OCR organic reaction mechanisms

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AS

Free Radical Substitution Electrophilic Addition Nucleophilic Substitution

A2

Electrophilic Substitution Nucleophilic Addition

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Free radical substitution

chlorination of methane

i.e. homolytic breaking of covalent bonds

Overall reaction equation

CH4 + Cl2
Conditions

CH3Cl + HCl

ultra violet light excess methane to reduce further substitution

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Free radical substitution mechanism

ultra-violet Cl2 Cl + Cl CH4 + Cl CH3 + Cl2 CH3 + Cl CH3 + CH3 initiation step CH3 + HCl CH3Cl + Cl CH3Cl CH3CH3 two propagation steps

termination step minor termination step

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Further free radical substitutions

Overall reaction equations CH3Cl + Cl2
CH2Cl2 + Cl2 CHCl3 + Cl2 Conditions

CH2Cl2 + HCl
CHCl3 + HCl CCl4 + HCl

ultra-violet light excess chlorine

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Electrophilic addition
bromine with ethene Overall reaction equation CH2=CH2 + Br2 CH2BrCH2Br 1,2-dibromoethane

mechanism

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Electrophilic addition mechanism

bromine with ethene H C H C H H

H
H C +

H
C Br

carbocation
H

+ Br Br Br Br

Br

H
H C Br

H C Br H

1,2-dibromoethane
reaction equation

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Nucleophilic substitution
water with bromoethane CH3CH2Br + H2O
mechanism

CH3CH2OH + HBr ethanol

hydroxide ion with bromoethane CH3CH2Br + OH- (aqueous)

mechanism

CH3CH2OH + Brethanol

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Nucleophilic substitution mechanism

water with bromoethane H + CH3 C H O H ethanol H H CH3 C H
reaction equation

H Br

CH3 C
H

+ O
H

H Br

OH

Br

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Nucleophilic substitution mechanism

hydroxide ion with bromoethane

H + CH3 C

Br

H CH3 C OH

H
OH-

H
ethanol

Br

reaction equation

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Electrophilic Substitution
Nitration of benzene

C6H6

+ HNO3

C6H5NO2

+ H2 O

Conditions / Reagents concentrated HNO3 and concentrated H2SO4

50oC

mechanism

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electrophilic substitution mechanism (nitration) 1. Formation of NO2 the nitronium ion

+

HNO3 + 2H2SO4

NO2

+ 2HSO4- + H3O+

2. Electrophilic attack on benzene

NO2 +
3. Forming the product

NO2 H

O SO3H

NO2 H O SO3H
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and re-forming the catalyst

reaction equation

Nucleophilic Addition
addition of hydrogen cyanide to carbonyls to form hydroxynitriles RCOR + HCN RC(OH)(CN)R RCH(OH)CN

RCHO + HCN Conditions / Reagents

HCN (aq) and NaOH(aq) to form the CN- nucleophile

HCN + OHCN- + H2O Room temperature and pressure
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Nucleophilic Addition Mechanism hydrogen cyanide with propanone CH3COCH3 + HCN CH3C(OH)(CN)CH3 C N CN + CH3 C CN O CH3

HCN / NaOH (aq) is a source of cyanide ions

O
CH3 C CH3 CN

CN

O
CH3 C CH3

H CN

2-hydroxy-2-methylpropanenitrile
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References
Steve Lewis for the Royal Society of Chemistry

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