Organic Chemistry Flashcards
organic chemistry
the chemistry of carbon
1C
meth
2C
eth
3C
prop
4C
but
5C
pent
6C
hex
7C
hept
8C
oct
9C
non
10C
dec
C bonds
4
N bonds
3
H bonds
1
O bonds
2
saturated compound
all the chemical bonds between carbons are single bonds
unsaturated compound
at least one of the carbon to carbon bonds is a double or triple bond
aliphatic compounds
contain open (straight or branched) chains of carbon atoms and closed rings of carbon with similar properties
aromatic compounds
contain at least one benzene ring
functional group
a group of atoms which are present in all members of any series, which determines
homologous series
a group of organic compounds with a common functional group and successive members of the series differ in size by CH2
structural isomerism
compounds with the same molecular formula but have differnt structural formula
mirror images
not isomers
molecules that can be easily straightened
not isomers
addition reactions
a molecule has extra atoms added without losing any of its own atoms
substitution reactions
atoms already on a molecule are substituted or replaced by different atoms
hydrocarbons
only has hydrogen and carbon
nomenclature
system of naming
longest chain for alkanes
just the longest carbon chain
longest chain for non alkanes
longest carbon chain containing the functional group
which way to number for alkanes
keep the carbons carrying a substituent as low as possible
which way to number non-alkanes
carbons in functional group kept as low as possible
2 of the same substituent
di
3 of the same substituent
tri
4 of the same substituent
tetra
order to list different substituents
alphabetical
eg. 4-chloro-3-ethyl-3-methylheptane
numbers separted from numbers with a
,
numbers separated from letters by
-
rule 5 for alkene and alkynes only
position of double or triple bond indicated by lower of 2 numbers eg. pent-2-ene
what is boiling point an indication of?
how difficult it is to separate molecules from each other
are hydrocarbons polar or non-polar
non-polar
solubility of hydrocarbons
don’t dissolve in non-polar solvents such as water but do in non-polar eg.cyclohexane
solubility rule
like dissolves like
boiling points of hydrocarbons
weak van der waal forces, low boiling points
Mr of hydrocarbons increases
greater the boiling point
small hydrocarbons at room temp
gases
large hydrocarbons at room temp
liquids
aldehydes and ketones contain what?
carbonyl group
carbonyl group
\
C = O
/
boiling points of aldehydes and ketones and why
higher than hydrocarbons , dipole dipole attraction vs van der waal
solubility of aldehydes and ketones and why
both soluble in water, both have polar ends which are attracted to water by hydrogen bonding
if the aldehydes and ketones have long C-H chains
the nonpolar ends become bigger and more important
large nonpolar end repels water more than the smaller polar end attracts the water so that the larger aldehydes and ketones are insoluble in water
functional group of alcohols
hydroxyl group
hydroxyl group
-O-H-
boiling points of alcohols and why
higher than comparable aldehydes and ketones because of hydrogen bonding
comparable
same Mr
solubility of alcohols and why
very soluble in water, hydrogen bonding
alcohols with large C-H chains
C-H becomes the bigger part, overall molecule gets bigger and non-polar part is now more important than polar. dissolves in cyclohexane and not water
carboxylic acids functional group
carboxylic group
carboxylic group
O // - C \ O - H
boiling points of carboxylic acids and why
highest of all, hydrogen bonding and more sites for hydrogen bonding
summary of boiling points
Carboxylic acids, alcohols, aldehydes and ketones, hydrocarbons (alkanes, alkenes, alkynes)
double H bond, h bond, dipole dipole, van der waal
solubility of carboxylic acids and why
very soluble in water because they undergo hydrogen bonding
when C-H chain gets too long in carboxylic acids
non-polar part more important, dissolves in cyclohexane not water
crude oil
mixture of substances of different Mr
what is refining about
separating the substances from each other
fractional distillation
the heating of crude oil and then separating the various mixtures on the basis of their different boiling points
crude oil is
viscous
crude oil first goes into
a furnace
what goes in the bottom of the steel column
super heated steam
what comes out the bottom of the steel column
residue of tar
what happens in the furnace
it is partially vapourised
bottom of steel column
very hot
top of steel column
coolest part
interior of steel column arranged
in horizontal trays
X’s tray
X can be removed
above X tray
X is liquid and falls down
below X tray
X is gas under pressure and floats up
4 types of petroleum gas
methane
ethane
propane
butane
-CH3
methyl
-C2H5
ethyl
-C3H7
propyl
-C4H9
butyl
2 uses of petroleum gas
domestic bottle gas and LPG
LPG
liquid petroleum gas used in some cars
light gasoline aka
petrol
carbon atoms per molecule of petrol
5-10
use of petrol
for fuel
petrol is mostly
alkanes
carbon atoms per molecule of naptha
7-10
carbon atoms per molecule of something you can use to make petrol
5-10
2 uses of naphtha
petrol and raw materials
4 things naphtha is used as a raw material for
plastics, solvents, fibres, detergents etc
carbon atoms per molecule of kerosene
11-14
2 uses of kerosene
jet engine fuel
home heating
gas oil aka
diesel
carbon atoms per molecule of diesel
14-20
use of diesel
in diesel engines
carbon atoms per molecule of lubricating oil
20-30
use of lubricating oils
lubricating oil
lubricating oils are
viscous
why aren’t lubricating oils used as fuel
not easily vapourised
carbon atoms per molecule of fuel oil
30-35
use of fuel oil
can be made into droplets and used as ship and power station fuel
carbon atoms per molecule of bitumen
> 35
use of bitumen
road tar
smell of methane ethane etc.
odourless but sulphur containing mercaptans added to give a strong smells so leaks easily detected
smell of methane ethane etc.
odourless but sulphur containing mercaptans added to give a strong smells so leaks easily detected
petrol coming from fractioning column
inefficient fuel
what is an inefficient fuel
explodes on compression before spark ignites it
explodes on compression before spark ignites it
auto-ignition
auto-ignition causes
knocking
knocking causes 3
loss of power
engine damage
excessive noise in the car
what causes knocking
straight chain molecules
what prevents knocking
the presence of branched chain molecules
octane rating
the capacity of petrol to burn smoothly
octane rating scale
1-100
0 on octane rating
heptane
100 on octane rating
2,4,4 trimethylpentane
2,4,4 trimethylpentane aka
iso octane
definition of octane number of a fuel
the measure of the tendancy of a fuel to resist knocking
octane number of 97 efficiency
same as 97% 2,4,4 trimethylpentane and 3% heptane
2,4,4 trimethylpentane and heptane
reference substances
4 features of high octane rating fuel
- highly branched molecules
- short alkanes
- cyclical compound
- aromatic molecules
1 highly branched molecule
2,4,4 trimethylpentane
1 short alkane
pentane
1 cyclical compound
cyclohexane `
aromatic molecules
contain benzene
what was put into petrol before
anti-knocking agent
tetra ethyl lead
3 reasons why use of tetra ethyl lead was stopped
lead pollution in air
it’s tendency to poison catalytic convertors
toxicity to human health
4 ways to ensure petrol has a high octane number
isomerisation
reforming
adding oxygenates
catalytic cracking
isomerisation
when straight pentane and hexane with low octane numbers are heated and passed over a catalyst. they break up at and reform at random to give a mixture of straight and branched versions (isomers)
reforming aka
dehydrocyclisation
reforming
use of catalysts to form ring compounds, converted to cycloalkanes such as cyclohexane
2 things happening in reforming
hydrogen is expelled
aromatic compounds are formed
valuble hydrogen made in dehydrocyclisation
piped away
adding oxygenates
3 oxygen containing compunds added to petrol to increase it’s octane number
3 oxygen containing compunds that are added to petrol to increase it’s octane number
methanol
ethanol
MTBE
MTBE
methyl tertiary butyl ether
secondary use of oxygenates
reduce the level of pollutants coming from petrol, especially CO2 gas
catalytic cracking aka
cat cracking
cat cracking definition
the breaking down of long chain hydrocarbon molecules using heat and catalysts into smaller molecules which are more useful
cat cracking is carried out on… and why
kerosine, diesel oil and fuel oil, to obtain shorter molecules of carbon length 5-10 and higher octane rating
2 things cat cracking yields
more molecules with carbons lengths 5-10
smaller molecules such as alkenes
why are more molecules with carbons lengths 5-10 important
petrol can be manufactured
usually highly branched ie. high octane number
why are smaller molecules such as alkenes important?
manufacture of plastics and other chemical products
use of cracking allows chemists to…
use of cracking allows chemists to convert many of the fractions from crude oil for which there is little use
h2 burns readily in O2, what are products?
only H2O
H2 + 1/2 O2 ->
H2O
ΔH =
-242 kj/mole
3 difficulties with hydrogen as a fuel
expensive to produce
very explosive in air
very low density
how is hydrogen produced
electrolysis or steam reforming of methane
steam reforming of methane
burning of fossil fuels
why is very low density a problem
difficult to store
must be stored in high pressure containers
equation for steam reforming of methane to form H2
CH4 + H2O -> 3H2 +CO
equation for hydrogen gas being used in the industrial production of ammonia
N2 + 3H2 -> 2NH3
hydrogen also used in?
the hydrogenation of vegetable oils in margarine production
general formula of alkane
C2 H2n+2
functional group of alkanes
/ - C - / no double carbon bond no triple carbon bond no oxygen
name for alkanes
-ane
first alkane
methane
methane
CH4
ethane
c2H6
general formula of alkenes
CnH2n
functional group of alkenes
carbon to carbon double bond
first alkene
ethene
ethane
C2H4
general formula of alkynes
CnH2n-2
functional group of alkynes
carbon to carbon double bond
first alkyne
ethyne
ethyne
C2H2
alcohol general formula
CxHy-OH
functional group of alcohol
-O-H
first alcohol
methanol
methanol
CH3OH
general formula of aldehydes
CxHyCHO
functional group of aldehydes
O // -c \ H