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Organic Chemistry IB/SL_ALL
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Terms in this set (81)
nomenclature steps (5)
1.Find the longest carbon chain containing the principle functional group (highest-priority groups are generally the most oxidized)
2. Number the carbon chain so that the principle functional group gets LOWEST possible number
3. Proceed to number the chain so that the lowest set of numbers is obtained for the substituents (attachments)
4. Name the substituents (attachments) and determine the NUMBER of the carbon in which it is attached.
5. Complete the name by listing substituents (attachments) in alphabetical order; place commas between numbers and dashes between numbers and words
What is "R" mean?
Any CARBON attachment
alkane (ending..."ane")
All single bonded carbons.
alkene (ending..."ene")
Carbons bonded together with at least ONE double bond. Number carbons so that the double bond gets the LOWEST number.
C-C-C-C=C-C
This chain has 6 carbons. To number it you would need to number RIGHT to LEFT in order to give the double bond a #2 designation instead of a #5, if you were to number L-> R.
6= HEX
Double bond on the 2nd carbon
Name: 2-hexENE or hex-2-ene
alkyne (ending..."yne")
Carbons bonded together with at least ONE TRIPLE bond. Number carbons so that the double bond gets the LOWEST number.
C-C-C-C---C-C
*Cannot show bonds correctly. One on top of each other.
This chain has 6 carbons. To number it you would need to number RIGHT to LEFT in order to give the TRIPLE bond a #2 designation instead of a #5, if you were to number L-> R.
6= HEX
TRIPLE bond on the 2nd carbon
Name: 2-hexYNE or hex-2-yne
alcohol
Carbon attached to an R-OH
These have an -OH group (or more than one in the case of diols, triols etc) at any position in the chain.
halogenoalkane
Carbon attached to a halogen (any one of the halogens).
The halogen atom may be added into any position in the chain. If there is more than one then the prefixes di- tri- tetra- etc are used.
amine
Nitrogen attached to at least one carbon.
The NH2 group can go anywhere on the carbon chain. It infers basic characteristics to the molecule. (ability to accept a proton from an acid)
aldehyde
R-C-H (double bond on carbon)
||
O
Has a carbonyl C=O at the end of a carbon chain, with the carbon also attached to a hydrogen
ketone
R-C-R' (double bond on carbon)
||
O
Has a carbonyl group C=O but it is in the middle of a carbon chain and the carbon has no hydrogens attached
carboxylic acid
R-C-OH (double bond on carbon)
||
O
The group must go at the end of a carbon chain as it has a carbon attached to an oxygen by a double bond and also an -OH group (leaving the carbon with only one other bond which it uses to attach to the rest of the carbon chain)
ester
R-C-O-R (double bond on carbon)
||
O
Linked compound formed by condensation reactions between carboxylic acids (or compounds deriving from them) and alcohols. They also occur naturally and may be polymers (polyester) see amide linkage above
amide
R-C-N (double bond on carbon)
||
O
Regarded as derivatives of carboxylic acids in which the hydroxyl group has been replaced by an amine or ammonia.
aldehyde suffix
-al
ketone suffix
-one
ester suffix
-ate
amide suffix
-amide
aldehyde suffix
-al
carboxylic acid suffix
-ic
alcohol suffix
-ol
ether ending
-ether
Homologous series compounds will differ by
CH2
As chain gets longer, boiling point
increases (due to increased intermolecular forces)
Define isomers
Different compounds with the same molecular formula
Alkanes (C-C):
a) Reactivity? Why?
b) Can they combust? Always fullY?
c) Saturated or unsaturated?
a) unreactive due to lack of strength and polarity of bonds
b) Full produces: CO2 + H2O (Very exothermic)
Not full produces: CO + H2O
c) Saturated: completely filled with hydrogens if not connected to another carbon (all single bonds)
Alkanes undergo what type of reactions?
*Conditions needed
*Free radical substitution reactions
Need: Pure halogen, UV light, room temperature
Alkenes undergo ___ reactions. Explain
Addition reactions. Alkenes get attacked by electrophiles and get saturated. The bonds become single, and so electrophile joins on to both carbon atoms.
Hydrogenation, Halogenation, Hydration Conditions
High pressure, temperature, nickel catalyst
No heat, catalyst or UV light required
High temperature, pressure, heated catalyst. Reaction is reversible. Alternative to fermentation
To distinguish between alkanes and alkenes use
Bromine water.
Alkane will stay orange and decolourise in UV light
Alkene will decolourise quickly
Solubility of alcohols
As the size of chain increases, solubility decreases because more energy is required to overcome hydrogen bond. Smaller relative to rest of molecule
Oxidizing agent for alcohols
Acidified Potassium Dichromate (Cr2O7 2- / H+) or Acidified Potassium Permangenate (MnO4 2- / H+)
Primary alcohols oxidize to ___.
They can be collected by
Aldehyde to Carboxylic Acid
Aldehydes have much lower boiling points than alcohols and carboxylic acids, as there is no hydrogen bonding, so intermolecular forces are weaker. This can be collected by boiling off and distilling immediately. To collect carboxylic acid, use a condenser in a vertical position and collect under reflux. The aldehyde vapor is returned back to reaction chamber and further oxidized to carboxylic acid
Reaction equation for primary alcohols (eg. ethanol)
CH₃CH₂OH + [O] --> (above arrow with catalyst) CH₃COOH
Secondary alcohols oxidize to
They can be collected by
Ketone
Heating under reflux
Reaction equation for secondary alcohols
CH₃CH(OH)CH₃ + [O] --> (catalyst above arrow) CH₃COCH₃
Oxidation of tertiary alcohols
Cannot be further oxidised as there are no more hydrogens that can be replaced.
ALKENE → DIHALOGOENALKANE Reaction
*List what must be present for reaction to occur (catalysts)
*List what type of reaction
Halogent
RXN: Addition or halogenation
ALKENE → ALKANE reaction
*List what must be present for reaction to occur (catalysts)
*List what type of reaction
H₂, CATALYST: Ni /150°C
RXN: Addition or Hydrogenation
ALKENE → HALOGENOALKANE
*List what must be present for reaction to occur (catalysts)
*List what type of reaction
HCl (usually see HCl...but can be HBr...HI...etc.)
RXN: Halogenation
ALKENE → ALCOHOL
*List what must be present for reaction to occur (catalysts)
*List what type of reaction
H₂O CATALYST: H₂SO4/ 170°C
RXN: Hydration
ALKENE → CO₂ & WATER
*List what must be present for reaction to occur (catalysts)
*List what type of reaction
O₂
RXN: Combustion
ALKENE → ADDITION POLYMERS
*List what must be present for reaction to occur (catalysts)
*List what type of reaction
TiCl₃ or Zeigler-Natta catalyst
RXN: Addition polymerization
Alkane to CO₂ & water
*List what must be present for reaction to occur (catalysts)
*List what type of reaction
O₂
Combustion
Halogenoalkane to alcohol
*List what must be present for reaction to occur (catalysts)
*List what type of reaction
warm OH⁻
Nucleophilic substitution
Halogenoalkane to Di/tri/tetrahalogenoalkane
*List what must be present for reaction to occur (catalysts)
*List what type of reaction
Warm OH-
Nucleophilic substitution
Alcohol to Ketone
*List what must be present for reaction to occur (catalysts)
*List what type of reaction
2° alcohol, Cr₂O₇²⁻, H₂SO₄, heat
Oxidation
Alcohol to CO+H₂O
*List what must be present for reaction to occur (catalysts)
*List what type of reaction
O₂
Partial Combustion
Alcohol to aldehyde
*List what must be present for reaction to occur (catalysts)
*List what type of reaction
2° alcohol, Cr₂O₇²⁻, H₂SO₄, heat
Oxidation/DISTILLATION (orange ion color)
Aldehyde to Carboxylic acid
*List what must be present for reaction to occur (catalysts)
*List what type of reaction
2° alcohol, Cr₂O₇²⁻, H₂SO₄, heat
Oxidation/REFLUX (green ion color)
Alcohol to Carboxylic acid
*List what must be present for reaction to occur (catalysts)
*List what type of reaction
2° alcohol, Cr₂O₇²⁻, H₂SO₄, heat
Oxidation/REFLUX (green ion color)
Alkene to CO & water
*List what must be present for reaction to occur (catalysts)
*List what type of reaction
O₂
Partial combustion
Show the formula, condensed structural formula, and structural formula for methane.
Formula:: CH4
Condensed: CH4
Structural:
Show the formula, condensed structural formula, and structural formula for butane.
Formula: C3H6
Condensed: CH3CH2CH2Ch3
Structural
what is the difference between aldehydes and ketones
aldehydes: hydrogen is attached to the carbon and the double bond of oxygen
Ketones: no hydrogen
What happens to the the physical properties of homologous series as the carbon chain increases?
boiling point increases
What is fractional disillation
physical separation process that uses differences in boiling points to separate the mixture
What is benzene?
aromatic, unsaturated hydrocarbon
what are hydrocarbons
Compounds containing only carbon and hydrogen
empirical formula
the simplest whole number ratio of the atoms the molecule contains
molecular formula
the actual number of atoms of each element present in the molecule
skeletal formula
most basic form: each corner means a carbon and each carbon has hydrogen atoms connected that are not shown
Propane:
structural formula
a representation of the molecule showing how the atoms are bonded to each other
-ane
alkane
-ene
alkene
-yne
alkyne
-anol
alcohol
-anamine
amine
-anal
aldehyde
-anone
ketone
-anoic acid
carboxylic acid
-anoate
ester
secondary carbon atom
carbon atom in an organic molecule that is attached to the functional group, one hydrogen atom and two alkyl groups
tertiary carbon atom
carbon atom in an organic molecule that is attached to the functional group and three alkyl groups
alkane + halogen
halogenoalkane + hydrogen halide
alkene + hydrogen
alkane
alkene + hydrogen context
nickel catalyst; 150 deg
alkene + halogen
dihalogenoalkane
alkene + hydrogen halide
halogenalkane
alkene + water
alcohol
alkene + water context
concentrated sulphuric acid catalyst; heat with steam
test to distinguish between primary or secondary alcohol, and tertiary alcohol
potassium dichromate colour change from yellow /orange to greenish
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