4- Basics, Hydrocarbons, Alcohols, Haloalkanes, Analysis Flashcards
What is the stem name for one carbon
Meth-
What is the stem name for 2 carbons
Eth-
What is the stem name for 3 carbons
Prop-
What is the stem name for 4 carbons
But-
What is the stem name for 5 carbons
Pent-
What is the stem name for 6 carbons
Hex-
What is the stem name for7 carbons
Hept-
What is the stem name for 8 carbons
Oct -
Stem name for 10 carbons
Dec-
Display formula for butane
CH3CH2CH2CH3
What is the general formula
An algebraic formula that can describe any member of a family of compounds
What is the empirical formula
The simplest whole number ratio of atoms of each element in a compound
What is the molecular formula
The actual number of atoms of each element in a molecule
What is the structural formula
Shows the arrangement of atoms carbon by carbon with the attached hydrogens and functional groups
What is the skeletal formula
Shows the bonds of the carbon skeleton only, with any functional group. The hydrogen and carbon atoms aren’t shown.
What is the display formula
Shows all the atoms are arranged and all the bonds between them
What is a homologous series
An organic compound with the same functional group and similar chemical properties and general formula
Define hydrocarbon
A compound made of hydrogen and carbon atoms only
Define staurated
Has the maximum number of hydrogen atoms possible (around the carbon atom in a hydrocarbon)
Define unsaturated
An organic compound with a double / triple bond capable of adding subsitiuents through addition reactions
Define a functional group
An atom of group of atoms in an organic molecule, that determines its characteristic chemical and physical properties
What do consecutive members of a homologous series differ by
-CH2-
What is the general formula for alkanes.
CnH2n+2
Suffix for alkanes
-ane
Prefix of branched alkanes
Alkyl-
Suffix for alkanes
-ene
Prefix for haloalkanes
Chloro-
Bromo-
Iodo-
Suffix for alcohols
-ol
Suffix for aldehydes
-al
Suffix for ketones
-one
Prefix + suffix for cycloalkanez
Cyclo-….. -ane
Suffix for carboxylic acids
- oic acid
Prefix and suffix for esters
Alkyl-…..-anoate
All organic compounds contain a carbon skeleton - what are the 2 ways this can be
Aromatic or aliphatic
What do aromatic compounds contain
Benzene ring
What ao aliphatic compounds contain
Carbon, hydrogen
How are aliphatic compounds joined together
joined together in straight chains, branched chains or non-aromatic rings
If an aliphatic compound contain a (non aromatic) ring then it can be callled …..
Alicyclic
What are saturated compounds
Only contain carbon-carbon single bonds
What do unsaturated compounds have
Carbon -carbon double bonds, triple bonds or aromatic groups
What is an alkyl group
A fragment of a molecule
What is the general formula for an alkyl group
CnH2n+1
What does rhe main functional group of the molecule usually tell you….
What Homologous series the molecule is in, and gives the prefix or suffix
If there is more than one longest chain when naming organic compounds what do you do
Pick the one with the most side chains
What order do you put the prefix on IUPAC names
In alphabetical order, after the number of the carbon atom each is attached to
If there is more that one identical side chain or functional group. What do you use before that part of the name
2 (di-)
3( tri-)
4 (tetra-)
(Ignor these when factoring the alphabetical order)
When are two molecules isomers of one another
They have the same molecular formula but the atoms are arranged differently
What are the two types of isomers (organic)
Structural isomers
Stereoisomers
What is a structural isomer
The atoms are connected in differnt ways. So although the molecular formula is the same, the structural formula is differnt.
How many differnt types of structural isomers are there
3
What are the 3 types of structural isomers
Chain isomers
positional isomers
Functional group isomers
What is a chain isomer
The carbon skeleton can be arranged differnt, eg. A straight chain or branched in differnt ways
What are the properties like in chain isomers
Similar chemical properties but there physical properties like boiling points will be differnt because of the change in shape of the molecule
What is a positional isomer
The skeleton and rhe functional group could be the same, only with the functional group attached to a differnt carbon atom
Explain the properties in positional isomers
Differnt physicals properties
And the chemical properties might be differnt to
What are functional group isomers
The same atoms can be arranged into differnt functional groups
Explain the properties in functional group isomers
Very differnt physical and chemical properties
How many chain isomers are there with C3H7Br
0
How many positional isomers are there with C3H7Br
What are they
2 isomers
1-bromopropane
2-bromopropane
What are alkanes
saturated hydrocarbons
Every carbon atom has 4 single bonds with other atoms
What is the general formula for alkanes
CnH2n+2
What is the general formula for cyclo….ane
CnH2n
What is the shape of Alkane molecules around each carbon
Tetrahedral
What is the bond angle in alkanes
109.5
What are the boiling points like in alkanes
Smallest alkanes are gases at room temp and pressure as they have got a very low boiling point
larger alkanes are liquids they have a higher boiling points
Explain the difference in boiling points between small and large alkanes
1) alkanes have covalent bonds inside the molecules. Between the molecules there are induces dipole -dipole interactions (London forces) which hold them together
2) the longer the carbon chain,the strong the London forces. This is becuase there’s more surface contact and more electrons to interact with
3)as the molecule get longer it takes more energy to overcome the London forces and the booing points rise
Explain the differnce in boiling points between branches and unbranched alkanes
Branches chains Has a lower boiling points than its straight chain isomer. Branched chain alkanes can’t pack closely together and they have smaller molecular surface areas of contact. However straight chains can pack closely and there is a lot of surface contact between them so the London forces are reduced in branched chains.
If you oxidise (burn) alkanes with oxygen what do you get and what is the name of this reaction
Carbon dioxide and water
Combustion
Combustion equation
Alkane + oxygen = carbon dioxide + water
What do combustion reaction happen between
Gases
So liquid alkanes have to be varporised first
Smaller alkanes turn into gases ………. How else can this be described.
And what does that mean for how easy it will burn
More easy
(There more volatile)
it will burn more easily too
Larger alkanes release more energy per mole beacuse….
Because they have more bonds to react
Why are alkanes food fules
Lots of energy when they burn
All bases at the same temp and pressure have the same……
Molar ratio
How do you use the ratio of the volumes of the gases reaction together to calculate the molar ratio and therefore what hydrocarbon is combusting
1) using volumes provided, write the reaction equation
2) simplify
3) fill in the blanks with with you know. For example if 8 moles of o2 reacted to form 5 mole of carbon dioxide the rest of the mole must end as h20
4) use the final combustion equation to identity x
5) all the carbon atoms from x end up in carbon dioxide molecules and all the hydrogen most end as water
What does burning alkanes in limited oxygen produce
Carbon monoxide
Why is carbon monoxide poisonous
The oxygen in your blood stream is carried around by heamoglobim
Carbon monoxide is better at binding to haemonolobin than oxygen is so it binds to the heamoglobin in your blood stream before oxygen can
Thus means that less oxygen can be carried around your body leading to oxygen deprivation. At high concentrations, carbon monoxide can be fatal
What is an isomer
Molecules with the same molecular formula but differnt structural or spatial arrangementsof the atoms within the molecule
What are the 2 types of isomers
Structural
Sterioisomerism
What is a structural isomer
Same molecular formula but differnt structural formula
What is a position isomer
Molecule stays the same but the position of the functional group changes
Suffix for naming alcohols
Ol
When the alcohol group is not priority what is it called
Hydroxyl group
Where is the functional group on an aldehyde
Always on the terminal c atom ( so we don’t give a numerical position
Ketones suffix
-one
Suffix of haloalkanes
Ane
Alkenes suffering
Ene
What has the lowest priory when naming
Alkane and haloalkes
What has a higher priority in m,wind alchol or alkanes
Alcohol
When there is a alkene and a alcohol functional group how is it written
……… en ……- - ol
What has more priority a functional group or lowest numbers
Functional group
What are the two types of bond fissions
Homolytic
Heterolytic
What is bond fission
Breaking a covalent bond
What is heterolytic fission
In heterolytic fission the bond breaks unevenly with one of the bonded atoms recieving both electrons from the bonded pairs
Two differnt substances are formed - a positively charged cations and a negatively charged anion
What does a Curley arrow show
Movement of an electron pair
What is homolytic fission
The bond breaks evenly and each bonding atom recives one electron from the bonded pair. Two electrically charged ‘radicals’ are formed
What is a radical and how are they shown
A particle that have an unpaired electron
They are shown in mechanisms by a big dot next to the molecular formula (the dot represents the unpaired electron )
Are radicals reactive and why
Very
Because of the unpaired electrons
For which functional groups is it always on carbon 1
Aldehydes
Carboxylic acid
Nitriles
Does a high priority take the suffix or a prefix
Except form what
Suffix and lowest number
Double and triple c-c bonds only take suffic form
What is the order of the highest naming priority
Carboxylic acid > aldehydes > ketones > alcohols > alkenes > haloalkanes
If more than one double bond presents in an alkane , what happens to the name
DIene
TRI
And stem ends in a
What is the prefix for haloalkanes - fluorine
fluoro
What is the prefix for haloalkanes - chlorine
Chloro
What is the prefix for haloalkanes - bromine
Bromo
What is the prefix for haloalkanes - iodine
Iodo
When there are more than 2 OH groups
How does it change the name
Di or tri used
And an e on the stem name
If there is a alcohol and another functional group with a higher priority what is rhe alcohol called as a prefix
Hydroxy
What changed about the name when there are two aldehydes groups
Di
And an e is added to the stem.
What changes about the name when there are two ketones groups
Di
And an e is added to the stem
If there are Carboxylic acid groups on both ends of the chain
What is it called
Dioic acid
Halogens react with alkanes forming …….
Haloalkanes
Halogens react with alkanes in ………….. reactions
Photochemical
What are photochemical reactions starts by
Ultraviolet light
Describe a photochemical reaction
A hydrogen atom is substituted by chlorine or bromine
A hydrogen atom is substituted by chlorine or bromine
What’s is this reaction called
Free radical substitution
What is rhe 3 reaction mechanisms for free radical substitution with chlorine and methane
Initiation reaction
Propagation reactions
Termination reaction
What is initiation reaction
(With Chlorine and methane as an example )
Free radical substitution
1) sunlight provided enough energy. To break the cl-cl bond
This is photodissociation
Cl2 —-> 2cl.
2) the bonds splits equally and each atom gets to keep one electron x homolytic fission
The atoms becomes a highly reactive free radical becasue of its unpaired electron
What is it called when sunlight provids enough energy to break the cl-cl bond
Photodissociation
What is propagation reaction
(With Chlorine and methane as an example )
Free radical substitution
Free radicals are used to and created in a chain reaction
1) cl. Attacks a methane molecule : ch. + ch4 —> .ch3 + hcl
2) the new methyl free radical, , .ch3, can attack another cl2 molecule. : .CH3 + Cl2 —-> CH3Cl + Cl.
3) the new Cl. Can attack another ch4 molecule and so on until all the Cl2 or ch4 molecules are wiped out
What is a termination reaction
(With Chlorine and methane as an example )
Free radical substitution
1) the two free radicals join together, making a mole stable molecule,
2) there are heaps of possible termination reactions. Examples.
Cl. +.CH3 —> CH3CL
.CH3 + .CH3 —> C2H6
Cl. + Cl. —> cl2
What is a problem with free radical substitution
If your trying to make a particular product , you don’t get only the product your after but a mixture of products
General formula for alkenes
Cn H2n
What do au alkenes molecules have
At least one c=c double covalent bond
Are c= c double bonds unsaturated + why
Yes
Because they can make more double bonds with extra atoms in addition reactions
A double bund is made up of what two bonds
Sigma and pi
When is a sigma bond formed
When two s orbitals overlap
Explain what happens when two s orbitals overlap
- They overlap in a straight line.
This gives the highest possible electron density between two nuclei - this is a single covalent bond
The high electron density between the nucleus means there is a strong electrostatic attraction between the nuclei and the shared pair of electrons . This means that sigma bond have a high bond enthalpy
What is the strongest type of covalent bonds
Sigma bond
When is a pi bond formed
sideways overlap of two adjacent p orbitals
Whya have pi bonds got two parts to it
One above and one bellow the molecular axis. This is because the p orbitals which overlap are dumbbell shaped
Why are pi bonds weaker than sigma bonds
Because the electron density is spread out above and below the nuclei. This means that the electrostatic attraction. Between the nuclei and shared pair of electrons. Is weaker so pi bonds have a relatively low bond enthalpy
Are C-C and C-H sigma or pi bonds
Sigma
Why don’t alkanes react easily
Only contain C-C and C-H sigma bonds which have high bond enthalpy and so are difficult to break.
The bonds are non polar do they don’t attract nucleophiles or electrophiles
Why are alkenes more reactive
The C=C bonds contains both sigma and pi bond
The C=C double bond contains four electrons so it has a high electron density and the pi bond also sticks out above and below the rest of the molecule. These two factors means rhe pi bonds is likely to be attacked by electrophiles.
The low bond enthalpy of the pi bond also contributes to the reactivity .
Why are alkenes good starting points for making other organic compounds
Because the double bond is so reactive
What are alkenes good starting points for
Organic compounds and for making petrochemicals
can double bonds rotate
Yes
How are atoms arranged in a C=C double bond
1) Carbon atoms in a C=C double bond and the atoms bonded to these carbons all lie in the same plane (they’re planar).
Because of the way they’re arranged, they’re actually said to be trigonal planar — the atoms attached to each double-bonded carbon are at the corners of an imaginary equilateral triangle.
What are the bond angles in the planar unit
All 120°
Are all alkenes completely planar
In ethene yes
But not in larger alkenes
But the >C=C< unit is still planar
Why can’t C=C atoms around it rotate
Because of the way the p orbitals overlap to form a pi bond
Are double bonds rigid
Yes
Even though atoms can’t rotate about a double bonds, they can still rotate …..
About any single bond in a molecule
The restricted rotation around the C=C double bond is what causes alkenes to form, ……
Stereoisomers
What is a stereoisomers
Have the same structural formula but a differnt arrangement in shape
When do stereoisomers occur
When two double bonded carbon atoms each have two differnt atoms or groups attached to them
What are the names of the stereoisomers
Z-Isomer
E- isomer
What is a Z-isomer
Same group either both above or below the double bond
What is the E-isomer
The same group positioned across the double bond
How Is the E and Z separeated from the name when naming stereoisomers
By a dash
Who came up with the solution to the problem with stereoisomers having totally differnt groups attached
Mr cahn
Mr ingold
Mr prelog
What is the name for the rules used to work out which is E or Z isomers for any alkenes
Cahn-ingold-prolog (CIP) rules
How does CIP rule name E and Z isomers
Looks at the atoms directly bonded to each of the C=C carbon atoms
Atoms with the higher atomic number of each carbon is given the higher priority
You can now assign the isomers as E and Z.
if the 2higher priority groups are positioned across the double bond from one another is the E isomer
If a carbon is directly bonded to two carbon atoms, what do u do when looking if E or Z isomers
you need to go further along the chain to work out ordering
The methyl carbon is only attached to the hydrogen atom but ethyl carbon is attached to another carbon atom so the ethyl group is high priority
What can E/Z isomers also be known as
Cis - trans isomers
of the carbon atoms have at least one group in common then you can call the isomers what …..
Cis or trans
Or
E- or Z-
What does cis means for naming stereoisomerism
The same groups are on the same side of the double bond
What does trans mean in naming stereoisomers
the same groups are on opposite side of the double bond
When does the cis - trans system not work
If the carbon atoms both have totally differnt groups attached to the,
What is an optical isomer
A special kind of stereoisomerism that occurd when there is an asymmetrical carbon with an organic molecule - called a chiral carbon
WHat is a chiral carbon
Carbon with 4 different substituents bonded to the centre carbon atom - so no line of symmetry
Asymmetrical molecules arise due to the chiral carbon what does it give rise to
Two isomers (non-superimposable mirror images)
They are optical isomers
What are the two optical isomers known as
Enatiomers of each other
(Oftern with a + or - depending on how they effect the plan of polarised light)
Each enatiomer of a chiral molecule will rotate the plan of polarises light by …..
90°
+ enantimer - rotates the plane by 90°………..
Clockwise
-enantimer - rotates the plane by 90°………..
Anti-clockwise
If a 50:50 enantiomer split what is it called
Racemic
Aliphatic
Carbon atoms are joined to each other in branched or unbranched chains or non aromatic rings
Alicyclic
Carbon atoms are joined to each other in ring structures
Aromatic
Some or all the atoms are joined in a benzene ring
What is the bonding in alkanes
Bond is the result of the overlap between two orbitals of the bonding atoms ( sigma bonds)
Each carbon atoms have 4 sigma binds
What is the shape of alkanes and the bong angle
Tetrahedral
109.5 °
Why are alkane shapes flexible
The sigma bond lie between the two atoms in a horizontal plane and there is free rotation
Describe of a sigma bond in alkanes
One SP3 orbital form each carbon overlap to form a single c-c bond called a sigma bong
What is this called
1S2 2S2 2p2 ——-> 1s2 2s1 2p3
Hybridisation
How does boiling point change as the carbon chain increases in alkanes
Increases
Why does boiling point increase as chain length of alkanes increase
As chain length increases the molecule will have a larger surface area
This is greater constant between molecules
London forces between molecules are therefore greater
How does branching of alkanes effect boiling points
Branched chain compounds have lower boiling points than the corresponding straight chain isomer
The London forces depend on the surface area of contract, it becomes smaller on account of branching so the boiling point of the branched chain alkenes are less than the straight chain isomers
Are alkanes soluble in non polar substances and why
Yes
They are non polar
They interact and from new London forces overcoming the old ones
Are alkanes soluble in polar solvents and why
No
They are non polar
A lot of energy is required to overcome the hydrogen bonding in water, any interaction of alkane and water will only result in new London forces + this is not energetically equivalent to overcoming the old London forces and hydrogen bonding
What are electrophilic addition reactions
The alkene double bond opens up and atoms are added to the carbon atom
Why do electrophilic addition reactions happen
The double bond has got plenty of electrons and is easily attacked by electrophiles
What are electrophiles
Electron pair acceptors
They are usually shot of electrons so they’re attracted to areas where there are lots of electrons
Give some examples of electrophiles
Positive charged ions
Like H+
And polar molecules
What does adding hydrogen to C=C bond produce
Alkanes
What are the conditions for addinf hydrogen to a C=C double bond to produce an alkane
(Hydrogenation )
Nickel catalyst
150°c
Halogens react with Alkenes to form what
Dihaloalkanes
Describe halogenation
The halogen is added across the double bond. And each of the carbon atoms end up bonded to one halogen atom
What type of reaction is halogenation
Electrophilic addition
Describe the mechanism of halogenation
With bromine and ethene as an example
( how would this be differnt for H-Br)
The double bond repels the electrons in br2 polarising Br-br
Heterolytic fission of Br2. The closer Br gives up the bonding electron to the other br and bonds to the C atom
You get a positively charged carbocation intermediate. The Br- now goes over and bonds to the other c atoms forming 1,2-dibromoethane
H-br aleardy has a permanent dipole so step one isn’t necessary
How can u test for carbon carbon double bonds
Add bromine water
Shake
Colour changes orange to colourless
Why does adding bromine water to an alkene decolourise
Becuase bromine is added across the double bond to form a colourless dibromoalkane
Alkenes can be hydrated by steam to form what
Alcohols
What is the reaction from Alkenes to alcohol called
Hydration
What conditions are needed for hydration reaction
300°c
Pressure 60-70 atm
Solid phosphoric (v)acid catalyst
Is the hydration reaction of Alkenes to Alcohols reversible and what is the reaction yield like
Yes
Low (It’s only around 5% from ethene but u reacted alkene gas can be recycled and up ethene yield to around 95%)
Alkenes undergo addition reactions with hydrogen haldies to form what
Haloalkanes
If hydrogen halides add to an unsymmetrical alkene how many possible products are there
And what does rhe amount of each product depend on
2
How stable the carbocation formed in the middle of reaction is
Are carbocations with more alkyls groups more or less stable and why
More because the alkyl group feeds electrons towards the positive charge. So the more stable carbocations is more likely to form
What is a primary/secondary/tertiray carbocation
Refers the the number of r groups
Primary = 1 r groups
Tertiray = 3 r groups
Order primary , secondary and tertiray carbocations into leats to most stable
Primary
Secondary
Tertiray
How does hydrogen bromine react with propene
1) the secondary carbocation is more stable because it’s got two alkyl groups
This carbocation forms more of the time
2) the primary carbocation is less stable as its only got one alkyl group it forms less oftern
What is rhe markownikoff rule
The major product form addition of a hydrogen halide (HX) to an unsymmetrical alkene is the one where hydrogen adds to the carbon with the most hydrogen already attached
Describe complete combustion
Plentiful supply of O2
Alkanes burn completely
Products = co2 and H2O
Products of complete combustion
CO2 and H2O
Describe incomplete combustion
Limited supply if O2
Less energy released per mole than complete
Leads to C or CO
What are the products of incomplete combustion
C or CO
And water
Why are alkanes good fules
Readily available
Easy to transport
Burn in plentiful supply of O2 without producing toxic products
Highly exothermic when combusted
What are the harms of CO
Highly toxic
Odourless
causes death if accumulated in an enclosed space
Toxic to humans
Why is carbon monoxide toxic to humans
Binds with haemoglobin in RBC to from carboxyhaemoglobin ( a stronger bond than that between oxygen and haemoglobin)
Symptoms of carbon monoxide poisoning
Tension headaches
Dizziness
Nausea
Vomiting
Tiredness
Confusion
Stomach pain
Difficulty breathing
What does rhe % level of carboxyhaemoglobin have to be to indicate severe exposure to carbon monoxide
30%
Treatments of carbon monoxide
Breathing in conc O2 and hyperbaric oxygen therapy
What is another word for carbon
Soot
Why is carbon not a desirable product
Global dimming - carbon particles reflect sunlight back into space
Health - soot can enter body (leads to breathing issues)