dried and melted
3) The recycled polymer is cut into pellets and used by manufacturers to make new products
What is an example of a biodegradable polymer?
Poly(glycolic acid) - it is being used in surgical stitches and is made from sugar cane and unripe grapes (renewable resources)
What is the displayed formula?
It shows the relative positioning (in 2D) of all the atoms and the bonds between them
What is a C=C double bond?
A sigma bond and a pi bond
What is trans isomerism?
When the hydrogen atoms on each carbon atom are diagonally opposite
What happens during the second propagation step in radical substitution?
Each methyl radical reacts with another bromine molecule, forming CH3Br and a new bromine radical
What are carbocations classified by?
The number of alkyl groups (represented by ‘-R’) attached to the positively charged carbon atom
What is Markownikoff’s rule?
When a hydrogen halide reacts with an unsymmetrical alkene, the hydrogen of the hydrogen halide attaches itself to the more highly substituted carbon atom
Define hydrocarbon
A compound containing hydrogen and carbon only
Where is the positive charge on the primary carbocation?
On a carbon atom at the end of a chain
How does a pi bond form?
A pi bond is formed by the sideways overlap of 2p orbitals on adjacent carbons, with electron density concentrated above and below the plane of the carbon sigma bond
Why are alkanes used as fuels?
Because they are readily available, easy to transport and don’t release toxic products during complete combustion
What is a reaction mechanism?
It tells us what is happening to the bonding electrons during a chemical reaction
What is the problem of disposing PVC?
Dumping PVC in a landfill is not sustainable
PVC releases HCl(g) (a corrosive gas) and other pollutants such as toxic dioxins when burnt
Why is CO harmful?
CO is a colourless and odourless toxic gas which combines irreversibly with haemoglobin, preventing it from transporting O2 around the body
Explain why subsitution at diferent positions in the carbon chain is a limitation of radical substitution
If the carbon chain is long enough (e.g. pentane), there will be a mixture of monosubstituted isomers
What kind of reaction is the halogenation of alkanes?
A substitution reaction - a H atom in the alkane is substituted by a halogen atom
What reaction happens in the propagation stage of radical substitution?
The reaction propagates through 2 steps in a chain reaction
What happens in practice during propagation?
Propagation is terminated whenever 2 radicals collide
What are the two carbocations possible in the reaction between propene and a hydrogen halide?
Primary and secondary carbocation
What is the bond enthalpy of a sigma bond?
347 KJ/mol
When to alkanes react with the halogens and which halogens?
In the presence of sunlight (UV light), alkanes react with halogens (only Cl2 and Br2)
What is poly(propene) used in?
Children’s toys, packing crates and guttering
What is the equation for the first propagation step in radical substitution?
CH4 + Br• = •CH3 + HBr
What is a radical?
A species with an unpaired electron