Organic Chemistry IB/SL_ALL

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

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.

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.

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)

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

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)

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

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

aldehyde suffix

carboxylic acid suffix

Homologous series compounds will differ by

As chain gets longer, boiling point

increases (due to increased intermolecular forces)

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

carboxylic acid

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

alkene + hydrogen context

nickel catalyst; 150 deg

alkene + halogen

dihalogenoalkane

alkene + hydrogen halide

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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