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Organic Chemistry II. University of Lincoln presentation. This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License. Aromatic Hydrocarbons.

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Organic Chemistry II

University of Lincoln presentation

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

aromatic hydrocarbons
Aromatic Hydrocarbons
  • Contain double or triple bonds, but do not show the same reactivity as other unsaturated hydrocarbons
  • Benzene: C6H6
  • Used mainly as solvents
  • Substitution rather than

Additionis favoured

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resonance structure rearrange the bonding electrons
Resonance Structure:Rearrange the bonding electrons

Delocalisation, Resonance:

Stabilise molecules, so make them less reactive

Three sp2 hybrid orbitals arrange themselves as far apart as possible

-which is at 120° on a plane. The remaining p orbital is at right angles

to them.

Each carbon atom uses the sp2 hybrids to form σ-bonds with two other carbons and one hydrogen atom.

Delocalised or Conjugated System:

π-bonding electrons can move within the molecule

Delocalised orbital clouds

6 p-orbitals

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naming aromatic hydrocarbons
Naming Aromatic Hydrocarbons

Flurobenzene

Ethylbenzene

Toluene

Aniline

-ortho

-meta

1,2-Dichlorobenzene

Benzoic acid

Phenol

1,3-Dichlorobenzene

-para

1,4-Dichlorobenzene

o-Xylene

m-Bromostyrene

2,4,6-Trinitrotoluene (TNT)

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reactions of aromatic hydrocarbons
Reactions of Aromatic Hydrocarbons

Substitution

  • Aromatic Substitution reaction – Aromatic compound loses a hydrogen atom and another atom or group takes its place.
  • It is possible for substitution to occur in more than one place on the ring.

otha-Dinitrobenzene

meta-Dinitrobenzene

para-Dinitrobenzene

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alcohols
Alcohols
  • –OH group (hydroxyl group)
  • Replace -e with -ol
  • CH3OH, methanol, simplest

alcohols are classified as primary (1°), secondary (2°), or tertiary (3°) depending on the number of carbon atoms bonded to the carbon bearing the -OH group

Primary

Alcohol (1o)

Secondary

Alcohol (2o)

Tertiary

Alcohol (3o)

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naming alcohols
Naming Alcohols

methanol

ethanol

propanol

2-ethyl-1-butanol or 2-ethyl-butan-1-ol

2-propanol or propan-2-ol or isopropyl alcohol

Polyhydroxy alcohols are alcohols that possess more than one hydroxyl group

1,2-Ethanediol

(ethylene glycol)

1,2-propanediol

(propylene glycol)

1,2,3-propanetriol

(glycerol)

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reactions of alcohols
Reactions of Alcohols

■ Reaction with acids to produce Esters

Acetic Acid

(ethanoic acid)

Ethyl acetate

■ Redox reaction (Reduction and oxidation)

Ethanol

Acetaldehyde

Acetic Acid

Alcohol Dehydrogenase

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ethers
Ethers
  • –O- group (ether group)
  • CH3OCH3, dimethyl ether simplest
  • Soluble in water- H-bonding to water - Polar
  • Flammable – Ether can cause flash fires
  • Low Reactivity – Make Good Reaction Solvents
  • Naming: alkyl groups in alphabetical order followed by ether

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aldehydes and ketones
Aldehydes and Ketones
  • Both contain a carbonyl group (C=O)

Aldehyde Ketone

Naming

Aldehydes Change -e ending to –al

ethane ethanal

(acetaldehyde)

Ketones Change -e ending to –one

propane propanone

(acetone)

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reactions of aldehydes and ketones

Tertiary

Alcohol

Secondary

Alcohol

Reduction

Oxidation

Cannot be oxidised

Reactions of Aldehydes and ketones

Synthesis: produced by oxidation of alcohol

Primary

Alcohol

Reduction

Oxidation

Reduction of carbonyl group to produce alcohols

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oxidation of carbonyl group
Oxidation of carbonyl group

Strong Oxidation

Reduction

Reduction

Oxidation

Carboxylic acid

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carboxilic acids
Carboxilic acids
  • Contains C=O and –OH group on same carbon
  • Change -e to -oicacid
  • Acetic acid: acid in vinegar
  • Simplest: methanoic acid

(formic acid)

Methanoic acid

Ethanoic acid

Propanoic acid

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reactions of carboxilic acids
Reactions of Carboxilic acids

■ Esterification reactions

Acetic Acid

(ethanoic acid)

Ethyl acetate

■ Reduction to aldehydes

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ester
Ester
  • Derived from carboxylic acids and alcohols
  • Tend to be fragrant
    • Methyl butyrate apple
    • Ethyl butyrate pineapple
  • An ester name has two parts - the part that comes from the acid (propanoate) and the part that shows the alkyl group (methyl).

Example: Methyl propanoate

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reactions of esters

R2OH

R+

Ester

H2O

Acid

R2NH

base

Amide

Reactions of Esters

Substitution

Reduction of esters

Hydrolisis of esters (basic)

Carboxylate

ester

Sodium

hydroxide

Sodium

Carboxylate

Alcohol

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amines
Amines
  • Derived from ammonia by substituting H for alkyl groups. It is an alkali
  • We have primary, secondary or tertiary amines depending on the number of H substituted

Primary amine (1o)

Secondary amine (2o)

Tertiary amine (3o)

Ammonia

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amines1
Amines

1,4-butanediamine

Putrescine (found in decaying meat) (1o)

Amphetamine

(dangerous stimulant) (1o)

Triethylamine (3o)

Isopropylamine (1o)

Piperidine

1,5-pentanediamine

Cadaverine (found in the putrefaction of cadavers

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reactions of amines
Reactions of Amines

Alkylation

Oxidation reduction

Phenylamine

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acknowledgements
Acknowledgements
  • JISC
  • HEA
  • Centre for Educational Research and Development
  • School of natural and applied sciences
  • School of Journalism
  • SirenFM
  • http://tango.freedesktop.org

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