(CHEM) Topic 10 - Organic Chemistry

4 characteristics of a homologous serier

• Same functional group

• Same general formula, differing by CH₂

• Similar chemical properties

• Gradually changing physical properties (as chain gets longer)

ALKANE - general formula

C_nH_2n+2

ALKENE - general formula

C_nH_2n

ALKYNE - general formula

C_nH_2n-2

HALOGENOALKANE - general formula

C_nH_2n+1X

ALCOHOL - general formula

-OH-

ALDEHYDES - general formula

-CHO

KETONE - general formula

-CO-

CARBOXYLIC ACID - general formula

-COOH

ETHER - general formula

-O-

ESTER - general formula

-COO-

AMINE - general formula

-NH₂

AMIDE - general formula

-CONH₂

NITRILE - general formula

-CN

CYCLOALKANE - general formula

C_nH_2n

CYCLOALKENE (with one double bond) - general formula

C_nH_2n-2

CYCLOALKYNE (with one triple bond) - general formula

C_nH_2n-4

ARENE (with one phenyl group) - general formula

C_nH_2n-6

ALKANE - suffix

-ane

ALKENE - suffix

-ene

ALKYNE - suffix

-yne

HALOGENOALKANE - suffix

chloro-/bromo-/…

ALCOHOL - suffix

-ol

ALDEHYDE - suffix

-al

KETONES - suffix

-one

CARBOXYLIC ACID - suffix

-oic acid

ETHER - suffix

alkoxy-

ESTER - suffix

-oate

AMINE - suffix

-amine

AMIDE - suffix

-amide

NITRILE - suffix

-nitrile

ARENE - suffix

-benzene

ALKENE - functional group

alkenyl

ALKYNE - functional group

alkynyl

HALOGENOALKANE - functional group

the halogen

ALCOHOL - functional group

hydroxyl

ALDEHYDE - functional group

aldehyde (carbonyl)

KETONE - functional group

carbonyl

CARBOXYLIC ACID - functional group

carboxyl

ETHER - functional group

ether

ESTER - functional group

ester

AMINE - functional group

amino

AMIDE - functional group

carboxamide

NITRILE - functional group

nitrile

ARENE - functional group

phenyl group

Primary

Functional group connected to one R group

Secondary

Functional group connected to two R groups

Tertiary

Functional group connected to three R groups

Structural isomers

Molecules that have the same molecular formula but different connectivities

Types of isomers

• Branched

• Straight-chain

• Position

• Functional group

Polarity ranking of the functional groups (most to least polar)

Amide>acid>alcohol>ketone~aldehyde>amine>ester>ether>alkane

Relative strength of intermolecular forces (strongest to weakest)

Hydrogen bonding>dipole-dipole>London dispersion forces

Branching … boiling point

decreases

As number of C increases, molar mass increases, so boiling point …

increases

Why are monomers gas, but polymers solid?

Monomers have smaller surface area, so weaker LDF

Two factors solubility in water depends on

1. Length of hydrocarbon chain

2. Functional group

Homologous series that are soluable in water

• Alcohols

• Aldehydes

• Ketones

• Carboxylic acids

The longer the carbon chain, the … the solubility in water

lower

Ethanol is a good solvent, because…

it contains both polar and non-polar ends

A free radical

A molecular entity that has an unparied electron, produced by homolytic fission (highly reactive)

Radicals are produced by …

homolytic fission

Electrophile

Electron-deficient species with a positive charge

Nucleophile

Electron-rich species with at least one lone pair of electrons, may have a negative charge

Homolytic fission

When a covalent bond breaks by splitting the shared pair of electrons between two products

Heterolytic fission

When a covalent bond breaks with both the shared electrons going to one of the products

Conditions required for oxidation of alcohols

Heating under reflux

Conditions required for free radical substitution

UV light

Conditions required for nucleophillic substitution

Warm, aqueous

Conditions required for hydrogenation

180^o, nickel catalyst

Conditions required for halogenation

Room temp (loss of color)

Conditions required for reaction with hydrogen halides

Room temp, in solution

Conditions required for hydration

Catalyst, phosphoric acid, high temperature, high pressure

Reagent in oxidation of alcohol

Cr₂O₇^2- (dichromate ion) and H⁺ (hydrogen ion)

What is always the product in the propagation step of free radical substitution?

A hydrogen halide

Reagent in nucleophillic substitution

usually OH^- (hydroxide ion)

Reagent in hydrogenation

H—H

Reagent in halogenation

Cl—Cl or Br—Br

Reagent in reaction with hydrogen halide

H—Cl or H—Br

Reagent in hydration

H—O—H (water)

What is hydration?

Electrophilic addtion reaction of an alkene with water

Why are alkenes susceptible to electropilic attack?

high electron density of the carbon-carbon double bond

4 types of electrophilic addition

• Hydrogenation

• Halogenation

• Reaction with hydrogen halides

• Hydration

Polymers

Macromolecules made from repeating subunits called monomers

Properties of polymers

Melt gradually, soft, non-polar, insoluable, unreactive, good insulators

3 types of polymers

• Thermoplastic

• Thermosetting

• Elastomer

Addition polymers form by…

breaking of a double bond in each monomer

Product of first oxygenation of a primary alcohol

Aldehyde

Product of second oxygenation of a primary alcohol

Carboxylic acid

Product of oxygenation of a secondary alcohol

Ketone

Color change of bromine water + alkene

Brownish orange to colorless

Color change of dichromate ion + alcohol

Orange to green