Module Seven - Organic Chemistry Flashcards
Nomenclature Hydrocarbons Products of Reactions Involving Hydrocarbons Alcohols Reactions of Organic Acids and Bases Polymers
how many types of carbon bonds are there?
3 (single, double, triple)
what are the first eight prefixes in naming alkanes/alkenes/alkynes?
1: meth-
2: eth-
3: prop-
4: but-
5: pent-
6: hex-
7: hept-
8: oct-
what determines that a compound is an alkane?
only has single bonds
what determines that a compound is an alkene?
has at least one double bond
what determines that a compound is an alkyne?
has at least one triple bond
what is the general formula for alkane?
CnH(2n+2)
can alkanes be both straight-chained and branched?
yes
what are the two types of alkanes (structure-wise)?
- straight-chained
- branched
what is the prefix of a based on when naming a compound?
the longest chain in the compound (parent chain)
how are substituents ordered when naming a compound?
in alphabetical order
what is the purpose of the numbers before the substituents when naming a compound?
shows the position of the substituent on the parent chain
which end do you start counting from when naming a compound?
- the end with the more significant section of the compound (functional group)
- smallest addition of substituent positions
what is the general formula for alkene?
CnH2n
what is the general formula for alkyne?
CnH(2n-2)
how is the position of a bond named in an alkyne/alkene?
by putting the number position in front of the name
e.g. 2-butyne
what are halogenated organic compounds?
compounds where a hydrogen/s is replaced with a halogen (haloalkanes)
how are halogens included when naming halogenated organic compounds?
- similar to substituents
- -ine is replaced with -o
- if appeared multiple times, write all positions
- alphabetical order
what are a few halogens?
fluorine, bromine, iodine, chlorine
what are isomers?
same molecular formula but different structure
what are the three types of structural isomers?
chain, functional group, position
what are a few uses of alkanes?
- methane: main component of natural gas
- propane: liquid petroleum gas
can hydrocarbons conduct electricity?
no
why can’t hydrocarbons conduct electricity?
lack of dipole or ionic charges
are hydrocarbons soluble in water?
no
why aren’t hydrocarbons soluble in water?
they are non-polar
can hydrocarbons dissolve in non-polar substances?
yes!!!
why can hydrocarbons only be dissolved in non-polar substances?
like dissolves like babey
do hydrocarbons have low melting and boiling point?
yes
why are hydrocarbons have low melting and boiling point?
formation of weak dispersion forces between molecules
what are chain isomers?
- same molecular formula
- the length in parent chain is different
what are functional group isomers?
- same molecular formula
- different functional groups
what are position isomers?
- same molecular formula
- probably same parent chain length
- positions of substituents are different
what are functional groups?
particular groups of atoms that allow for ‘families’ of organic compounds to share similar chemical properties
what are homologous series?
series or ‘families’ of compounds with different functional groups
what functional group belongs to alcohol?
hydroxyl group (-OH)
what functional group shows aldehyde?
double bonded O in last carbon
what functional group shows a ketone?
double bonded O on a middle carbon
what functional group shows a carboxylic acid?
double bonded O and hydroxyl (-OH) on last carbon
what functional group shows an ester?
double bonded O, single-bonded O, with an R chain
what functional group shows an amine?
-NH2
what functional group shows an amide?
double bonded O with NH2 on last carbon
what is the suffix for a haloalkane?
-ane
what is the suffix for alcohols?
-ol
what is the suffix for aldehydes?
-al
what is the suffix for ketones?
-one
what is the suffix for carboxylic acids?
-oic acid
what is the suffix for esters?
alkyl -oate
what is the suffix for amines?
-amine
what is the suffix for amides?
-amide
what is an example of a haloalkane?
bromoethane
what is an example of an alcohol?
ethanol
what is an example of an aldehyde?
propanal
what is an example of a ketone?
propanone
what is an example of a carboxylic acid?
ethanoic acid
what is an example of an ester?
methyl ethanoate
what is an example of an amine?
ethanamine
what is an example of an amide?
methanamide
what are a few uses of alcohol?
- beverages
- additive to petrol
- solvent in medicine
what is the general formula for alcohol?
CnH(2n+1)OH
what are the three types of alcohols?
- primary (1°)
- secondary (2°)
- tertiary (3°)
what is a primary alcohol?
one carbon atom is bonded to the carbon atom with the -OH
what is a secondary alcohol?
two carbon atoms are connected to the carbon atom with -OH
what is a tertiary alcohol?
three carbon atoms are connected to the carbon atom with -OH
what are the two factors that affect the properties of alcohols (boiling point and solubility)?
- presence of the -OH group
- size of the hydrocarbon chain
do alcohols have a higher boiling point than alkanes/alkenes/alkynes?
yes
why do alcohols have a higher boiling point than alkanes/alkenes/alkynes?
- presence of -OH
- -OH can make hydrogen bonds between other -OH of the alcohol molecules
- strength of hydrogen bonds is much greater than weak dispersion forces
is solubility of alcohols affected by the ratio between the polar -OH and non-polar hydrocarbon section?
yes
how is solubility of alcohols affected by the ratio between the polar -OH and non-polar hydrocarbon section?
- small alcohols: effect of polar -OH group outweighs the non-polar hydrocarbon (very soluble)
- larger alcohols: effect of the non-polar section outweighs the polar functional group (insoluble)
why are some larger alcohol soluble in water?
may have multiple hydroxyl groups that multiply the polarity
what is an example of a large soluble alcohol molecule?
glucose (5 hydroxyl groups!!!)
is the hydroxyl group polar?
yes
does chain length affect solubility in alcohols?
yes
what are the two main types of carbonyl compounds?
aldehydes + ketones
what is the difference between a ketone and aldehyde?
the double bond in aldehydes are at the end of the chain, while ketones are in the middle
what is an example of a functional group isomer?
aldehyde and ketones
what are dipole-dipole bonds?
attractive forces between the positive end of one polar molecule and the negative end of another polar molecule
do aldehydes and ketones have higher boiling points than hydrocarbons?
yes
why do aldehydes and ketones have higher boiling points than hydrocarbons?
dipole-dipole bonds
do aldehydes and ketones have higher boiling points than alcohols?
no
why do aldehydes and ketones have lower boiling points than alcohols?
hydrogen bonds are stronger than dipole-dipole bonds
are aldehydes and ketones more soluble than hydrocarbons?
yes
why are aldehydes and ketones more soluble than hydrocarbons?
the carbonyl group is highly polar
are aldehydes and ketones more soluble than alcohols?
no
why are aldehydes and ketones less soluble than alcohols?
hydroxyl group is more polar than carbonyl group
does chain length affect solubility of aldehydes and ketones?
yes
how does chain length affect aldehyde and ketone solubility in water?
as chain length increases, solubility decreases (non-polar outweighs polar)
what is the general formula of aldehydes?
RCHO
what is the general formula of ketones?
RCOR’
what is the general formula for carboxylic acids?
CnH(2n+1)COOH
what is the common name for acetic acid?
vinegar
what functional group contains are carboxyl group?
carboxylic acid
what is a carboxyl group?
contains a carbonyl (C=O) and hydroxyl (-OH) together
what is another name for ethanoic acid?
acetic acid (CH3COOH)
do carboxylic acids have a higher boiling point than hydrocarbons?
yes
do carboxylic acids have a higher boiling point than alcohols?
yes
do carboxylic acids have a higher boiling point than aldehydes and ketones?
yes
why do carboxylic acids have a higher boiling point than hydrocarbons, alcohols and aldehydes/ketones?
as two carboxylic acid molecules can form TWO hydrogen bonds with one another
does chain length affect the solubility of carboxylic acids?
yes (larger = less soluble)
are carboxylic acids weak or strong?
weak
what type of acids are carboxylic acids?
weak monoprotic acids
what is a monoprotic acid?
acid donates only one proton or hydrogen atom per molecule to an aqueous solution
are carboxylic acids soluble in water?
small carb acids are soluble
how are carboxylic acids soluble in water?
the carboxyl group forms h-bonds with the water
what does it mean when an acid is weak?
will only partially ionise in water
how is an amide formed from an amine?
amine + carboxylic acid –> amide
what is the general formula for amines?
RNH2
what are the three types of amines?
primary, secondary, teritary
what is a primary amine?
has one alkyl group attached to the nitrogen
what is a secondary amine?
has two alkyl groups attached to the nitrogen
what is a tertiary amine?
has three alkyl groups attached to the nitrogen
are amines polar?
yes
how are amines polar?
nitrogen is very electronegative (NH2 is very polar)
why can’t tertiary amines form hydrogen bonds?
there are no hydrogens connected to the nitrogen in a teritary amine
do amines have a higher a boiling point than alcohols?
no
why do amines have a lower a boiling point than alcohols?
nitrogen is less electronegative than oxygen
are amines soluble in water?
yes (small primary and secondary)
why are amines soluble in water?
hydrogen bonding
are tertiary amines soluble?
no
why are tertiary amines insoluble?
lack a N-H bond to create h-bonds with the water
why is the boiling points of tertiary amines lower than primary and secondary amines?
lacks a N-H bond, so therefore cannot form hydrogen bonds
from what functional group are amides derived from?
carboxylic acids
how are amides derived from carboxylic acids?
when the -OH of the carb acid is replaced by -NH2 (amine)
what structural unit do all amides have?
-CO-NH-
how many types of amides are there?
three
what are the three types of amides?
primary, secondary, tertiary
what is a primary amide?
only one alkyl group attached to the -CO-NH-
what is a secondary amide?
has two alkyl groups attached to the -CO-NH-
what is a tertiary amide?
has three alkyl groups attached to the -CO-NH-
what is the genral formula of amides?
RCONHR’
is the boiling point of a tertiary amide lower than primary and seconday amide?
yes
why is the boiling point of a tertiary amide lower than primary and seconday amide?
has no N-H bond to form hydrogen bonding
why do amides generally have a high melting-boiling point and solubility?
has two polar bonds to create strong intermolecular bonds
what are the three ways an organic compound can enter the body?
inhalation, absorption, and ingestion
what is the effect of inhaling an organic compound?
organic compound will dissolve in the blood through the lungs and travel throughout the body, where it can accumulate
what is the effect of absorbing an organic compound through the skin?
the compound will dissolve through the skin and enter the bloodstream and travel throughout the body, accumulating inside organs
what is the effect of ingesting an organic compound?
the organic compound will be dissolved in the stomach, entering the bloodstream, and travel around the body, accumulating in organs
what are the hazardous physical properties of organic compounds?
volatility, flash point
what does volatile mean?
easily evaporated in regular temperatures
are most organic compounds volatile?
yes
why are compounds being volatile dangerous?
colourless vapours can fill the room and be inhaled
what makes an organic compound volatile?
weak intermolecular forces
what does flashpoint mean?
degree of flammability (lowest temperature a compound can be at before being ignited)
what are a few symptoms of skin contact with dangerous organic compounds?
burning or tingling, rashes, welts, chemical burns
what are the two levels of organic chemical poisoning?
acute, chronic
what are the symptoms of acute organic compound poisoning?
headaches, dizziness, affected reaction time and vision, poor coordination
what are the symptoms of chronic organic compound poisoning?
fatigue, physical weakness, mood swings, liver/kidney damage
how does one end up suffering from chronic organic compound poisoning?
after repeated exposure of years
what are the methods of prevention in the safety of using organic compounds?
minimisation, isolation, ventilation
how does minimisation help prevent organic compound poisoning?
by reducing (minimising) the use of particular dangerous compounds
how does isolation help prevent organic compound poisoning?
physical separation from chemicals can reduce exposure significantly
what are a few examples of small-scale isolation when handling organic compounds?
lab coat, goggles, gloves
how does ventilation help prevent organic compound poisoning?
draws fumes away from the user
what are the two levels of ventilation when handling organic compounds?
small-scale, large-scale
what does small-scale ventilation include when handling organic compounds?
fume cupboard that will draw fumes upwards and away from the user
what does large-scale ventilation include when handling organic compounds?
giant extractor systems that clear room and factory vapours
who deals with organic waste?
chemical waste disposal companies
what is the main disposal rule when handling organic compounds?
to not wash down the sink
why is it inappropriate to wash organic compounds down the sink?
chemicals will accumulate in sewer systems, and thus into our water ways, which’ll poison aquatic life
what are the methods used by larger companies when dealing with organic waste?
- neutralisation: removal of acid and base
- filtration: removal of solid particles
are double and triple carbon bonds weaker than single carbon bonds?
no, they are stronger
are alkenes and alkynes more reactive than alkanes?
yes
can alkenes and alkynes undergo combustion?
yes
what is combustion?
substances are burnt in the presence of oxygen, releasing energy
what are the two types of combustion?
complete and incomplete
what makes the difference between complete and incomplete combustion?
- the amount of oxygen present
- production of carbon/carbon monoxide
what is an addition reaction
the addition of atoms by breaking the double or triple bond
what substances can be reacted with an alkene/alkyne in an addition reaction?
- hydrogen (H2)
- water (H2O)
- hydrogen halides (HX)
- halogens (X2)
what hydrocarbons can undergo addition reactions?
alkenes and alkynes
what is the addition of hydrogen in an addition reaction?
hydrogenation
what is hydrogenation?
the addition of hydrogen to an alkene/alkyne in an addition reaction
what are alkenes converted to in an addition reaction?
alkanes
what is required in the process of hydrogenation?
metal catalyst
are alkenes unsaturated or saturated?
unsaturated
are alkynes unsaturated or saturated?
unsaturated
what are alkynes converted to in an addition reaction?
alkenes
what is the addition of halogens called in an addition reaction?
halogenation
what is halogenation?
the addition of halogens to an alkene/alkyne in an addition reaction
what is a hydrogen halide?
molecule with a hydrogen atom and halogen atom
what are a few examples of hydrogen halides?
hydrogen chloride, hydrogen bromide
what is the addition of water called in an addition reaction?
hydration
what is hydration in an addition reaction?
the addition of water to an alkene/alkyne in an addition reaction
what substance is required for water to be added to an alkene/alkyne in an addition reaction?
dilute sulfuric acid catalyst
what is a popular chemical that is produced through hydration (addition reaction)?
ethanol
what will be produced through the hydration of an alkyne?
ketone
what are the two reactions involving saturated hydrocarbons?
combustion, substitution with halogens
can all hydrocarbons undergo combustion?
yes!
what is required for alkanes to undergo halogen substituion?
UV light
what is produced when alkanes under halogen substitution?
haloalkanes
what does halogen substitution in alkanes include?
a halogen atom substitutes for a hydrogen atom
what two elements is optimal for halogen substitution in alkanes?
chlorine and bromine
why is UV light required in halogen substitution in alkanes?
will not occur unless sufficient amounts of energy is supplied
what is a qualitative experiment that models halogen substitution?
bromine water experiment