Organic Chemistry Flashcards
what are hydrocarbons?
molecules composed mainly of carbon and hydrogen atoms.
how many bonds does carbon form?
4
tetrahedral arrangement
109.5 degrees apart from each other
homologous series
a group of compounds that have the same general formula or have a unique functional group.
what are the defining features of alkanes?
- single C-C bonds
- saturated because the backbone is completely surrounded by carbons
- CnH2n+1
9
non
10
dec
11
undec
12
dodec
properties of alkanes
- shorter have lower BP because of less intermolecular bonds, less energy is needed to overcome them
- at room temp: ethane, propane and butane are gases
- larger are liquids and some are solids
- insoluble in water
- soluble in organic solvents
- shorter are more volatile (evaporate easily), increasing flash point (easier to combust)
- larger alkanes are more viscous
viscosity
depends on the interaction between molecules. Increased length, means increased strength of dispersion forces and thus viscosity increases.
alkyl groups
refers to branching from the backbone
isomer
chemical substances that have the same chemical formula but different structural formulas
what effect does branching have on chemical properties?
increased branching, decreased surface area and hence a decrease in intermolecular bonding, so a decreased BP
what are the features of alkenes?
- double C-C bond
- unsaturated because carbon backbone is not completely surrounded
- CnH2n
is a double bond a functional group?
yes
naming alkenes
- determine longest chain
- number the carbons closest to double bond and give the bond a number
properties of alkenes
- smaller have lower bP
- ethene, propene and butene are gases at room temp
- larger are liquids or solids (more than 16C)
- insoluble in water
- soluble in organic solvents
- C-C double bond makes the, highly reactive
what reactions can alkanes participate in?
- combustion
- substitution
what is a substitution reaction?
an atom or a functional group is swapped by another atom or group of atoms
what products are them of a substitution reaction?
the new hydrocarbon and the atoms removed that form a small molecule
what can alkanes form in substitution reactions?
halogenated hydrocarbons, amines, alcohols
important consideration in substitution reactions?
only saw one hydrogen atom at a time for a new atom or group of atoms
if a reaction occurs between an alkane and an excess of a new atom (eg. Cl2), a series of substitution reactions can occur
halogens in halogenated hydrocarbons
- only need one electron and are thus highly reactive and electronegative
- hydrogen is swapped for one
naming a halogenated hydrocarbon
- longest chain
- identify location of functional group
- use numbers to show position
- functional groups with functional groups in alpha order
what are amines? how are they formed?
- amino functional groups that have a nitrogen attached to two hydrogen atoms
- polar due to hydrogen bond
- can be produced by a substitution reaction where a hydrocarbon reacts with ammonia (NH3)
primary amines
C atom attached to NH2 is attached to one other alkyl group
secondary amines
C atom attached to NH2 is attached to two other alkyl groups
tertiary amines
C atom attached to NH2 is attached to three other alkyl groups
nomenclature priority
most: carboxylic acid, ester, aldehyde, ketone, alcohol, amine, alkyne, alkene, alkane: least
how is an amine named when amine is priority?
becomes suffer -amine eg. propylamine
how is an amine named when amine is not priority?
amino - propanol
why are amines polar? what does this mean?
- asymmetrical
- can hydrogen bond with water (H has a slight positive in the amine and bonds to negative O in water)
- can be soluble in water but as gets longer, less soluble
features of alcohols
- hydroxyl functional group (OH)
how can an alcohol be formed?
a substation reaction where an alkane reacts with water or a strong base or OH-
primary alcohol
OH attacked to C and one other alkyl group
secondary alcohol
OH attacked to C and two others alkyl group
tertiary alcohol
OH attaches to C and three other alkyl groups
naming alcohols with priority
butan-1-ol
ol
naming alcohols without priority
2 hydroxy butanoic acid
properties of alcohols
- polar due to OH
- not symmetrical
- hydrogen bondning
- soluble in water (dependent on length)
what is an addition reaction?
when a small molecule is added and the double C-C bond is disrupted creating an entry point
how many products in addition reactions?
one
how is an alkane made from an alkene? what is this reaction called?
alkene plus H2 with UV/heat produces an alkane
- hydrogenation reaction
alkene to a halogenated alkane addition reaction
alkene plus HCl or Cl2 etc. with UV or heat forms a halogenated alkane
alkene to amine with addition reaction
alkene plus NH3 with UV/heat forms an amine
alkene to an alcohol addition reaction
alkene plus water with H3PO4 at 300 degrees forms an alcohol
how does an alcohol form a carboxylic acid?
primary alcohols are the reductant and undergo oxidation with an oxidant (Cr2O72-/H+ or MnO4-/H+). intense heat and long reaction time are needed
colour changes when redox reaction occurs
Cr2O72- is orange and Cr3+ is green
MnO4- is purple and Mn2+ is colourless
how is an aldehyde made?
intermediate step in forming carboxylic acids. primary alcohol reacts with Cr2O72-/H+ or MnO4-/H+ in mild conditions for less time
what is an aldehyde?
CHO group
- ends in al
how is a ketone made?
if a secondary alcohol is used to make carboxylic acids, ketones are formed
what are ketones?
C=O (carbonyl bond)
- ends in one
what does carboxylic acid being described as a weak acid mean?
does not fully ionise
neutralisation reaction where Ethnic acid reacts with sodium carbonate (Na2CO3)
CH3COONa, water and carbon dioxide form
neutralisation reaction where ethnic acid reacts with sodium hydrogen carbonate (NaHCO3)
CH3COONa, water and CO2 gas form
features of carboxylic acids
- polar due to asymmetry and hydrogen bonding
- soluble in water (dependent on length)
- highest priority
what are esters
synthetic flavours and fragrances
how is an ester formed?
reacting an alcohol with a carboxylic acid in a condensation reaction (esterification reaction)
- H2SO4 as catalyst
naming esters
- end with oate
- alcohol becomes an ‘yl’
formation of polyethene
addition polymerisation
ethene has bonds broken with UV and heat to form polyethene
how are polymers named?
in honour of the alkene
how is polyvinyl chloride formed?
vinyl chloride (CH2CHCl) has bonds broken with UV or heat and forms polyvinyl chloride
how is poly amide formed?
nothing on arrow
how is polystyrene formed?
styrene with UV and heat
- styrene has a benzene ring (C6H6) with one hydrogen lost
how is polypropene formed?
propene with UV and heat
polybutene
butene with UV and heat
how is a polyester formed?
nothing on arrow
what is covalent bonding?
the sharing of valence electrons between non-metal atoms so that each atom is able to acquire a full outershell
what are permanent dipoles?
2 non-metal atoms which have an electronegative discrepancy form a bond. The pull on the bonding electron pair is favoured by the atom with a greater electronegativity. This discrepancy creates poles (changes) along the bond.
what is hydrogen bonding?
a form of dipole-dipole bonding (inter) and dipole bond (intra)
-FONH
what is a dispersion force?
intermolecular bond
- weak
- instantaneous dipole
intermolecular bonds and their strength
strongest to weakest: H bond, dipole-dipole, dispersion
How is an amide formed?
carboxylic acid and an amine react
- water is condensed
- amide link (C=O NH) also called peptide link
- named ethyl ethanamide