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5 Introduction to organic chemistry

5.1 Carbon

Can form many compounds can form chains, branches and rings of various sizes + relative inertness and unreactiveness of their C-C, C-H bonds.

5.2 Functional groups

Functional group group of atoms which gives an organic compound its chemical properties and the part that reacts

Homologous series same general formula / same functional group / similar chemical reactions / physical properties change (bp / density) with change in length of carbon chain.

Name

Functional group

Structural

General formula

Prefix/suffix

 

formula

Alkane

C-H

CH 3 CH 2 CH 3

C N H 2N+2

-ane

Alkene

>C = C<

CH 3 CH=CH 2

C N H 2N

-ene

Halogenoalkane

C-X (halogen)

CH 3 CHBR

C N H 2N+1 Br

bromo-

Alcohol

C-OH

CH 3 CH 2 OH

C N H 2N+1OH

-ol

Aldehyde

-C-H / =O

CH 3 CHO

C N H 2N O

-al

Carboxylic acid

-C = O/ - OH

CH 3 COOH

C N H 2N+1 COOH

-oic acid

5.3 Empirical formulae the formula found by experiment simplest whole number ratio of the

atoms of different elements in a compound

1) Calculate masses 2)Calculate molar masses (g mol -1 ) 3) Calculate number of moles (mass / molar mass) 4) Divide mol by smallest number of moles 5) multiply until whole numbers

Molecular formulae shows the actual number of atoms of each element in one molecule usually found by mass spectrometry

Structural formula show in minimal detail which atoms or groups of atoms, are attached to each other in one molecule of a compound

Displayed formula shows all the atoms and all the bonds between them in one molecule of a compound

Skeletal formula - shows the functional groups fully but the hydrocarbon part of a molecule simply as lines between carbon atoms, omitting the symbols for carbon and hydrogen atoms.

Adam Clarke www.brain-freeze.co.uk

5.4 Naming organic compounds

Alkanes

1 Look for the longest unbranched chain of carbon atoms in the carbon skeleton of the molecule and name that part of the compound.

2 Identify the alkyl (alkane 1H) groups attached to the longest unbranched chain. Methyl CH3 / Ethyl CH3CH2 / Propyl CH3CH2CH2 / Butyl CH3CH2CH2CH2

3 Number the carbon atoms in the main chain to identify which carbon atoms the side groups are attached to.

4 Name the compound using the name of the longest unbranched chain, prefixed by the names of

the side groups and the numbers of the carbon atoms to which they are attached. The numbering of the carbon atoms can be from either the left or the right to give the name with the lowest numbers. 5- Where there is more than one type of side group they should be around alphabetically. 6- when there are two or more of the same side group the prefix di,ti and tetra should be added.

Alkenes Same general rules as alkane use ene / prefixed by number to indicate position of double bond

5.5 Isomerism

Structural isomers are compounds with the same molecular formula but different structural formulae

Chain isomers different chains of carbon atoms Position isomers have different positions of the same functional group Functional group isomers different functional groups

5.6 Mechanisms of organic reactions

• Homolytic bond breaking – covalent bond involves a shared pair of electrons if the bond breaks homolytically then each atom keeps one electron equal splitting (homolytic fission)

•This produces fragments with unpaired electrons called free radicals.

• These exist for a short period in a reaction, but quickly react to form new products.

• They are intermediates that form during a reaction but disappear as the reaction is completed

• free radicals often occur in reactions taking place in the has phase / in a non-polar solvent

• UV light can speed up free-radical reactions

• Free-radical processes = burning of petrol / other alkanes substitution reactions of alkanes with halogens / free-radical reactions high in atmosphere / formation/destruction of o-zone layer

Adam Clarke www.brain-freeze.co.uk

Heterolytic bond breaking When a covalent bond breaks heterolytically one atom takes both of the electrons from the bond leaving the other atom with none.

Heterolytic bond breaking (fission) produces ionic intermediates such as CH3+ and Br- , in reactions.

This type of bond breaking is favoured when reactions take place in polar solvents e.g. water.

Often the bond that breaks is already polar with positive/negative charged ends.

Some of the reagents that initiate reactions seek out the positive end of polar bonds these nucleophiles

Other reagents seek out the negative end of polar bonds or the electron dense regions in molecules these are called electrophiles.

Nucleophiles

molecules or ions with a lone pair of electrons which can form a new covalent bond

they are electron-pair donors

nucleophiles are reagents which attack molecules that have a partial positive charge

so they seek out positive charges they are nucleus loving •the substitution reaction of halogenoalkanes involves nucleophiles.

Electrophiles •these are molecules / ions that attack parts of molecules which are rich in electrons

• negative ions or negative centres, in molecules

• they are electron-loving reagents.

•Electrophiles form a new bond by accepting a pair of electrons from the molecule attacked during a

reaction. An example of an electrophiles is the H atom at the positive end of the H-Br bond in hydrogen bromide. Alkene reactions can include electrophillic addition.

Free radicals highly reactive single atoms, or groups of atoms with unpaired electrons

Nucleophiles are ions or molecules with a lone pair of electrons that attack positive ions or positive centres in molecules

Electrophiles are reactive ions and molecules which attack negative ions or negative centres in molecules.

Adam Clarke www.brain-freeze.co.uk