Organic chemistry Flashcards
Carbon electron arrangement:
2,4
Because Carbon has four valence electrons….
carbon atom will covalently bond to 4 other carbon atoms.
Define the term hydrocarbon.
The simplest organic compounds that contain only hydrogen atoms and carbon atoms.
Structural formula:
shows how atoms are joined together
Condensed structural formula:
is used to represent organic compounds especially for larger molecules.
Molecular formula:
gives information about the type and number of atoms present in a substance.
Define the term homologous series
Is a family of organic compounds that can be represented by a general formula in which each successive member of the series differs by a -CH2- unit. Often have similar chemical properties.
Define the term functional group
Atoms or groups of atoms which influence the chemical behaviour of a compound.
Define the term ‘ saturated hydrocarbon’
Hydrocarbons that contain only single bonds between carbon atoms.
Alkane general formula:
CnH2n+2
Constitutional/structural isomers
have the same molecular formula but their atoms are connected differently.
Describe and explain the common physical properties of alkanes such as physical state, solubility, and trends in melting point and boiling point.
(1. Colour
2. solubility
3. Conductivity
4. melting/boiling points)
- Colourless compounds
Are non-polar and hence are insoluble in water - Have densities less than water so they float on water
- Do not conduct head or electricity because they do not contain ions or electrons which are free to move.
- Show increased melting and boiling points as the length of the carbon chain increases.
Know the substitution reactions of alkanes with halogens
- Loss of hydrogen atom - involves breaking a C-H bond
- Replacement of the lost hydrogen with a halogen atom
- The presence of a catalyst - usually UV light.
Alkene general formula:
CnH2n
Define the term geometrical isomers
when the atoms in the molecule have the same order of connectivity but different arrangement in space.
Cis isomers
the same groups are on the same side of the double bond.
Trans isomers
the same groups are on opposite sides of the double bond
Explain the reasons for existence of cis-trans isomers in alkenes
Geometric isomerism exists because free rotation around the carbon-carbon double bond cannot occur, fixing the position in space of the groups attached to the carbon atoms of the double bond.
Describe and explain the common physical properties of alkenes such as physical state, solubility, conductivity and trends in melting point and boiling point.
- Solubility
- melting point
- Density
- State
- insoluble in water
- Show increase in melting point as chain length (molar mass) increases
- Less dense than water
- At room temperature, ethene, propene, and butene are gases. Alkenes of higher molar mass are liquids.
addition reactions of alkenes with Halogenation (Cl2, Br2) reaction
is an addition reaction where a halogen molecule (two halogen atoms), usually chlorine or bromine, add across the double bond.
Know the addition reactions of alkenes with (H2)
is an addition reaction where a hydrogen atom (two hydrogen atoms) add across the double bond of an alkene to form an alkane molecule. A catalyst, usually nickel at 150°C or platinum at room temperature
Know the addition reactions of alkenes with Hydration (H2O)
Hydration is an addition reaction in which an alkene reacts with steam, water, to from an alcohol. In this reaction double bond is broken. One carbon of the double bond accepts a hydrogen, and the other accepts OH.
Know and explain Markovnikov’s rule for addition reactions.
In asymmetrical alkenes, the carbon of the double bond that has more hydrogen atoms receives the hydrogen forming the major product.
Major product -
formed in large quantities
Minor product -
formed in small quantities
Define the term unsaturated.
a molecule that contains double or triple carbon bonds.
Test for alkene/ alkane using Br2
Bromine is used to test for unsaturation, since bromine loses its brown colour when it reacts with alkenes. Alkenes react readily react without catalyst, whereas alkanes require sunlight and react slowly.
Test for alkene/ alkane using MnO4⁻
When the reaction is carried out in acidic conditions, purple-coloured permanganate decolourises to form Mn2+ ions when in prescence of alkene. In the acidic conditions, further oxidation of the diol occurs.
Substitution
An atom is replaced by another atom/group of atoms.
Addition
One bond of the carbon double bond breaks and an atom/ group of atoms adds to each of the adjacent carbon atoms. The organic product is saturated.
Polymer
large molecules made of many small repeating units known as monomers.
Monomer
atoms or small molecules that bond together to form more complex structures such as polymers.
Explain how addition polymers are formed from alkenes
Alkenes form addition polymers in a polymerisation reaction. Carbon-carbon double bond is broken, to form polymers.
Alkyne general formula:
CnH2n-2
What is the solubility of alkynes
Alkynes are insoluble in water.
What is the density of alkynes
Less dense than water
What is the boiling point of alkynes
Boiling point of alkynes increase with higher molar mass as the intermolecular forces increase. Hence more energy is needed to overcome these forces of attraction.
Primary haloalkane
The carbon atom to which the halogen is attached is further attached to one carbon atom.
Secondary haloalkane
The carbon atom to which the halogen is attached to is further attached to two other carbon atoms.
Tertiary haloalkane
The carbon atom to which the halogen is attached is further attached to three other carbon atoms.
Describe and explain the common physical properties of haloalkanes such as physical state, solubility and trends in melting point and boiling point.
- Colour/odour
- Solubility
- Boiling point in relation to alkanes
- Boiling point in relation to size
- Colourless odourless compounds.
- Hydrophobic in nature.
- Haloalkanes have higher boiling point than alkanes, if the number of carbon atoms is the same.
- The boiling point of haloalkanes increases with the increasing number of halogens in haloalkanes.
Know the reaction of haloalkanes with ammonia.
Haloalkanes undergo substitution reaction with ammonia. The halogen is removed and replaced by NH2 to form amines.
Know the reaction of haloalkanes with aqueous potassium hydroxide or sodium hydroxide.
Haloalkane undergoes substitution reaction where halogen is replaced by OH, to produce an alcohol.
Know and explain the elimination reaction of haloalkanes with alcoholic potassium hydroxide or sodium hydroxide
Haloalkane undergo elimination with alcoholic potassium hydroxide or sodium hydroxide which involves the removal of the halogen atom and an adjacent carbon atom. Forming a double bond - alkene.
Major product is formed when the Carbon with the least number…
of hydrogen atoms has a hydrogen atom removed.
Minor product is formed when Carbon atom with the most….
number of hydrogen atoms has a hydrogen atom removed.
Know and explain Saytzeff’s rule for elimination reactions
The carbon atom with fewer hydrogen atoms loses a hydrogen atom to form the major product. “Poor gets poorer”
Primary alcohols
the carbon atom carrying the OH group is bonded to one other carbon atom or no other carbon atom.
Secondary alcohols
Carbon atom carrying the OH group is bonded to 2 other carbon atoms
Tertiary alcohols
Carbon atom carrying the OH group is bonded to 3 other carbon atoms.
Solubility of alcohols (over view)
Small carbon atoms are very soluble in water. The presence of - OH group makes these molecules polar and allows hydrogen bonding with water molecules.
Solubility of alcohols…specific alcohols
- Methanol, ethanol, propanol - very soluble
- Butanol - soluble
- Pentanol, hexanol - slightly soluble
- Alcohols more than 6 carbon atoms is insoluble
Alcohol melting point
are much higher than those of corresponding alkanes, because hydrogen bonds can form between alcohol molecules. These hydrogen bonds are stronger than the intermolecular forces between alkane molecules.
Alcohol boiling point
boiling point of alcohols increase with the increasing size of the molecules. This is because as the number of electrons in a molecule increases, the intermolecular forces become stronger.
Know the oxidation reactions of alcohols with oxidising agents (MnO4-/H+, Cr2O7-/H+). Using Ethanol
CH3CH2OH → (MnO4-/H+, Cr2O7-/H+) CH3COOH
Know and explain the elimination reaction that occurs when alcohols react with conc. H2SO4.
Removing a water molecule from an alcohol produces an alkene molecule. The -OH group and a hydrogen atom from a carbon atom adjacent to the carbon atom bonded to -OH is removed.
CH3CH2OH → (conc.H2SO4.) CH2 = CH2 + H2O
Know and explain Saytzeff’s rule for elimination reactions.
The carbon atom with fewer hydrogen atoms loses a hydrogen atom to form the major product. “Poor gets poorer”
Know the substitution reaction of alcohol with hydrogen halides, PCI3, PCI5, SOCl2. generalisation.
The -OH group of an alcohol molecule can be replaced by a halogen atom to form a haloalkane molecule.
What is the carboxylic acid with one carbon atom
methanoic acid
What is the carboxylic acid with two carbon atoms
ethanoic acid
What is the carboxylic acid with three carbon atoms
propanoic acid
What is the state of carboxylic acids
colourless liquids or white solids at room temperature
What is the smell of carboxylic acids
low molar mass carboxylic acids have unpleasant odours.
What is the melting point of carboxylic acids
carboxylic acids have higher melting and boiling points than alkanes, alkenes, alkynes, and alcohols, as carboxylic acids can form hydrogen bonds with each other.
What is the solubility of carboxylic acids in water.
carboxylic acids with low molar mass like methanoic and ethanoic acid are soluble in water as it can form hydrogen bonds with the water molecules. Solubility decreases as non-polar carbon chain increases.
Identify carboxylic acids using their acidic properties
- Litmus paper
- Electricity conductivity
- reaction with metal
- React with bases
- React with carbonates and hydrogenate carbonates
- Turn blue litmus paper red
- Conduct electricity - because sufficient number of ions are present and free to move
- React slowly with metals such as magnesium to form hydrogen gas
- React with bases such as sodium hydroxide solution in a neutralisation reaction, forming water.
- React with carbonates and hydrogenate carbonates to form water and carbon dioxide gas.
Amines general formula:
CnH2n+1NH2
Identify amines:
Amines are weak bases. They change moist red litmus paper blue.
Boiling points of amines
Amines have a higher boiling point than alkanes. This is due to the fact that amines can form hydrogen bonds with other amine molecules. More energy is needed to overcome the strong hydrogen bonds hence higher boiling points.
Solubility of amines
Low molecular amines are soluble in water as it can form hydrogen bonds with water molecule.
Amines are weak bases as they…
accept a proton from water. Bases (in this case -organic) are proton acceptors.
CH3CH2NH2 + HCl →
CH3CH2NH2ᐩCl⁻
CH3CH2NH2 + CH3COOH →
CH3CH2NH3ᐩCH3COO⁻
Alkane to Haloalkane
Reagent: ?
Condition: ?
Type of reaction:
Reagent: Br2 or Cl2
Condition: UV light and/or heat to occur
Type of reaction: substitution
Complete the alkane to haloalkane reaction:
CH3CH3 + Br2 →
CH3CH2Br + HBr
Haloalkane to alcohol
Reagent: ?
Condition: ?
Type of reaction: ?
Reagent: KOH (aq)
Condition: Aqueous (water)
Type of reaction: Substitution
Complete the haloalkane to alcohol reaction
CH3CH2Br + KOH(aq) →
CH3CH2OH
Haloalkane to Amine
Reagent: ??
Condition: ??
Reaction type: ??
Haloalkane to Amine
Reagent: Conc. NH3 (alc.)
Condition: Concentrated and alcoholic.
Reaction type: substitution
Complete the haloalkane to amine reaction
CH3CH2Br + Conc. NH3(alc)→
CH3CH2NH2
Alkene to Alkane
Reagent: ??
Condition: ??
Reaction type: ??
Alkene to Alkane
Reagent: H2
Condition: Ni catalyst
Reaction type: Addition
Complete the alkene to alkane reaction:
CH2=CH2 + H2/Ni →
CH3CH3
Alkene to Haloalkane
Reagent: ??
Reaction type: ??
Alkene to Haloalkane
Reagent: Br2 or Cl2
Reaction type: addition
Complete the alkene to alkane reaction:
CH2=CH2 + Br2 →
CH2BrCH2Br
Alkene to Alcohol
Reagent: ??
Condition: ??
Reaction type: ??
Alkene to Alcohol
Reagent: H2O/ Hᐩ heat
Condition: acid and heat
Reaction type: addition
Complete the Alkene to Alcohol reaction:
CH2=CH2 + H2O/H+, heat →
CH3CH2OH
Alcohol to Alkene
Reagent: Conc. ??
Reaction type: ??
Alcohol to Alkene
Reagent: Conc. H2SO3
Reaction type: elimination
Complete the Alcohol to alkene reaction
CH3CH2OH + Conc. H2SO4→
CH2=CH2
Haloalkane to Alkene
Reagent: ??
Condition: ??
Type of reaction: ??
Haloalkane to Alkene
Reagent: KOH(alc), heat
Condition: alcoholic and heat
Type of reaction: elimination
Complete the haloalkane to alkene reaction
CH3CH2Cl + KOH(alc), heat→
CH2=CH2
Alkene to Diol
Reagent: ??
Reaction type: ??
Alkene to Diol
Reagent: MnO4⁻ …. The MnO4⁻ has purple colour MnO4⁻ is reduced to brown MnO2(s)
Reaction type: Oxidation
Complete the alkene to diol reaction:
CH2=CH2 + MnO4-→
CH2OHCH2OH
(Primary) Alcohol to Carboxylic Acid
Reagent: ?? (two)
Condition: ??
Reaction type: ??
(Primary) Alcohol to Carboxylic Acid
Reagent: With MnO4-/H+, heat (colour change - purple MnO4-(aq) to colourless Mn2+(aq))
OR
With Cr2O72-/H+, heat (colour change - orange Cr2O72-(aq) to green Cr3+(aq))
Condition: heat/warm
Reaction type: Oxidation
Complete the Alcohol to Carboxylic Acid reaction:
C2H5OH + MnO4- / H+→
CH3COOH
Carboxylic acids with water
Reagent: ??
Reaction type: ??
Carboxylic acids with water
Reagent: H2O
Reaction type: oxidation
Complete the carboxylic acids with water reaction
CH3COOH + H2O ⇌
CH3COO- + H3O+
Carboxylic acids with reactive metal
Reagent: ??
Reaction type: ??
Carboxylic acids with reactive metal
Reagent: Mg (a reactive metal)
Reaction type: oxidation
Complete the carboxylic acids with reactive metal:
2CH3COOH + Mg→
(CH3COO)2Mg + H2
Carboxylic acids with NaOH
Reagent: ??
Reaction type : ??
Carboxylic acids with NaOH
Reagent: NaOH
Reaction type : neutralisation
Complete the carboxylic acid with NaOH reaction:
CH3COOH + NaOH →
CH3COONa + H2O
Carboxylic acids with NaHCO3, CaCO3
Reagent: ??
Reaction type: ??
Carboxylic acids with NaHCO3, CaCO3
Reagent: NaHCO3 , CaCO3
Reaction type: neutralisation
Complete the Carboxylic acids with NaHCO3, CaCO3 reaction:
CH3COOH + NaHCO3→
CH3COONa + H2O + CO2
Amines with water
Reagent: ??
Reaction type: ??
Amines with water
Reagent: H2O
Reaction type: neutralisation
Complete the Amines with water:
CH3CH2NH2 + H2O ⇌
CH3CH2NH3+ + OH-
Amines and HCl
Reagent: ??
Reaction type: ??
Amines and HCl
Reagent: HCl(aq)
Reaction type: neutralisation
Complete the Amines and HCl
CH3CH2NH2 + HCl→
CH2CH2NH3+Cl-