Module 4 Section 1: Basic Concepts and Hydrocarbons Flashcards
All the formula types and what they show
General formula - algebraic formula that describes any member or family of compound
Empirical - the simplest ratio of atoms of each element in a compound (cancel numbers down if possible)
Molecular - actual number of atoms of each element in a molecule
Structural - shows atoms carbon by carbon, with the attached hydrogens and functional groups (structure of each section)
Displayed - shows how all the atoms are arranged and all the bonds between them (like ball and stick model)
Skeletal - shows the bonds of carbon skeleton only, with any functional groups. The hydrogen and carbon atoms aren’t shown (zig zag, handy for drawing large complicated structures)
all the formulas for butan - 1 - ol
General: CnH(2n+1)OH
Empirical: C4H10O ( ethane, C2H6, is CH3
Molecular: C4H10O
Structural: CH3,CH2,CH2,CH2,OH or CH3(CH2)3OH
Displayed: ball and stick type ( moly mod )
Skeletal: \ /\ /OH
What is a homologous series
A group of compounds that have the same functional group and general formula
Consecutive (/successive) members of a homologous series differ by -CH2
What is the simplest homologous series called
Simplest is the alkanes
These are straight chain molecules that contain carbon and hydrogen atoms only
General formula for alkanes
CnH(2n+2)
What are the first 10 alkanes
1 carbon atom: methane CH4
2 carbon atoms: ethane C2H6
3 carbon atoms: propane C3H8
4 carbon atoms: butane C4H10
5 carbon atoms: pentane C5H12
6 carbon atoms: hexane C6H14
7 carbon atoms: heptane C7H16
8 carbon atoms: octane C8H18
9 carbon atoms: nonane C9H20
10 carbon atoms: decane C10H22
How to name any organic compound
1) Count the carbon atoms in the longest continuous chain which gives you the stem
2) The main functional group of the molecule usually gives you the end of the name
3) Number the longest carbon chain so that the main functional group has the lowest possible number, if there’s more than one longest chain, pick the one with the most side chains
4) Any side chains or less important functional groups are added as prefixes at the start of the name, put them in alphabetical order with the number of the carbon atom each it attached to
5) If there is more than one identical side chain of functional group, use di- (2), tri- (3) or tetra- (4) before that part of the name - but ignore this when working in alphabetical order
Prefix, suffix and example for alkanes
Prefix or suffix: -ane
E.g. propane
Prefix, suffix and example for branched alkanes
Prefix or suffix: alkyl-, -yl
E.g. methyl propane
Prefix, suffix and example for alkenes
Prefix, suffix: -ene
E.g. propene
Prefix, suffix and example for haloalkanes
Prefix, suffix: chloro-, bromo-, iodo-, ( no suffix )
Chloroethane
Prefix, suffix and example for alcohols
Prefix, suffix: hydroxy-, -ol
E.g. ethanol
Prefix, suffix and example for aldehydes
Prefix, suffix: oxo-, -al
E.g. ethanal
Prefix, suffix and example for ketones
Prefix, suffix: oxo-, -one
E.g. propanone
Prefix, suffix and example for cycloalkanes
Prefix, suffix: cyclo-, -ane
E.g. cyclohexane
Prefix, suffix and example for Arenes
Prefix, suffix: benzene
E.g. ethylbenzene
Prefix, suffix and example for esters
Prefix, suffix: oxycarbonyl-, -alkyl, -anoate
E.g. propyl ethanoate
Prefix, suffix and example for Carboxylic acid
Prefix, suffix: Carboxy-, -oic acid
E.g. ethanoic acid
Difference between aromatic and aliphatic compounds
Aromatic compounds contain a benzene ring
Aliphatic compounds contain carbon and hydrogen joined together in straight chains, branched chains or non - aromatic chains
If an aliphatic compound contains a ( non - aromatic ) ring, then it can be called alicyclic
Difference between saturated and unsaturated compounds
Saturated compounds only contain carbon - carbon single bonds - like alkanes
Unsaturated compounds can have carbon - carbon double bonds, triple bonds or aromatic groups
What is an alkyl group
An alkyl group is a fragment of a molecule with general formula CnH2n+1
( looks like a bit of an alkane attached to the side of the chain )
What are isomers and what are the two we need to know
Two molecules are isomers of one another if they have the same molecular formula but the atoms are arranged differently
The two isomers we need to know are structural isomers and stereoisomers
Structural isomers and the 3 types
In structural isomers, the atoms are connected in different ways
Although the molecular formula is the same, the structural formula is different
3 types include: chain isomers, positional isomers and functional group isomers
Chain isomers and examples
The carbon skeleton can be arranged differently - e.g. as a straight chain, or branched in different ways
These isomers have similar chemical properties
But their physical properties, like boiling point , will be different because of the change in shape of the molecule
E.g. butane and methylpropane are chain isomers of eachother
Positional isomers and examples
The skeleton and the functional group could be the same, only with the functional group attached to a different carbon atom
These also have different physical properties, and the chemical properties might be different too
E.g butan - 1 -ol and butan - 2 - ol
Functional group isomers and examples
The same atoms can be arranged into different functional groups
These can have very different chemical properties
E.g. butanoic acid and methyl propanoate
Prefix, suffix and example for acid halide
Prefix/ suffix: halocarbonyl-, -oyl halide
e.g. ethanoyl chloride
Prefix, suffix and example for amides
Prefix/ suffix: carbamoyl-, -amide
e.g. methanamide
Prefix, suffix and example for nitrile
Prefix/ suffix: cyano-, -nitrile
e.g. propanenitrile
Prefix, suffix and example for thiol
Prefix/ suffix: sulfanyl-, -thiol
e.g. propanethiol
Prefix, suffix and example for amine
Prefix/ suffix: amino-, -amine
e.g. ethylamine
Prefix, suffix and example for sulfide
Prefix/ suffix: (no prefix), -sulfanyl (so this is for when secondary)
e.g. hexanethiol
Prefix, suffix and example for ether
Prefix/ suffix: (no prefix), -oxy-
e.g. methoxybutane
What is a functional group?
A group of atoms in a molecule responsible for the characteristic reactions of the compound
What is the functional group priority list
Carboxylic acid
Ester
Acid halide
Amide
Nitrile
Aldehyde
Ketone
Alcohol
Thiol
Amine
Imine
Ether
Sulfide
Alkene
Alkyne
Haloalkane
Nitro
What is heterolytic fission
The bond breaks unevenly with one of the bonded atoms receiving both electrons from the bonded pair
Two different substances are formed - a positively charged cation ( X+ ), and a negatively charged anion ( Y- )
What is homolytic fission
The bond breaks evenly and each bonding atom receives one electron from the bonded pair
Two electrically uncharged radicals are formed
What are radicals
Particles that have an unpaired electron
They are shown in mechanisms by a big dot next to the molecular formula
Radicals are very reactive due to the unpaired electron
How do halogens react with alkanes
Halogens react with alkanes in photochemical reactions
These are started by light - this requires ultraviolet light to start
A hydrogen atom is substituted by chlorine or bromine
This is a free radical substitution reaction
E.g. CH4 + Cl2 —UV—> CH3Cl + HCl
What are the three stages of reaction mechanism
Initiation reactions
Propagation reactions
Termination reactions
What happens in initiation reactions
Free radicals are produced by homolytic fission
UV provides energy to break Cl-Cl bond - this is photodissociation: Cl2 —UV-> 2Cl
The atom becomes a highly reactive free radical, Cl •, because of its unpaired electron
What happens in propagation reactions
Free radicals are used up and created in a chain reaction
Cl • attacks a methane molecule: Cl • + CH4 -> •CH3 + HCl
The new methyl free radical, •CH3, can attack another Cl2 molecule: •CH3 + Cl2 -> CH3Cl + Cl •
The new Cl • can attack another CH4 molecule, and so on, uncial all the Cl2 or CH4 molecules are gone
What happens in termination reactions
Free radicals are mopped up
If two free radicals join together, they make a stable molecule
There are lots of possible termination reactions
E.g.
Cl • + •CH3 -> CH3Cl
•CH3 + •CH3 -> C2H6
What’s the problem with free radical substitution
You do not always get the desired product, instead you get a mixture of products
E.g. if you’re trying to make chloromethane and there’s too much chlorine in the reaction mixture, some of the remaining hydrogen atoms on the chloromethane molecules will be swapped for chlorine atoms
The propagation reactions happens again to make dichloromethane, again to make trichloromethane and again to make tetrachloromethane
Also, it can take place at any point along the carbon chain
So a mixture of isomers can be formed e.g. reacting propane with chlorine will produce a mixture of 1-chloropropane and 2-chloropropane
How to reduce the problems with free radical substitution
Have an excess of methane so there’s a greater chance of a chlorine radical colliding only with a methane molecule and not a chloromethane molecule
What are alkenes and what is their structure
Unsaturated compounds with the general formula CnH2n
They are hydrocarbons as they are made of carbon and hydrogen atoms only
Alkenes all have at least one C=C double covalent bond
C=C double bonds make the molecule unsaturated as they can make more bonds with extra atoms in addition reactions
What is a σ bond and when is it formed
σ bond ( sigma bond ) is formed by two s orbitals direct overlap
The two s orbitals overlap in a straight line - gives the highest possible electron density between the two nuclei
This is is a single covalent bond
The high electron density between the nuclei means there is a strong electrostatic attraction between the nuclei and the shared pair of electrons
This means σ bonds have a high bond enthalpy - strongest type of covalent bonds
What are π bonds
π ( pi ) bonds are formed by sideways overlap of two adjacent p orbitals
It’s got two parts: one above and below the molecular axis
This is because the p orbitals which overlap are dumb bell shaped
π bonds are much weaker than σ bonds as the electron density is spread out above and below the nuclei
This means the electrostatic attraction between the nuclei and the shared pair of electrons is weaker, so π bonds have relatively low bond enthalpy